

‫א‬
‫א‬‫א‬

١٥٣
  ١٥٣  ‫א‬
 
 ‫א‬‫א‬ ‫א‬

 

 W،،‫א‬‫א‬،‫א‬

  ‫א‬ ‫א‬ ‫א‬ ‫א‬‫א‬  ‫א‬ ‫א‬  ‫א‬ ‫א‬ 
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K ‫א‬‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
   ‫א‬        ،‫א‬ ‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،
‫א‬         ‫א‬   ،‫א‬ ‫א‬‫א‬  
 ‫א‬ ‫א‬ ‫א‬‫א‬  ‫א‬ ‫א‬ ‫א‬  ‫א‬ ‫א‬  ‫א‬ ‫א‬
‫א‬ ‫א‬‫א‬،‫א‬
 K‫א‬‫א‬،‫א‬

?‫א‬??‫א‬‫א‬?‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬     ،‫א‬ ‫א‬ ‫א‬‫א‬      
 K‫א‬‫א‬‫א‬‫א‬‫א‬

   ‫؛‬    ‫א‬ ‫א‬  ‫א‬    ‫א‬
 K‫א‬

 ‫א‬‫א‬‫א‬‫א‬
 
  ١٥٣  ‫א‬
 
 ‫א‬‫א‬ ‫א‬

 
‫א‬‫א‬، KK‫א‬‫א‬‫א‬‫א‬ 
‫א‬،‫א‬‫א‬
 ‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
–‫א‬‫א‬–‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
، ، ‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬
‫א‬K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬، ‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
K
 ‫א‬‫א‬‫א‬
 ،‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬

 

١
  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
،‫א‬‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬ -١
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ -٢

 W‫א‬‫א‬‫א‬
 K٪٨٠‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K‫א‬

 W‫א‬‫א‬
 KOverhead Projector
K‫א‬‫א‬

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

-١-
  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

 W١ J١
K‫א‬  ‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬Organic
 ،،‫א‬‫א‬،‫א‬
K‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬K‫א‬
F‫א‬‫א‬1828 Wohler‫א‬‫א‬‫א‬‫א‬
، ‫א‬‫א‬E‫א‬
 W‫א‬‫א‬

O

 NH4OCN H2N C NH2

‫א‬‫א‬‫א‬، ‫א‬،‫א‬ 
 K‫א‬،
‫א‬‫א‬، ‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬

 ‫א‬‫א‬‫א‬‫א‬‫א‬K
 K‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬ ‫א‬،‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
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  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

،
 ‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬KFunctional Groups‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬E–OHF ‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬Ksp3
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

 WFunctional Group‫א‬‫א‬٢ J١
‫א‬‫א‬‫א‬‫א‬‫א‬ 
،،‫א‬ ‫א‬K‫א‬‫א‬‫א‬
O

‫א‬ ‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬ C H

 W‫א‬‫א‬‫א‬‫א‬
 
O
[O]
O CH3C-OH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3C H
[H]
CH3CH2OH ( ‫) ﻏﻮل‬
  ‫أ‬ 
 
[O]
O CH3CH2COOH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3 CH2C H
[H]
CH3CH2CH2OH ( ‫) آﺤﻮل‬
  ‫ب‬
 
[O]
O CH3CH2CH2COOH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3CH2CH2C H
[H]
CH3CH2CH2CH2OH ( ‫) آﺤﻮل‬
‫ج‬
   
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫ ( א‬-CHO) ‫א‬‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
، ‫א‬‫א‬
FK‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬E١ J١

 ‫א‬‫א‬WE١ J١F

 ‫א‬  ‫א‬‫א‬
 
 ‫א‬‫א‬  ‫א‬

 ‫א‬
 H2C C H2 C=C

 ‫א‬‫א‬
 E‫א‬‫א‬F
  
 ‫א‬ C C
 H C C H 
X
Br
 ‫א‬‫א‬‫א‬ C
CH3I ,
 
( X = I, Br, Cl , F )
 ‫א‬
 CH 3CH2OH C OH

 ‫א‬‫א‬ O C
 CH3 O CH3 C

O O
 ‫א‬‫א‬
 CH3 C H  C H
O O
 ‫א‬
C C C
 CH3 C CH3 
O O
‫א‬‫א‬
 H C OH  C OH

-٤-
  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

‫א‬ O
O
 ‫א‬ C Y
 CH3 C OCH 3 ( Y = Cl ,OR, NR 2 ,...)
CH3
 ‫א‬ C N
 CH3NH2 , CH3NH 
 ‫א‬
 CH3CN C C N

NO 2 O
CH 3NO 2 ,  
C N O-
 
 ‫א‬ C SH
 CH3SH

 W‫א‬‫א‬‫א‬٣ J١
K‫א‬‫א‬EF‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬?hemolytic?‫א‬K‫א‬
K‫א‬‫א‬‫א‬?heterolytic?،
 K X‫א‬‫א‬‫א‬‫א‬‫א‬
 
.
C . .X C. + X " ‫" أﻧﻔﺼﺎم ﻣﺘﺠﺎﻧﺲ‬

  ‫ﺟﺬر ﺣﺮ‬
 
 

-٥-
  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

}
C . .X C + + .. X

‫أﻳﻮن آﺮﺑﻮﻧﻴﻮم‬
carbonium ion
" ‫" اﻧﻔﺼﺎم ﻏﻴﺮ ﻣﺘﺠﺎﻧﺲ‬

_
C . .X C .. + X +

‫أﻳﻮن آﺮﺑﺎﻧﻴﻮن‬
  carbanion
 
 ‫א‬K ،‫א‬‫א‬‫א‬ 
‫א‬K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
X‫א‬،‫א‬‫א‬‫א‬ ‫א‬ 
K
 ‫א‬،‫א‬
‫א‬‫א‬ ‫א‬‫א‬‫א‬
K ‫א‬‫א‬X‫א‬E‫א‬F‫א‬‫א‬
KX‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬
‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬‫א‬

 ‫א‬، E‫א‬F‫א‬
K‫א‬‫א‬NucleophilesENu-F‫א‬ElectrophilesEE+F
E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WK‫א‬

H+ , Br+ , NO2+ , BF3 , AlCl3

 
F‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WKE
-٦-
  ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

 
. ._. . . _. . . _. . . _. ..
HO . , RO . , RS . , CN . , H2O .. , R2N ..
  .. .. ..
 
 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W،‫א‬
‫א‬،substitution‫א‬‫א‬‫א‬  J١
K‫א‬

 CH3CH 2OH + HBr CH3CH2Br +H2O

 E‫א‬‫א‬F

‫א‬‫א‬‫א‬Waddition‫א‬   J٢
K  ‫א‬‫א‬‫א‬‫א‬‫א‬

 CH 2 CH2 + Br2 CH2BrCH 2Br

 EF

‫א‬،eliminationE‫א‬F‫א‬‫א‬  J٣
‫א‬‫א‬F ‫א‬‫א‬‫א‬‫א‬
 KE
 
 CH 3CH 2Br + NaOH CH2 CH2 + H2O + NaBr
 E‫א‬‫א‬F
 
 
 
 

-٧-
 ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W١
 
CH2OH
_
‫ب‬ O
‫ ح‬- O
   CH 3C N(CH 3)2 ‫أ‬
 
CH3
_ _ CH3 Pb CH3 ‫د‬
 CH3CH2F ‫و‬ ‫هـ‬
  CH3

O
   
‫ج‬
CH 3OCH 2CH 2C H
 
 
 ‫؟‬‫א‬،‫א‬‫א‬‫א‬W٢
 

+ - -
 CH3CH2 , ZnCl2 , F , CH3CH2 , CH3OH , CH3SH , CH3NH2
 
W‫א‬‫א‬W٣
O
a) - CH3 C H + CH3MgI CH3CHCH3

 OMgI

b) - CH3CH2I + NaSH CH3CH2SH + NaI

c) - CH2 CH CH 3 + HCl CH3CHCH 3

 Cl

-٨-
 ‫א‬‫א‬  ١٥٣  ‫א‬
   ‫א‬‫א‬ ‫א‬

 ١ J٤‫א‬‫א‬
  W ١ 
  J J J J‫א‬
 
 W٢
 K‫א‬‫א‬WCH3NH2
 K‫א‬WCH3OH
 KWF-
 KW ZnCl2

 
 K‫א‬‫א‬‫א‬‫א‬W٣
 K‫א‬‫א‬
 

-٩-
 ‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬

٢
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬
  JW‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬ .٢
،E،،F‫א‬‫א‬‫א‬‫ א‬.٣
K‫א‬‫א‬

 W‫א‬‫א‬‫א‬
 K٪٨٥‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K٨

 W‫א‬‫א‬
 KOverhead Projector .١
K‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
K .٤

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬١ J٢
 ‫א‬‫א‬ 
 W

 W‫א‬ J
‫א‬‫א‬‫א‬ 
 W‫א‬K‫א‬‫א‬–‫א‬‫א‬،
–‫א‬،saturated‫א‬‫ א‬K
 Ethane CH3-CH3alkanes‫א‬
، J ‫א‬،unsaturated‫ א‬K
W
،EC=CF–‫א‬‫א‬،alkenes‫ א‬ J١
،EC C F–‫א‬‫א‬alkynes‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K
، ‫א‬Aromatic Hydrocarbons‫א‬‫א‬‫ א‬ J٢
 KC10H8‫א‬‫א‬‫א‬

 WAlkanes‫א‬٢ J٢
،‫א‬‫א‬‫א‬،‫א‬ 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

 ‫א‬‫א‬‫א‬
nCnH2n+2W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬K‫א‬‫א‬EnFEKKKKKKK،٤{٣{٢{١=nF

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 ‫א‬، ‫א‬،‫א‬

 K‫א‬

 W‫א‬١ J٢ J٢
‫א‬‫א‬‫א‬،E-aneF‫א‬‫א‬ 
E-aneF‫א‬‫א‬E‫א‬F‫א‬‫א‬
 E١ J٢F،

 ‫א‬E١ J٢F

n  ‫א‬‫א‬ ‫א‬

1 methane   CH4 
2 ethane   CH3CH3  
3 propane   CH3CH2CH3 
4 butane    CH3CH2CH2CH3
5 pentane   CH3(CH2)3CH3
6 hexane   CH3(CH2)4CH3
7 heptane   CH3(CH2)5CH3
8 octane   CH3(CH2)6CH3 
9 nonane   CH3(CH2)7CH3
10 decane   CH3(CH2)8CH3 
 
CH2‫א‬‫א‬‫א‬‫א‬ 
 ‫א‬‫א‬،Methylene‫א‬
 W‫א‬‫א‬
 Butane C4H10W‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH3 CH CH3
 CH3-CH2-CH2-CH3
 n-Butane   CH3
 Isobutane J

 Pentane C5H12 W‫א‬‫א‬

 
  CH 3
CH3 CH CH2 CH3 CH 3CH 2CH 2CH 2CH 3 CH 3 C CH 3
 
CH3   CH 3
  
  J
 –  – Neopentane
Isopentane N-pentane
 WAlkyl Group ER-F‫א‬
‫א‬‫א‬ER-F‫א‬ 
‫א‬ ‫א‬،methylCH3-‫א‬
‫א‬‫א‬‫א‬‫א‬E 2-2F‫א‬KEthylECH3CH2-F‫א‬
 ‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 K‫א‬‫א‬١٠ J٢‫א‬
‫א‬‫א‬
 ‫א‬‫א‬  ‫א‬
 ‫א‬
 Methyl  CH3 J  MethaneCH4
 Ethyl  CH3CH2- Ethane CH3CH3
Propane
N-Propyl  CH3CH2CH2-
CH3CH2CH3
 
Isopropyl   CH3-CH-CH3  CH3CH2CH2CH3
n-Butyl  CH3CH2CH2CH2-
sec- Butyl  CH3CHCH2CH3  n-Butane 

CH3
 Isobutyl _
  CH 3 CH CH 2
  CH3
 
     CH3 CH CH3
     
Tert-butyl CH3  Isobutane
  CH3 C  
  CH3
 
WCycloalkanes ‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
CH 2

 CH 2 CH 2
   Cyclopropane
 
 
   
CH2 CH2

  CH2 CH2
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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

   
 Cyclobutane
 
   
  CH2
CH2 CH2
CH2 CH2
   
 Cyclopentane
 
 
CH2CH3
  
 Ethylcyclobutane
 WIUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
  IUPAC W‫א‬‫א‬،‫א‬‫א‬
International Union of Pure and Applied Chemistry.

W‫א‬‫א‬
E‫א‬F‫א‬‫א‬‫א‬‫א‬ E١
 K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ E٢
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬K ‫א‬‫א‬‫א‬
،
 ‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬E JF
‫א‬‫א‬‫א‬ane‫א‬
W‫א‬‫א‬yl
 
1 2 3 4 5 6
CH 3 CH 2 CHCH 2 CH 2 CH 3

  CH 2 CH 3
 
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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

  3-Ethylhexane
E‫א‬‫א‬
 F‫א‬‫א‬‫א‬‫א‬‫א‬  
‫א‬penta ،tetra،tri،di‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬KKKKKK،،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
 W‫א‬‫א‬‫א‬
 
CH3
CH3 CH CH2 C CH
5 4 3 3 2 1
  CH3 CH3
 
2-2-4-Trimethylpentane
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  
 W‫א‬‫א‬
 
CH2CH3
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH CH C CH2 CH3
_
  CH3 CH2 CH2 CH3 CH2CH3
 
  3,3-Diethyl-4-methyl-5-n-propyloctane
 
‫א‬‫א‬‫א‬  
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 
7 6 5 4 3 2 1
CH 3 CH 2 CH CH 2 CH CH 2 CH 3
  CH 3 CH 2CH 3
 
3-Ethyl-5-Methylheptane
 

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬E‫א‬F‫א‬‫א‬  
،EaneF‫א‬EylF‫א‬،‫א‬
‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬
CH3 CH3
1' 2' _
3 CH CH CH3
CH3 CH2 CH CH CH2 CH2 CH2 CH3
1 2 4 5 6 7 8
CH2 CH2CH3
  CH3
 
 3-Ethyl-4(1',2',Dimethylpropyl) nonane
 
E‫א‬F‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬
 W‫א‬E‫א‬

F: Fluoro NO2W Nitro

 ClW Chloro NH2W Amino

BrW Bromo CNW Cyano

 IW Iodo    

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

W
Br
5 4 2 1
CH3CHCHCH 2CH3
3
CH3 Cl
 3-Bromo-2-chloro-4-methylpentane
 
‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬‫א‬‫א‬neo-‫א‬iso-
‫א‬‫א‬tridisec-tert-‫א‬‫א‬‫א‬
 K‫א‬

 W‫א‬‫א‬‫א‬‫א‬٢ J٢ J٢
‫א‬،nonpolar‫א‬ 
C5‫א‬،‫א‬‫א‬‫א‬‫א‬C4C1،‫א‬‫א‬
١٨‫א‬‫א‬‫א‬‫א‬،C17
‫א‬، ‫א‬ ‫א‬، ‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬E‫א‬‫א‬F
 K

 W‫א‬‫א‬‫א‬٣ J٢ J٢
‫א‬‫א‬،‫א‬‫א‬ 
 W‫א‬‫א‬

 Wcombustion ‫א‬‫א‬ -١
–‫א‬‫א‬‫א‬ 
 K‫א‬K‫א‬‫א‬‫א‬
- ١٨ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH4 + 2O2 CO2 (g) + 2H2O + ‫ﻃﺎﻗﺔ‬

  (g)
 WHalogenation‫א‬ -٢
 ‫א‬Br2‫א‬Cl2‫א‬E‫א‬‫א‬F‫א‬
، 
‫א‬‫א‬‫א‬‫א‬،‫א‬
 ‫א‬
 W‫א‬‫א‬،

 WE١F
Br

+ Br2 + HBr

  Bromocyclopentane
 

 WE٢F
H
hν
H C H + Cl 2 H3C _ Cl + HCl
H Chloromethane

hν  
CH3 Cl + Cl2 CH2Cl2 + HCl
 Dicarbomethane
 
hν
hv
CH 2Cl2 + Cl2 CHCl 3 + HCl
 Chloroform

hν

- ١٩ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

hv
C H Cl 3 + Cl2 C C 14 + HCl
Carbontetrachloride'

،‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬
 W

 K‫א‬EF‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬
 

H 2 /Pt ,Pd ‫ أو‬Ni _ _ _

C C C C
‫ﺿﻐﻂ‬
H H

  Alkene Alkane
 
H2 , Pt
CH3CH2CH2CH2CH = CH 2 CH3CH2CH2CH2CH2CH2
‫ﺿﻐﻂ‬

1- Hexene n- Hexane

 W K
،‫א‬‫א‬،‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬  KGrignard reagents‫א‬
 K‫א‬‫א‬
 
‫اﻳ ﺜﺮ ﺟ ﺎف‬
R-X + Mg RMgX

 Alkyl halide Alkyl magnesium halide 

- ٢٠ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬
R-MgX + H 2O RH + Mg(OH)X
  Alkane
RMgX+CH 3OH RH + Mg(OCH 3)X
  Alkane
Br Mg Br
‫اﻳ ﺜﺮ ﺟ ﺎف‬
CH3CH2CHCH 3+Mg CH3CH2CHCH 3

Mg(OH)Br + CH 3CH2CH2CH3 H2O

 

 W K
 K‫א‬‫א‬‫א‬
 
2R - X + 2 Na R - R + 2 NaX
  Alkane

 2 CH 3 CH2 Cl + 2 Na CH3 CH2 CH2 CH3

 W‫א‬‫א‬‫א‬‫ א‬K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬
 W‫א‬‫א‬Lithium dialkyl copper ( R2CuLi)
 
(CH 3 CH2)2 CuLi + CH 3 CH2 CH2 Br

  CH3 CH2 CH2 CH2 CH3 + CH3 CH2 Cu + LiBr

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
 W‫א‬‫א‬‫א‬‫א‬

 CH3 CH2 Cl + Li CH3 CH2 Li

 

 2 CH 3 CH2 Li + Cul (CH 3 CH2)2 CuLi + Lil

 W‫א‬٤ J٢ J٢
K ‫א‬،
 ‫א‬‫א‬‫א‬‫א‬‫א‬ 
K ‫א‬‫א‬‫א‬
  ‫א‬‫א‬،
 ‫א‬‫א‬٪٨٠‫א‬
 K‫א‬،‫א‬‫א‬
‫א‬‫א‬KRefining‫א‬‫א‬
 K

 Walkenes‫א‬٣ J٢
،EC=CF–‫א‬‫א‬ 
،CnH2n‫א‬‫א‬‫א‬،olefins
 KC2H4‫א‬‫א‬CnH2n-2‫א‬
 
H 120 H
C = C
 H H
 
 
 
 
 
 
- ٢٢ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬١ J٣ J٢

W‫א‬‫ א‬K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
،‫א‬‫א‬–ylenealkane‫א‬‫א‬‫א‬  ‫א‬–ane
 W‫א‬‫א‬

 K‫א‬‫א‬E1-3-2F

Alkene‫א‬  Alkane‫א‬

 Ethylene CH 2=CH 2 Ethane CH3CH3

 
 Propylene CH3-CH =CH2
   Propane CH 3CH 2CH 3
Butylene CH 3CH 2CH=CH 2  

 2-Butylene CH 3CH=CHCH 3  
 
n-Butane CH 3CH 2CH 2CH 3
Isobutylene CH3 CH = CH2 Isobutane CH3 CH CH3

  CH3  CH3
– CH2=CH2‫א‬‫א‬‫א‬‫א‬
 W( Vinyl group )‫א‬CH=CH2
 
CH2 = CH CH 2 = CH CH2 = CH

Cl Br
 Vinyl Chloride  Vinyl bromide 
Vinyl Cyclohexane
 
 W( allyl group)‫א‬CH3CH=CH2‫א‬‫א‬‫א‬

- ٢٣ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH2CH = CH2
Cl
  Allyl Choride

WIUPAC‫א‬‫א‬ K
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ 
  ‫א‬E‫א‬‫א‬FIUPAC‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KE‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬  E٣
–‫א‬‫א‬‫א‬ ‫א‬–ane‫א‬‫א‬‫א‬‫א‬ E٤
Kene
 ‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ E٥
K‫א‬
‫א‬‫א‬‫א‬،
 ‫א‬‫א‬‫א‬
W‫א‬‫א‬،‫א‬‫א‬‫א‬
 
5 4 3 2 1
CH3CH-CH = CH-CH3

CH3
 4- Methyl - 2- Pentene
 
 W‫א‬‫א‬‫א‬
    CH3CH2CH = CH2
CH2 = CH2 CH 3 -CH = CH 2   1-Butene
 
  Ethene   Propene
   

- ٢٤ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH2-CH = CH2

Cl
 2-Ethyl-1-Butene   3-Chloro -l- Propene
 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬K ‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬
6
3
5 1 4 2
4 2
3 5 1
6
Cyclohexene 3-Methylcyclohexene
 (1-Cyclohexene‫)وﻟﻴﺲ‬ (6-Methylcyclohexene ‫)وﻟﻴﺲ‬

–ene‫א‬‫א‬‫א‬‫א‬KKKKKKtetra،tri ،di ‫א‬

‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬
 
 
4 3 2
5
5
CH2 = CH-CH 2-C-CH 2CH3 1 4
1 CH 2
2 3
  2-Ethyl,1,4-Pentadiene  1,3-Cyclopentadiene
 
 
2 4 6
1 3 5 7
  1,3,6-Heptatriene 
 
‫א‬F‫א‬‫א‬‫א‬‫א‬  
‫א‬E2-butane 1-butene‫א‬‫א‬‫א‬
- ٢٥ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
W2-butene
   
H CH3 CH3 CH3

C C C C
H H
CH3 H
  Cis-2-butene 
  trans-2-butene   
 
E‫א‬‫א‬‫א‬‫א‬F‫א‬‫א‬ 
F‫א‬‫א‬،E–cisF‫א‬،‫א‬
‫א‬‫א‬،‫א‬‫א‬Ktrans‫א‬E‫א‬
 K ٠{٩trans-2-butene٣٧،‫א‬،cis-2-butene ،‫א‬

 W‫א‬‫א‬‫א‬٢ J٣ J٢
‫א‬‫א‬ ‫א‬ ‫א‬‫א‬‫א‬‫א‬ 
،‫א‬،‫א‬،‫א‬‫א‬
 ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬ 
 ‫א‬،‫א‬
 K‫א‬

 W‫א‬٣ J٣ J٢
 W‫א‬‫א‬
W‫א‬‫א‬‫א‬‫א‬ E٦
‫א‬‫א‬‫א‬‫א‬،H+،‫א‬ 
KH3PO4‫א‬H2SO4‫א‬‫א‬

- ٢٦ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
H H H H
+
H ,
H C C H C C + H2O
OH H H H

(‫آﺤﻮل )اﻳﺜﺎﻧﻮل‬ (‫اﻟﻜﻴﻦ )اﺛﻴﻠﻴﻦ‬

 
 
‫א‬F‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ 
،
 ‫א‬‫א‬E‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬

H+,
CH2 CH CHCH3 CH3-CH = CHCH3
H OH H 2-Butene

+ + H2O
2-Butanol
CH2 = CHCH2CH3

 1-Butene

W‫א‬‫א‬‫א‬‫א‬ E٧
 KKOH‫א‬‫א‬( I , Br, Cl =X ) HX 

KOH / ‫آﺤﻮل‬ + -
CH2 CH2 CH2 = CH2 +K +CI +H2O
H Cl ‫اﺛﻴﻠﻴﻦ‬

  ‫آﻠﻮرو اﻳﺜﺎن‬ 
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬
 


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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

KOH / ‫آﺤﻮل‬
CH2 CH CH CH3 CH3 CH = CH CH3 + K+

H Br H
 
  J٢EF J٢
 
 HCH2 = CHCH2CH3+Br-+H2o
 EF  J١
 
 W‫א‬ H2SO4‫א‬‫א‬ K١
‫א‬‫א‬ ،‫א‬‫א‬‫א‬ 
‫א‬K‫א‬‫א‬
  ‫א‬‫א‬‫א‬،‫א‬
 K
 
CH2 = CH2 + H2SO4 ‫ﻣﺮآﺰ‬ CH2 CH2

H OSO3H
 ‫آﺒﺮﻳﺘﺎت اﻻﻳﺜﻴﻞ اﻟﻬﻴﺪروﺟﻴﻨﻴﺔ‬ 
 
 WPolymerization‫ א‬K٢
‫א‬––‫א‬
  
،‫א‬‫א‬‫א‬‫א‬Kpolymers‫א‬
K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬W
 ‫א‬Naphtha fraction‫א‬‫א‬‫א‬‫א‬ 
‫א‬١٠ J٤‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬،٩٠٠ J٧٠٠‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬
، ( Cr2O3+Al2O3)‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬

Cr2O3 +Al2O3
CH3CH2CH3 CH2 = CHCH3
700cْ 
 
 
 W( X = Cl ,Br, I ) HX‫א‬
 

C C + HX C C
H X
  ‫هﺎﻟﻴﺪ اﻟﻜﻴﻞ‬ 
 
CH2=CH2 + HCI CH 3 CH2 CI
  (‫آﻠﻮرو اﻳﺜﺎن )آﻠﻮرﻳﺪ اﺛﻴﻞ‬ 
 
‫א‬،‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬Markovnikov's Rule 
CH2 = CHCH3 + HCl CH2 CH CH3

  H Cl
 
   J٢
 
 WHydration ‫א‬

- ٢٩ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬K‫א‬H+‫א‬‫א‬‫א‬ 
 K
+
H
CH2 = CHCH3 + H2O CH2 CH CH3

  H OH 
 
   J٢

 W‫א‬٤ J٣ J٢
‫א‬K،‫א‬‫א‬‫א‬ 
 W‫א‬K‫א‬‫א‬

 WHydrogenation‫ א‬.١
 K‫א‬CatalystsE‫א‬FPdNi Pt ‫א‬‫א‬
Pt or Ni
CH2 = CH2 + H2 CH3 CH3
  ‫اﺛﻴﻠﻴﻦ‬ ‫إﻳﺜﺎن‬
 
،‫א‬‫א‬‫א‬،‫א‬‫א‬ 
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

 WHalogenations‫ א‬.٢
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
 

C C + X2 / CCI4 C C

 (X = CI , Br) X X 

- ٣٠ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
CH2 = CH2 + Br2 / CCI4 CH2 CH2

 Br Br 
 
،E ‫א‬‫א‬‫א‬F‫א‬‫א‬‫א‬
 
 ‫א‬ ‫א‬ 
 K‫א‬‫א‬‫א‬

 WAlkynes‫א‬٤ J٢
 JF–‫א‬‫א‬ 
‫א‬‫א‬‫א‬،CnH2n-2‫א‬‫א‬KE JC C
،‫א‬sp‫א‬‫א‬،‫א‬‫א‬،C2H2
‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬‫א‬،٣٠٠٠‫א‬‫א‬
 K‫א‬
CaO‫א‬‫א‬‫א‬ 
 K‫א‬CaS2‫א‬،

2500 oC
3C + CaO CaC2 + CO

CaC2 + 2H2O C2H2 + Ca(OH)2

 W‫א‬١ J٤ J٢
EIUPAC‫א‬F‫א‬‫א‬‫א‬‫א‬ 
‫א‬ ‫א‬، ‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،
 W‫א‬‫א‬–ene ‫א‬–yne

HC CH CH3C CH CH3CH2C CH

- ٣١ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

Acetylene Methyl acetylene Ethyl acetylene 

Ethyne 1- Butyne 

 Propyne

 WIUPAC‫א‬‫א‬

CH3 CH3
CH3C CCH3
CH3CH CH C C CH2CH CH3
2-Butyne
Cl
3-Chloro-2,7-dimethyl-4-octyne

CH C C CH
1,3-Butadiyne
 
‫א‬‫א‬ ‫א‬‫א‬ 
‫א‬‫א‬–yne‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 Kalkene‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

HC C CH2 CH CH2

1-Penten-4-yne

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬–yne ‫א‬

 W‫א‬‫א‬‫א‬٢ J٤ J٢
‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬،‫א‬K‫א‬‫א‬

- ٣٢ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬C17‫א‬C16C4 ‫א‬،
 ‫א‬C4C2
 K

 W‫א‬٣ J٤ J٢
‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬

Dehydrohalgenation W‫א‬‫א‬‫א‬‫א‬ .١

 W
 
KOH
CH3CH CH H [ CH3CH = C H]
EtOH
Br Br Br
1,2-Dibromopropane Allylbromide

NaNH2 /
CH3 C C H
Propyne

 W‫א‬‫א‬ .٢
 W‫א‬‫א‬‫א‬‫א‬
- liq NH 3
HC C Na+ + CH3Br HC C CH3 + NaBr

- liq NH3
HC C Na+ + CH3CH2I HC C CH2CH3 + NaI

- liq NH3
CH3 C C Na+ + CH3CH2Br CH3 C C CH2CH3 + NaBr
Sodium propynide

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬  J١
W‫א‬‫א‬‫א‬‫א‬

CH4 + O2 2HC CH + 2CO + 10H2

‫א‬‫א‬‫א‬‫א‬W‫א‬  J٢
،‫א‬‫א‬‫א‬‫א‬،‫א‬
E‫א‬F‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
W‫א‬

CaCO3 CaO + CO2

 Calcium carbonate

2500
CaO + 3C CaC2 + CO
Coke Calcium carbide

25ْC
CaC2 + 2H2O HC CH + Ca(OH)2
Acetylene

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  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬٥ J٤ J٢
 W‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬ .١
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬،‫א‬

R R
Pd or Ni H2\Ni
R C C R + H2 C=C RCH2CH2R
H H
 
Ni-
 ‫א‬‫א‬‫א‬‫א‬
Linders catalyst Pd + Pb(OAc)4‫א‬‫א‬‫א‬B2
 KPd/CaCO3)

 W‫א‬‫ א‬.٢
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬‫א‬

Cl Cl Cl

CH3 C C CH3 + Cl2 CH3 C = C CH3 CH3 C C CH3

Cl Cl Cl
1,1,2,2-Tetrachlorobutane

- ٣٥ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬ .٣
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 ‫א‬‫א‬‫א‬‫א‬‫א‬،
 K‫א‬‫א‬‫א‬‫א‬‫א‬

Cl
HCl HCl
CH3 C CH CH3C = CH2 CH3 C CH3
Cl Cl
2,2-Dichloropropane

 W‫א‬ .٤
‫א‬‫א‬‫א‬‫א‬ 
‫א‬، mercuric sulfate ‫א‬
 K‫א‬‫א‬

O
H H
HgSO4
CH CH + H2O C=C CH3 C H
H2SO4
H OH

Enol Acetaldehyde

OH O
HgSO4
CH3 C CH + H2O CH3 C = CH2 CH3 C CH3
H2SO4

 Acetone

- ٣٦ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬ .٥
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬‫א‬

O O
-
1)KMnO4 /OH
- R C C Rَ
2)H2O / OH
O O
-
1)KMnO4 /OH
R C C Rَ R C OH + Rَ C OH
2) 100ْC / H +

1)O3
RCOOH + RَCOOH
2)H2O /Zn Or H2O2

 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬٦ J٤ J٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬(PVC)  ‫א‬‫א‬
‫א‬‫א‬A‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KPayragyline‫א‬‫א‬
 
 
 
 
 
 
 

- ٣٧ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 2-5
 
 WIUPAC‫א‬‫א‬‫א‬‫א‬ J١
 
CH3CHCHCHCH3
-‫ب‬ CH 3 -C(CH 3 ) 2 CH 3  J
  Br Cl CH3
CH3
CH3CH2CH2 C = CH2
 J  J

C2H5
CH3
 J CH C CH  J
CH3
CH3 C = C CH3
 J
CH3 Br
 
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬–٢
 

2-bromo-2-methyloctane 2 , 3 - d i m e t h y l b u t a n e  J
J
2-chloro-3-methyl-2-pentene  J 1 , 1 - d i m e t h y l c y c l o h e x a n e  J
2 , 2 - D i b r o m o - 3 - h e x y n e  J 2,3Dimethyl-1,4-cyclohexadiene  J

 ‫؟‬‫א‬C6H14‫א‬‫א‬‫א‬‫א‬‫א‬–٣
 
 ‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬–٤
 W‫א‬‫א‬–٥

- ٣٨ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH3CH3 + Cl2 hυ
 J

C H 4 + 2 O 2  J
C H 3 C H 2 C l + N a  J

CH3CH2OH H+,∆
 J

Pt or Ni / H
2 2 CH=CH3CH  J
C C l
4 2 + B r 3 C H = C H C H 3 C H  J
CCl4
+ Cl2  J

KOH NaNH2 /
CH3CH CH CH3  J
EtOH

Br Br
CH3 C C CH3 + 2Cl2  J
Hg SO 4
CH3 C CH H2 O
H2SO4  J

 W،–٦
 
i ) C H 3 C H 3i i ) C H 3 C H 2 C l iii) CH2 = CH2

 W‫א‬‫א‬‫א‬–٧
3 - B r o m o - 1 - p e n t y n e ,4 - M e t h y l - 2 - h e x e n e

 W‫א‬‫א‬‫א‬
+
H 2 , B r 2 / H 2 O , H 2 O / H , H C l

 

- ٣٩ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 ٢ J٥‫א‬
  W١ 
2,2- Dimethyl Propane -‫ا‬ .١

3-Ethyl-1-Methyl cyclohexane -‫ﺟـ‬ .٢

3-Methyl -1- butyne -‫هـ‬ .٣

 2- Bromo -3-Methyl -2- butene J

 W٢
(‫أ‬
CH3 - CH -CH -CH3

CH3 CH3
(‫د‬
CH 3 C C CH 2CH 3
Cl CH 3
(‫و‬
Br
CH 3 C C CH 2CH 3
Br
 K‫א‬‫א‬‫א‬W٤
  W ٥ 
CH 4 +2O 2 CO2 + 2H2O + ‫ﻃﺎﻗﺔ‬ .١    J 
+
CH 3 CH2 OH
H ,
CH 2 = CH 2 + H2O .٢   J 
CCI4
CH 3 - CH = CH - CH 3 + Br2 CH2CH - CH CH 3
  J 
Br Br .٣
- ٤٠ -
 ‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬

٣
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
،‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫ א‬.٣
K‫א‬‫א‬CH2 = CHCH2CH3 .٤

 W‫א‬‫א‬‫א‬
 K٪٩٠‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K٤

 W‫א‬‫א‬
 KOverhead Projector .١
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
K .٣

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

- ٤١ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W١ J٣
‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 ‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
E‫א‬‫א‬‫א‬‫א‬F‫א‬EAromatic) ‫א‬‫א‬ 
، JOCH3  ‫א‬‫א‬‫א‬
 JC6H5‫א‬‫א‬ J J J J JCOOCH3، JCOOH
، JC6H5‫א‬‫א‬‫א‬
EF‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬

 W‫א‬٢ J٣
‫א‬‫א‬‫א‬‫א‬‫א‬C6H6‫א‬ 
‫א‬،‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬K ‫א‬sp2‫א‬‫א‬،‫א‬‫א‬‫א‬
C=C‫א‬‫א‬‫א‬، (A˚١٣٩F‫א‬‫א‬–
‫א‬‫א‬KE١٥٤A˚)C-C‫א‬‫א‬‫א‬،E١٣٢A˚)
 WKekule ‫א‬‫א‬

 
 I II
‫א‬Hybrid‫א‬‫א‬KII،I‫א‬ 
‫א‬‫א‬‫א‬‫א‬KII،I
 Delocaized

- ٤٢ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬٣ J٣
 W‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ K١
FP‫א‬‫א‬‫א‬EF
KE‫א‬
K‫א‬ K٢
K‫א‬‫א‬‫א‬ K٣
‫א‬‫א‬‫א‬EHuckels ruleF K٤
En = 0,1,2,3KKKKKKKFE4n+2)‫א‬‫א‬π‫א‬‫א‬
‫א‬Eπ‫א‬F‫א‬‫א‬
WE٦F‫א‬‫א‬E١Fn‫א‬
 
 (4x1+2) = 6

E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬
 

    
 Benzen Naphthalene Anthracene
 n =1 n =2 n =3

..
N
N  
  .. Pyrole
 Pyridine n =1
- ٤٣ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

n =1 4(1)+2=6 πes
 Phenanthrene 4(1)+2=6 πes
n=3
 4(3)+2=14 πes
+
+ -

   
 n = 0  n =1  
4(0)+2=2 πes n =1
4(1)+2=6 πes
4(1)+2=6 πes

 W‫א‬‫א‬‫א‬
 
- +

 W‫א‬‫א‬‫א‬٤ J٣
‫א‬‫א‬º٨٠K‫א‬،‫א‬‫א‬
 ‫א‬‫א‬ ‫א‬‫א‬º٤{٥

‫א‬ 
 Kπ‫א‬‫א‬

 W‫א‬٥ J٣
 ‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬
W‫א‬‫א‬‫א‬‫א‬‫א‬ K١
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

- ٤٤ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 

Br I CH2CH3

     
Bromobenzene Iodobenzene Ethylbenzene
NO2

 
Nitrobenzene
 W‫א‬

CH3 CH=CH2 CH _ CH _ CH CHO

3 3

     
Toluene Styrene  Cumene Benzaldehyde

O
OH COOH NH2
C _ CH3

    
Phenol Benzoic acid   Aniline
Acetopnenone

SO3H OCH3

   
Anisole
Benzenesulfonic acid

- ٤٥ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬،‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬phenyl
CH3CHCH2CH3 CH2CH2OH

   
 2-Phenylbutane 2-Phenylethanol
Benzyl‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬،Benzal‫א‬‫א‬
 KBenzo
 
CH2Cl CHCl2 CCl3

     
Benzylchloride  Benzalchloride  Benzotrichloride
 ‫א‬ K٢
ortho EOF‫א‬‫א‬‫א‬ K‫א‬‫א‬
‫א‬  meta EmF ‫א‬ ‫א‬    ‫א‬ ‫א‬ 
 ‫א‬   Kpara Ep F ‫א‬ ‫א‬   ‫א‬
 Benzene.‫א‬  K‫א‬‫א‬
W‫א‬‫א‬،‫א‬‫א‬،‫א‬
F
CI CH2CH3
CI

    CI
I
 
 O-dichlorobenzene m-chloroethylbenzene p-fluoroiodobenzene

- ٤٦ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH 3 COOH OH
CI

  NO 2  
 Br
m-nitrotoluene m-bromobenzoic acid o-chlorophenol

 W‫א‬‫א‬CH3-
CH3 CH3 CH 3
CH3

    CH3   CH 3
 o-xylene  m-xylene  p-xylene
 ‫א‬‫א‬
CI NO2
2
1
CI 1 CI 6 2
3
5 3
6 4 CI
F
  5   4

   
 1,2,3-trichlorobenzene  3-chloro-5-fluronitrobenzene
  ‫א‬F
 (1,2,6-trichlorobenzene)  E١‫א‬
   
OH CH3
1
Br Br NO2 NO2
6 2
5 3
4
  Br   NO2
   
2,4,6-tribromophenol 2,4,6-trinitrotoluene (TNT)
‫א‬) ‫א‬F
E١‫א‬  E١‫א‬
- ٤٧ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬٦ J٣
،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬K
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬

  ‫א‬‫א‬‫א‬‫א‬‫א‬

 ‫א‬،
 K‫א‬
_
Al2O3 CrO3 / 500ْ C
CH3

CH3(CH2)5CH3 + 3H2
Pt / 400ْ C

 Toluene K
CH3 Al2O3 _ Pt
+ 3H2
ْ
550 C

 Benzene

 

 

 W‫א‬‫א‬٧ J٣
‫א‬‫א‬‫א‬،‫א‬‫א‬ 
K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 WHalogenation‫א‬ K
‫א‬،
 ‫א‬ 
‫א‬‫א‬،‫א‬‫א‬E‫א‬‫א‬‫א‬F‫א‬
،E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬،
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
CH2Cl CHCl2 CCl3

Cl2 Cl2 Cl2

CH3 ‫ﺿﻮء‬ ‫ﺿﻮء‬ ‫ﺿﻮء‬

Benzoyl Benzoal Benzotrichloride

chloride chloride
CH3 CH3

Cl 2/FeCl 3
Cl
Toluene
+

  o-chlorotoluene p-chlorotoluene

 W‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 ‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
  ‫א‬‫א‬‫א‬
 ‫א‬
 K
 

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

CH3 COOH
KMnO4 or
K2Cr2O7

  Benzoic acid
CH2CH2CH3 COOH
CH3 COOH
KMnO4 or
+ (CO2 + H2O)
K2Cr2O7

Phthalic acid
  ( 1,2- benzenedicarboxylic acid)

W‫א‬ .١
W‫א‬ -‫أ‬
،‫א‬‫א‬‫א‬
EthylbenzeneK‫א‬،‫א‬‫א‬‫א‬
 KCyclohexane 
CH 2CH 3 CH 2CH 3
Ni,Pt or Pd
+ 3H 2

 Ethylbenzene Ethylcyclohexane

 W‫א‬‫א‬‫א‬‫א‬ J
‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬ 
، ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬ ، ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
، ‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
Alkylation E‫א‬–F  J١

CH3
AlCl3
+ CH3Cl + HCl
 
 
AcylationE‫א‬–F  J٢

O
O C _ CH3
CH _ C _ Cl AlCl3
+ 3
 
 
Halogenation‫א‬  J٣
 
Br
FeBr3
+ Br2
 

Nitroation‫א‬  J٤

NO2
H2SO4(conc.)
+ HNO3
 
‫א‬  J٥
SO3H Sulfonation
SO3
+ H2SO4 
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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬‫א‬٨ J٣
، ‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
Anisole K‫א‬‫א‬،‫א‬
Knitroanizole ‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
OCH3 OCH3 OCH3
HNO3 NO2
H2SO4 +

  NO2
‫א‬‫א‬ 
‫א‬‫א‬–‫א‬
 K‫א‬
NO2 NO2
HNO 3
H2SO4
  NO2

=O،R+F‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬ ‫א‬EH+،Br+،NO2+،CH3C+
‫א‬‫א‬‫א‬‫א‬،‫א‬

 ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬
 ‫א‬–‫א‬ .١
 W‫א‬‫א‬‫א‬‫א‬
 -NH2(-NHR,-NR2) ,-OH >-OR,-NHCOCH3 > -C6H5 ,-R
 K‫א‬ERF
K‫א‬‫א‬–‫א‬ .٢

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 E-F,-Cl, - Br)

W‫א‬‫א‬K‫א‬ .٣
 K-NO2, -N+(R)3,-C=N,COOH( -COOR ),-SO3H,-CHO,-COR

 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬،‫א‬ 
 K‫א‬‫א‬‫א‬
NO2 NO2
HNO3 Br2,Fe
H2SO4
Br
m-bromonitobenzene
Br Br Br
NO2
Br2,Fe HNO3
+
H2SO4

NO2
o-bromonitro p-bromonitro
  benzene (38%) benzene (62%)

 W‫א‬‫א‬‫א‬٩ J٣
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬K‫א‬
‫א‬K‫א‬،‫א‬‫א‬،EF
‫א‬‫א‬KE‫א‬F‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬،
K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

- ٥٣ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
 W‫א‬‫א‬‫א‬W١
 

CH = CH 2 COOH CH3
Br NO2
a) b) c)
CH3

CH3 COOH
CI
d) e)
I I NO 2

 
 W‫א‬‫א‬‫א‬‫א‬‫א‬W٢
a) 1,3,5-trichloro benzen b) m-bromotoluene
c) p-bromonitro benzene d) lsopropyl benzene
e) 4-bromo-2,3-dinitrotoluene f) m-chloro benzoic acid

 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W٣
 
CH(CH 3)2
-
KMnO 4 / OH

 
CH 3
Br 2 /hv

- ٥٤ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

NO 2
Br 2
FeBr 3
OC 2H5
AICI 3
+ CH 3CH 2CI

CI
O
AICI 3
+ CH 3 C - CI

CH 3
H 2O 3
HNO 3

AICI 3
+ CH 3 CHCI CH 3

CN
Br 2
FeBr 3

 
 
 
 
 
 
 
 
 

- ٥٥ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 ٣ J٨
 W١
O-Bromostyrene  J‫א‬
3,5- Diiodo toluene J

 
 W٢
CH3

 Br 
CH (CH 3)2

 
 W٣
CH(CH 3)2 COOH
-
KMnO 4/OH


NO 2 NO2
Br 2
FeBr 3
 Br 
CH3 CH3 CH3
NO2
HNO 3
+
H2SO4

 NO2
CH (CH 3) 2
AICI 3
+ CH 3 CHCI CH 3

 

- ٥٦ -
 ‫א‬‫א‬
‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬

٤
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣

 W‫א‬‫א‬‫א‬
 K٪٨٠‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K

 W‫א‬‫א‬
 KOverhead Projector .١
K‫א‬‫א‬ .٢
K .٣

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

- ٥٧ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W١ J٤
،  ‫א‬‫א‬‫א‬‫א‬ 
R،R - X‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،X،
 K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬

 W‫א‬‫א‬‫א‬٢ J٤
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬
‫א‬F‫א‬Alkyl‫א‬‫א‬‫א‬
‫א‬‫א‬EF‫א‬IUPAC‫א‬‫א‬،E
 W‫א‬‫א‬
 
CH3Cl CH3CH2CH2Br
1˚ halides
 (Methyl chloride) (n – propyl bromide)
‫א‬
 Chloromethane 1 - Bromopropane

 
CI
I
CH3 - CH - CH3 2ºhalides
EIsopropyl iodide) ‫א‬
(Cyclopentyl chloride)
2- Iodopropane
Chlorocyclopentane
CH3 CH3
CH3 - CH2 - CH2 - C - CH = CH2 CH3 - C - CH3 3º halides
‫א‬
Br Br
3-Bromo-3-methyl-1-hexene (tert-Butyl bromide)
 W‫א‬‫א‬‫א‬‫א‬
- ٥٨ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

_ CH2 = CH
CH2 = CH CH2
CH2X
X X
Allylhalide Vinylhalide Benzylhalide
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 
CCl4 CHCl3 CH2Cl2
(Carbontetrachloride) (Chloroform) (Methylene chloride)
Tetrachloromethane Trichloromethane Dichloromethane

Br
CHBr3 CHI3
CH3 - C - CH2CH3

(Bromoform) (Iodoform) Br
2,2-Dibromobutane

 W‫א‬‫א‬‫א‬٣ J٤
‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬F‫א‬‫א‬‫א‬K‫א‬
 K‫א‬E‫א‬

 W‫א‬‫א‬‫א‬٤ J٤
‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬ 
 W

- ٥٩ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫ א‬.١
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬

Cl2
CH3CH3 CH3CH2CI + HCI + ...
UV or heat
‫ﺿﻮ او ﺣﺮارة‬

Br2
CH3 - CH = CH2 CH2 - CH = CH2 + HBr
UV or
Br

 ‫א‬‫א‬‫א‬‫א‬ .٢
‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬ 
 W‫א‬‫א‬
HCl
CH3 - CH = CH2 CH3 - CH - CH3
CCl4
Cl
‫א‬‫א‬
 W‫א‬‫א‬
HBr
CH3-CH = CH2 R-O-O-R CH3CH2CH2
Br
 

‫א‬
 
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W
HCl HCl
CH CH CH2 = CH CH3CHCl2
CCl4 CCl4
Cl

- ٦٠ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F‫א‬‫א‬‫א‬‫ א‬.٣
‫א‬HX‫א‬‫א‬‫א‬ ‫א‬‫א‬ 
 W‫א‬EPCl5 , PCl3 , PBr3F‫א‬‫א‬SOCl2‫א‬

 
HCl
CH3(CH2)5 CH2OH CH3(CH2)5 CH2 +H2O
ZnCl2 / 150ْ
Cl
NR3
CH3CH2OH + SOCl 2 CH3CH2Cl + SO 2 + HCl

CH3CH2OH +PBr3 CH3CH2Br + P (OH)3

 

 W‫א‬‫א‬٥ J٤
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬KE‫א‬F‫א‬‫א‬
KE‫א‬F‫א‬
 KKKK‫א‬‫א‬

 Nucleophilic substitution reactions‫א‬‫א‬‫א‬ K١

 ‫א‬‫א‬‫א‬‫א‬ 
E‫א‬‫א‬‫א‬F‫א‬‫א‬
‫א‬‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

R3Cδ+χδ- R3C-Nu + χ –

 W‫א‬‫א‬‫א‬‫א‬

- ٦١ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

O
- - - -
SR , SH , CH3NH2 , NH3 , - O - C - R , OR ,OH
.. - -
N (CH3) 3 , HN (CH3)2 , CN ,R - C = C
 
‫א‬،‫א‬‫א‬ ‫א‬‫א‬ 
 W‫א‬‫א‬
 
KOH
CH3CH2CH2Br CH3CH2CH2OH
H2O

Elemination reactionsEEFE‫א‬‫א‬F‫א‬ K٢

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬

- +
_ KOH (Or) CH3CH2O Na
CH3CH CH3 CH3 - CH = CH2
EtOH /
Br

-4‫א‬‫א‬ K٣
Grignard formation K

 K‫א‬‫א‬‫א‬‫א‬‫א‬

ether
CH3CH2CH2Br + Mg CH3CH2CH2MgBr

 ‫א‬ ‫א‬           
 K،‫א‬‫א‬‫א‬‫א‬‫א‬
 
- ٦٢ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 ‫א‬ K
W‫א‬‫א‬

- +
CH3CH2CH 2Br + 2Li CH3CH 2CH2 Li + LiBr

 K‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬‫א‬٦ J٤
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 KD.D.T.‫א‬
H

Cl C Cl
CCl 3

  D.D.T
 
‫א‬‫א‬‫א‬–[CF2–CF2]nTeflonW‫א‬ 
‫א‬–[H2–CCl2]n–‫א‬‫א‬‫א‬‫א‬‫א‬
K ‫א‬‫א‬‫א‬‫א‬–[CH2 – CHCl2-]n–PVC K‫א‬
CCl3FCCl2F2‫א‬CF3CHClBr‫א‬HCX3haloform‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬
 Antifungus‫א‬Antibiotics‫א‬‫א‬‫א‬
 

- ٦٣ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 
 EIUPAC F‫א‬‫א‬‫א‬‫א‬W١
 
Br
CH3CH_ CH _ CH3
E E
  Br CH3
 
NO2

_ _ _
CH CH3  E CH 3 CH2 CH=CH 2 E
Cl  Cl
 
   

CH2 = CH CH2Cl E
 
 E3◦ 2◦1◦F‫א‬‫א‬‫א‬W٢
 
Br
CH3 Cl CH3
CH3 C CH3 E E E
 Cl   
 
 K‫א‬‫א‬‫א‬‫א‬W٣
 
CH3
HCl E
CH3CHOH ZnCl
 2

HBr
CH 3 E

CH3
Br2 E
CH3CHCH3 hv
Cl2
CH2CH3 hv 

SOCl2
OH E

- ٦٤ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

+ -
_ CH Na O CH2CH3
CH3CH2CH 3 CH3CH2OH E
 Br
Br
KOH
CH3 C CH2
EtOH

CH3
NH2CH3  E
CH 3CH 2CH 2Cl
- +
CH3C C Na
CH 2CH 2Br E

KOH
CH 3CH _ CH 3 E
EtOH /
Br
ether E
CH 3CH 2CH 2Br + Mg
 
 W‫א‬‫א‬‫א‬‫א‬W٤
 
-
OH  E١
CH 3CHBrCH 3 ethanol
-
OH  E٢
CH 3CHBrCH 3 H2O
-
CN  E٣
(CH 3)3CBr
ethanol
H 2O  E٤
(CH 3)3CBr
 
 
 
 
 
 
 
 
 
 
 
 

- ٦٥ -
  ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 ‫א‬
 

 W١
2-Bromo-3-methyl butane – ‫أ‬
1-Bromo-2-Nitro cyclohexane -‫ب‬
1-chloro-1-butene - ‫ﺟـ‬
 
 W٢

3◦ E 2◦ E  1◦ E

 

 W٣
CH3 CH3
HCl
CH3CHCl + H2O
E
CH3CHOH ZnCl2

CH3 CH3
Br2
CH3CHCH3 hv CH3 C CH3 E
Br
NH2CH3  E
CH 3CH2CH 2Cl CH3CH 2CH2NHCH 3
KOH
CH CH_ CH
3 3 EtOH / CH 3CH=CH 2 + HBr E
Br
 

 W٤
‫א‬‫א‬ J١
‫א‬‫א‬ J٢
‫א‬‫א‬ J٤
 
 

- ٦٦ -
 ‫א‬‫א‬
‫א‬ ‫א‬
‫א‬‫א‬

٥
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
 
 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 K
 
 W‫א‬‫א‬
 KOverhead Projector .١
 K‫א‬‫א‬‫א‬ .٢
K .٣
 
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

- ٦٧ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W١ J٥
 JOH‫א‬‫א‬ 
‫א‬‫א‬‫א‬،ArOH‫א‬‫א‬،ROH‫א‬‫א‬‫א‬
 ‫א‬R ،ArR‫א‬‫א‬
 Ar 
،SP3‫א‬‫א‬ ‫א‬،
KSP2‫א‬‫א‬
‫א‬‫א‬‫א‬، ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬
‫א‬K‫א‬‫א‬
 K‫א‬

 W‫א‬٢ J٥
‫א‬
 ‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 
  
Tertiary 3O Secondary 2O Primary 1O

R H H

R C OH R C OH R C OH

R R H

 ‫א‬ ‫א‬   ‫א‬ ‫א‬   ‫א‬ ‫א‬ 
   JOH    JOH    JOH 
 ‫א‬       
     K‫א‬ KR‫א‬
K‫א‬

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 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬٣ J٥
‫א‬KIUPAC‫א‬‫א‬‫א‬‫א‬،
 K‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫ א‬K١
 W‫א‬‫א‬‫א‬‫א‬
 
 CH3 OH  CH3CH2OH CH2=CH-CH2OH
 Methyl alcohl  Ethyl alcohol Allyl alcohol

CH3
CH3 CH CH3
CH3 c CH3
OH
OH

Isopropyl alcohol Tert-Butyl alcohol

OH CH2OH

Cyclopentyl alcohol Benzyl alcohol

 WE‫א‬FW‫א‬‫ א‬K٢
 JOH‫א‬‫א‬ K١
EeF‫א‬‫א‬‫א‬‫א‬ ‫א‬
CH3OHCH3CH2OH WK Jol
 MethanolEthanol
 

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 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

-OH‫א‬‫א‬‫א‬‫א‬ K٢
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬E١F‫א‬‫א‬‫א‬
CH3CH2CH2CH CH3
CH3CH2CH2OH
OH
1-Propanol 2-Pentanol
C2H5
OH
CH3CH2CHCH2CHCH3

OH

Cyclohexanol 4-Ethyl-2-hexanol
CH2CH2Br

CH3CH2CH2CHCH2 OH

2-(2-Bromoethyl)-1-Pentanol
 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
CH2CH3
CH2 CH CH CH CH3
CH3CH C CH2
OH CH3
OH

4-Methyl-1-Penten-3-ol 3-Ethyl-3-buten-2-ol
OH
CH C CH CH3

OH
CH3

3-Butyn-2-ol 4-Methyl-2-cyclohexenol

- ٧٠ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 -ol  ‫א‬tetra,tri ,di‫א‬‫א‬‫א‬ K٤

 KK‫א‬
 
 
CH2 CH2 CH2 CH CH2

OH
  OH OH OH OH

 1,2-Ethanediol 1,2,3-Propantriol

 Ethylene glycol Glycerol or Glycerene
 W‫א‬
   ‫א‬  ‫א‬     ‫א‬    
،     ‫א‬  -OH   
  ، 
،‫א‬‫א‬‫א‬
 W‫א‬‫א‬
OH OH
OH

Br NH2

Phenol m-Bromophenol p-Aminophenol

OH
OH

COOH

OH

o-Hydroxybenzoic
acid ( Salicylic Hydroquinone
acid)

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 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬‫א‬‫א‬٤ J٥
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬ ‫א‬  ‫א‬ ‫א‬     ‫א‬   
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
 K‫א‬‫א‬،EF‫א‬‫א‬
R Ar
Ar
O O
O O
H
R H H
H

 
 ‫א‬
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
Ethanol Propane
 L٤٦  °٧٨ ‫א‬‫א‬
L٤٤  °٤٢ ‫א‬
،‫א‬ ‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬
H R
o o o
R H
H H

 
 ‫א‬

- ٧٢ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬٥ J٥
 W‫א‬ K
،‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
OH
CH3CH = CH2 + H2O H+
CH3 CH CH3
Propene  2-Propanol
‫א‬،Ethanol ‫א‬Methanol ‫א‬‫א‬
 W

  water gas‫א‬‫א‬‫א‬‫א‬W‫א‬ K

 KE‫א‬‫א‬F
O
1300 C
C +H2O CO + H2

‫א‬‫א‬Water gas
 K300 atm300c ‫א‬‫א‬
Zn + Cr 2 O3 as Cat.
CO + H 2 + H2 CH3OH
Water gas

 WNatural gas‫א‬‫א‬ K

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K900 Co
Ni as Cat.
CH4 + H2O CO + 3H 2O
 K‫א‬‫א‬‫א‬Synthesis‫א‬‫א‬‫א‬
ZnO + Cr 2 O3 as Cat.
CO + H 2O O CH3OH
300C , 300 atm.

 

- ٧٣ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
        ‫א‬  K
: Ethyl hydrogen sulphate٨٠Co‫א‬
CH2 CH2 + H2SO4 CH3 CH2 O SO2 OH

 K‫א‬
CH3 CH2 O SO2 OH + H2O CH3 CH2 OH + H2SO4

 ‫א‬ ‫א‬ ‫א‬   ‫א‬ ‫א‬  K
Phosphoric F‫א‬‫א‬
Co‫א‬E‫א‬‫א‬acid on silca
 K70 atm٣٠٠
 W‫א‬ K
‫א‬‫א‬‫א‬ ‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬
SO3H - + OH
ONa

NaOH
HCl

Benzene sulfonic acid Sodium phenoxide Phenol

 W‫א‬‫א‬
،Propene ‫א‬‫א‬‫א‬‫א‬ ،Cumene‫א‬ E١
AlCl3‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 K‫א‬‫א‬
CH CH3

+ CH3 CH CH2
CH3

Cumene
- ٧٤ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

‫א‬‫א‬Hydroperoxide ‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬
CH3
OH

CH CH3 C CH3 +
H
+ O2 + ( CH3 )2 C O
CH3 O OH
Phenol Acetone

 
 K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬ E٢
- +
Cl O Na
Cl2 + OH
NaOH
H
o o
40 C 330 C

Benzene Chlorobezene Sodium phenoxide Phenol

 W‫א‬‫א‬٦ J٥
 W‫א‬‫א‬

 W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬-١
‫א‬ ،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،‫א‬
H2SO4
2CH3CH2OH O
(CH3CH2) 2 + H2O
140 C

Ethanol Diethyl ether

H2SO4
CH3CH2OH O
CH2 CH2 + H2O
180 C

 Ethylene

 K‫א‬‫א‬‫א‬‫א‬‫א‬
 WOxidation‫א‬
،‫א‬‫א‬‫א‬E1F‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬،‫א‬

- ٧٥ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

Cu/
CH3CH2OH CrO3 or Pyridine
CH3CHO
O
Ethanol (1) Acetaldehyde
3+
H2Cr2O7
CH3CH2OH CH3COOH + Cr
Acetic acid
OH O

H2Cr2O7
CH3CHCH3 CH3 C CH3
or Cu /
o
Alcohol ( 2 ) Ketone

OH  
Oxid Agent
CH3 C CH3

CH3
 

W‫א‬‫ א‬-٢
‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬
 K‫א‬
- +
CH3 OH + Na CH3 O Na + 12 H2
Methanol Sodium Methoxide

- +
OH O Na

+ Na + 12 H2

Phenol

- ٧٦ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬ -٣
K‫א‬‫א‬ ‫א‬‫א‬ ‫א‬‫א‬
 K‫א‬H+‫א‬
O
+
H
(Ar)R OH + RCOOH (Ar)RO C R + H2O
Alcohol or Phenol Ester
+
H
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
Acetic acid Ethyl alcohol Ethyl acetate

 

- ٧٧ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 WE3FE2FE1F‫א‬‫א‬‫א‬‫א‬ E١
CH3 CH2 CH2 OH CH2CH3 (A
(B
CH3 CH2 C OH

CH2CH3

Br (D CH3 (C

CH3 CH CH2 H2C C CH2 OH


OH
 W‫א‬‫א‬ E٢
(A (B OH (c (D
OH OH
CH2OH CH3 CH 3

Br OH 
NH2 CH3
   OH

 W‫א‬‫א‬ E٣
(A

CH3 CH CH2CH3 CH3 C CH2CH3

OH O
 
(B
O
+
H
CH3 CH2 C OH + CH3OH
 
CH CH CH OH
Cu , ? (C
  3 2 2
K2Cr2O7 H2SO4 ? (D
OH +

OH

(E

 
- ٧٨ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬‫א‬‫א‬ E٤
1) 2,4-Dimethyl-2-Octanol.
2) Cyclopentane-1,4-diol.

3) 2,2,2-Trichloroethanol.

4) 2-Butene-1,4-diol.

5) 3-Bromo-2-nonanol.

6) O- Bromophenol.

7) 2,4,6-Trichlorophenol

8) p-Hydroxybenzyl alcohol.

 
 
 
 
 
 
 
 
 
 

- ٧٩ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 WE1F‫א‬‫א‬
 K3o،  1,1-Diethyl propanol EA
.2o، 1-Bromo-2-propanol (D
 WE2F‫א‬‫א‬
 4-Amino-5-bromo phenol EA
2,4,6-Trimethyl phenol EC
 WE3F‫א‬‫א‬
KMnO 4 (A
H2O

O
(B
CH3 CH2 C O CH 3

O
CH3 CH2 C H (C

 WE4F‫א‬‫א‬
CH3
CH3-CH2-CH2-CH2-C-CH2-CH-CH3 (1
CH3 OH


CCl3-CH2-OH (3
CH3-CH2-CH2-CH2-CH2-CH2-CH-CH-CH3 (5
Br OH
 
OH
Cl Cl (7

Cl

 

- ٨٠ -
 ‫א‬‫א‬
‫א‬‫א‬
‫א‬‫א‬

٦
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬‫א‬ .٢
 
 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 K
 
 W‫א‬‫א‬
 KOverhead Projector .١
K .٢
 
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
 

- ٨١ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W١ J٦
 R/RR-O-R/‫א‬‫א‬‫א‬‫א‬ 
 WK
‫א‬‫א‬‫א‬،R/R‫א‬‫א‬
 K‫א‬
 W‫א‬‫א‬٢ J٦
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 ‫א‬ ‫א‬،Ether
 ‫א‬
 K‫א‬
CH3OCH2CH3 CH3CH2OCH2CH3 CH3OCH3
Ethyl ether Methyl ether
Ethyl methyl ether

o CH3 o
Methyl phenyl ether Phenyl ether
( Anizole )
-O-R،
 IUPAC ‫א‬‫א‬‫א‬‫א‬ 
‫א‬، ‫א‬REAlkoxy)‫א‬
 W‫א‬‫א‬R(Aryloxy)
CH3CH2CHCH3
Br o CH2CH3
p-Bromophenoxy ethane
oCH3
2-Methoxy butane

o CH2 CH3

  Ethoxy cyclohexane
‫א‬‫א‬‫א‬oxa‫א‬ 
 W‫א‬‫א‬‫א‬‫א‬ K‫א‬

- ٨٢ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

1 2 3 4 5 6 7 8 9
CH2 O CH2 CH2 O CH2 CH2 O CH3

Cl

1-Chloro-2,5,8 -trioxanonane
 
 W‫א‬‫א‬

o o O
Oxlane Oxane 1,4-Di oxane
or or or
Tetrahydrofuran Tetrahydropyran 1,4-Dioxa cyclohexane
( THF )

o
o
CH2 CH2
Oxetane
Oxiran e cepoxide
or
or Trimethylene oxide
Ethylene oxide
 
 W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
 ، ‫א‬‫א‬ 
K
 ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
K ‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬ 
‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

- ٨٣ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

R
O H
O R
R
H O

R
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

‫א‬ ‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬

 o78 46 Ethanol CH3CH2OH

   o24 J 46 Methylether CH3OCH3

  o42 J 44 Propane CH3CH2CH3

 W‫א‬‫א‬‫א‬٣ J٦
‫א‬‫א‬F‫א‬‫א‬‫א‬ 
، ‫א‬‫א‬‫א‬ E‫א‬‫א‬‫א‬
 K
‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬EPeroxide)‫א‬(‫א‬‫א‬‫א‬F
 K
‫א‬‫א‬‫א‬‫א‬ 
،Fe+++‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬FeSO4
 W‫א‬‫א‬‫א‬‫א‬

- ٨٤ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 
-
+++ SCN
Peroxide + Fe Fe(SCN)3
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬F‫א‬‫א‬ .١
 KE‫א‬‫א‬
K‫א‬‫א‬‫ א‬.٢
K ‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
 W‫א‬‫א‬٤ J٦

 W‫א‬‫א‬‫א‬W 
‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬‫ א‬.١
‫א‬‫א‬‫א‬K ‫א‬‫א‬
 K‫א‬‫א‬
H2SO4
CH3CH2OH CH3CH2OCH2CH3
140
 W .٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  
F‫א‬‫א‬،Ealkoxide ion‫א‬F‫א‬
 K‫א‬‫א‬‫א‬Ephenoxide ion‫א‬
- +
CH3 CH O Na + CH3CH2Br CH3 CH O CH2CH3

CH3 CH3

 Ethyl isopropyl ether

- ٨٥ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

- +
O Na O CH3

+ CH3Br

Anizole
 W‫א‬‫א‬‫א‬W

W‫א‬‫א‬‫א‬‫ א‬.١
 K‫א‬‫א‬‫א‬‫א‬

W‫א‬Diethyl ether .٢
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬‫א‬٥ J٦
، ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬
+
H
CH 3 CH 2 O CH 2 CH 3 + 2HI 2CH3 CH 2-I + H 2O

  Iodoethane
 
 
 
 
 
 
 

- ٨٦ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F

 W‫א‬‫א‬ .١
C6H5CH2 O C3H7 CH3CH2CH2OCH2CH3E1
E4
CH3 CH CH2 CH CH3 (5 (CH3CH2CH2CH2)2OE2

CH3 O CH2CH3

CH3 O CH CH3 (3
(6

CH3
O CH2 CH3 

 W‫א‬‫א‬‫א‬‫ א‬.٢
1) Diisopropyl ether. 2) Diallyl ether.
3) tert-Butyl methyl ether. 4) Benzyl ether.
5) Phenyl ether. 6) 4-Ethoxy -2-Methylhexane.

 W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
CH3

(1) + (2) CH3 C O CH2 (1

CH3

O-
CH3O + (CH3)3CBr (3) (2
 
-
O
(CH3)C O + CH3I (4) (3
 
 
HI acid conc.
(CH 3)2CHCH 2OC(CH 3)3 (5) (4
with


- ٨٧ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 K‫א؟‬‫א‬‫א‬ .٤
CH3CH2CHCH2CH2CH3 (2   CH3CH2CH2CH2CH2CH2CH3 (1
 OH
  CH3CH2CH2 O CH2CH2CH3 (3

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

- ٨٨ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
WE1F‫א‬‫א‬
Dibutyl ether (3 Ethyl propyl ether (1
Isopropyl methyl ether (5
 WE2F‫א‬‫א‬
CH 3 O C (CH 3)3 (2 (CH 3)2 CH O CH (CH 3)2 (1
CH3-CH-CH 2-CH 2-CH-CH 3 (6
CH3 O C2H5
 WE3F‫א‬‫א‬
(CH3)3 C O CH 3 (2
(CH3)3 C O CH 3 (3
 
 

- ٨٩ -
 ‫א‬‫א‬
 ‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬

٧
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫ א‬.٢
 K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣

 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 K

 W‫א‬‫א‬
 Overhead Projector. .١
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٢

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
 
 
 
 

- ٩٠ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W١ J٧
‫א‬K   C=O ‫א‬‫א‬‫א‬‫א‬
O

EArF،R R(Ar)-C-H W

  ‫א‬‫א‬
O

 R , R  R
C R
W‫א‬‫א‬‫א‬K
 K
 W‫א‬‫א‬‫א‬٢ J٧
 KIUPAC‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

 W‫א‬‫א‬

 W‫א‬‫א‬ J 
 Jic acid‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬
‫א‬‫א‬aldehydeE‫א‬‫א‬‫א‬F
 K‫א‬
 
O
 ‫א‬‫א‬ Formic acid
H C H
  Formaldehyde
O

 ‫א‬‫א‬
CH 3 C H  Acetic acid
  Acetaldehyde
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
(C C C C O)
 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 W‫א‬‫א‬

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

CH2CH3 O

CH3 CH CH C H
B

CH3
 
α,β -Dimethyl Valeraldehyde

 W‫א‬ J 

F‫א‬‫א‬‫א‬‫א‬‫א‬ 
 Wketone‫א‬E‫א‬‫א‬
O O

CH3 C CH3 CH3 C CH( CH3)2

Dimethyl ketone Methyl isopropyl ketone
 
  ( acetone )
Phenyl ‫א‬‫א‬‫א‬phenone‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬E-oic acid F-ic acid
O O

C CH3 C

  Acetophenone  Benzophenone

 W‫א‬‫א‬

 W‫א‬‫א‬ J 
، ‫א‬‫א‬  Jal‫א‬‫א‬‫א‬ Je ‫א‬‫א‬‫א‬
–KK ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 W‫א‬‫א‬

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

O CH3 O
CH3 C H
CH3 CH CH2 C H
  Ethanal
 3-Methyl butanal
‫א‬ ‫א‬‫א‬ 
 K‫א‬
O O

C H
C H

  Benzaldehyde CH 3

 p-tolualdehyde

 W‫א‬–
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬ Je‫א‬E Jal F Jone ‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬
 K‫א‬‫א‬
O O O

CH3 C CH3 CH2 CH C CH3

 Propanone 3-buten-2-one
 Cyclopentanone 
 W‫א‬‫א‬‫א‬‫א‬‫א‬٣ J٧
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
+ -
‫א‬ 
 ‫א‬‫א‬‫א‬‫א‬ C=O

‫א‬ ‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

- ٩٣ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
 K‫א‬
O
C O H H

 
 ‫א‬ 
 W‫א‬‫א‬‫א‬‫א‬‫א‬
Formalin‫א‬،‫א‬‫א‬‫א‬‫א‬ 
‫א‬K‫א‬‫א‬،E٪37F
، ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬، ‫א‬‫א‬،56
 K‫א‬‫א‬
 W‫א‬‫א‬‫א‬٤ J٧
 W‫א‬‫א‬‫א‬‫א‬–
 W‫א‬ K
، ‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬K‫א‬
O
Cu /
CH3CH2CH2OH CH3CH2C H
o
1-Propanol (1) Propanal
 
OH O
+3
H2Cr 2O7
CH3CHCH 3 CH3C CH3 + Cr
o
2-Propanol (2) Acetone
 
 
 
- ٩٤ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬E
 
 ‫א‬F‫א‬
 W‫א‬‫א‬‫א‬
O O
AlCl3
+ CH3CH2C Cl C CH2CH3 + HCl

  Ethyl phenyl ketone

 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬‫א‬‫א‬ J 

 W‫א‬‫א‬‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
O (1
CuO-Ag
2CH 3OH + O2 O 2H C H + 2H 2O
  500-650 C

O
(2
PdCl2
CH2 CH2 + 1/2 O2 CH3 C H
H2O
 
 W‫א‬‫א‬ K٢
 K‫א‬500 CO‫א‬‫א‬2-propanol‫א‬‫א‬
O
Cu as Cat.
(CH3)2CHOH O
CH3 C CH3
500 C
2-Propanol Acetone
 
 W‫א‬‫א‬‫א‬٥ J٧
،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬ ‫א‬‫א‬K‫א‬ 

- ٩٥ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

‫א‬EF‫א‬ ،‫א‬
 W‫א‬‫א‬‫א‬‫א‬

 (Cyanohydrine )KHCN‫א‬ .١
O OH
-
CN
CH3 C H + HCN CH3 C H

CN
  Acetaldehyde cyanohydrine

O
- OH
CN
CH3 C CH3 + HCN CH3 C CH3
CN
Acetone cyanohydrine
 

 W‫א‬‫ א‬.٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WG-NH2
O
  
C NH 2   NH Ar H = G OH
  NH

‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
F ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬E‫א‬
O
+ CH 3
H
CH 3 C CH 3 + NHNH 2 C N NH
CH 3

  Acetone Phenylhydrazene

- ٩٦ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 WReduction‫א‬‫ א‬.٣
‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ 
 KNaBH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
OH
O H2/Pt
CH 3 CH CH 3
CH3 C CH 3
1)NaBH 4
CH 3 CH CH 3
2)H 2 O
OH

  2-Propanol

 WOxidation‫ א‬.٤
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
O O
(O)
R C H R C OH
 
 
   
 
 
 
 
 

- ٩٧ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 W‫א‬‫א‬ .١
O O
Cl
(2 CH 3CH 2C H (1
 
 
O O

C H (4 (CH 3)2CHCCH(CH 3)2 (3


 
  O

CH 3CH 2CH 2CCH 3 (5

 
 

 W‫א‬‫א‬‫א‬‫ א‬.٢
 
 Acetophenone (2 Benzaldehyde (1
Benzylphenyl ketone (4 Benzophenone (3
3-Pentanone (6 Butanal (5
 W‫א‬‫א‬ .٣
 

O O
? (1
C Cl + C


O

CH 3 CH 2 CH 2 C H
1) NaBH 4
+ ? (2
 2) H3O

O
1) NaBH 4
+
? (3
2) H3O

O


CH 3 C CH 3
NH 2 OH
? (4
O


CH 3 C H
Oxidation.
? (5
O
H 2 / Pt
? (6
 CH 3 CH 2 C H

- ٩٨ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 WE1F‫א‬‫א‬
. 2-Chlorocyclohexanone (2   . Propanol (1
   . Methyl propyl ketone (3
 WE2F‫א‬‫א‬‫א‬
O CHO
(1
CH3 CH2 CH2 C-H (4
  
  O
CH3 CH2 CH2 C-CH3 (6

 WE3F‫א‬‫א‬‫א‬
N-OH
(4  
CH3 CH2 CH2 CH2 OH (2
CH3 -C- CH3
 
  OH
CH3 CH2 C CH3 (6

 

 

- ٩٩ -
 ‫א‬‫א‬
 ‫א‬‫א‬
 ‫א‬‫א‬

٨
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫א‬ .٢
 
 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 K
 
 W‫א‬‫א‬
 Overhead Projector. .١
 K .٢

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
 
 

- ١٠٠ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 W١ J٨
E JCOOH) ‫א‬
 ‫א‬‫א‬ 
KE-OHF ‫א‬EC=OF‫א‬‫א‬K
، ‫א‬
 ‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬‫א‬٢ J٨
 W‫א‬‫א‬ J‫א‬
‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬ 
 KE8 J1FKW‫א‬‫א‬‫א‬‫א‬ K

 WE‫א‬‫א‬‫א‬E8 J1FF
 ‫א‬  ‫א‬  ‫א‬‫א‬
‫א‬،Formic  Formic acid
HCOOH
 K‫א‬  ‫א‬
Acetum
 Acetic acid
‫א‬،‫א‬‫א‬
 CH3COOH  
‫א‬‫א‬
 ‫א‬
 K‫א‬
،Butyrum Butyric acid
CH3(CH2)2COOH
K‫א‬‫א‬‫א‬  K‫א‬
 
β،α‫א‬‫א‬، ‫א‬‫א‬ 
‫א‬‫א‬α‫א‬‫א‬‫א‬‫א‬KKKγ،
 K‫א‬‫א‬‫א‬‫א‬‫א‬
 
 

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

‫א‬‫א‬ O
α γ β α
C C C C C C OH
‫א‬‫א‬ 5 4 3 2 1

 
 W
CH3 CH3

CH3 CH CH COOH
 2,3-Dimethylbutanoic acid 
  α،β -Dimethylbutyric acid 

 WIUPAC ‫א‬‫א‬W 

‫א‬‫א‬‫א‬e‫א‬oic acid ‫א‬ 
‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬
O Br

CH3 CH COOH
CH3 C OH
2-Bromopropanoic acid
Ethanoic acid
(Acetic acid)
COOH

CH3

CH3 C CHCOOH
Cyclohexane
3-Methyl-2-butenoic acid Carboxylic acid

 WW 

 W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.١

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

COOH OH CH3
COOH

  Benzoic acid   Salicylic acid COOH

 P-Toluic acid
 K

‫א‬‫א‬ .٢
 W
COOH
COOH COOH
COOH
CH2
COOH (CH2)4 COOH
CH2
CH2
COOH COOH
COOH
COOH

 Oxalic acid  Malonic acid  Succinic acid Adipic acid  Phthalic acid
‫א‬،Fatty acids‫א‬‫א‬ .٣
‫א‬،2612‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬
 
CH 3 (CH 2)14 COOH CH3 (CH 2)16 COOH

Palmitic acid Stearic acid

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬‫א‬‫א‬٣ J٨
،‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬‫א‬،‫א‬
 KO 00،L46Z‫א‬‫ א‬HCOOH Formic acid
 KO78،L46Z‫א‬‫א‬ C2H5OH Ethanol

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬
_ +
O H O
R C C R
+ _

  O H O
 E‫א‬‫א‬‫א‬F
 W‫א‬‫א‬٤ J٨
‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬
_
H2O +
HCl H3O + Cl
 
‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
_ +

 
RCOOH + H O
2 RCOO + H3O
‫א‬‫א‬‫א‬‫א‬‫א‬  
‫א‬‫א‬K‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬ ‫א‬
- ١٠٤ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

_
O O O
_
R C R C R C
_
O O O
 

 W‫א‬‫א‬‫א‬‫א‬‫א‬

 WElectron-withdrawing group‫א‬‫ א‬.١

 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
 W‫א‬
  ....., -COOH , -SO3H , -CN , -NO2 , Br , Cl ,F
Benzoic acid  p-Nitro Benzoic acid‫א‬
 KPara‫א‬‫א‬-NO2

  :Electron-donating group‫א‬‫ א‬.٢

،‫א‬‫א‬‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬
W
-OH , -NH2 , -OCH3 , -CH3
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬ JCH3‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬EInductetive effectF
‫א‬EpKaF‫א‬‫א‬‫א‬
 WEChlorobutyricF
Cl Cl Cl

CH3CH2CHCOOH CH 3CHCH 2COOH CH 2CH2CH 2COOH

CH 3CH 2CH 2COOH
 PKa = 4.82  PKa = 2.85  PKa = 4.05  PKa = 4.52

- ١٠٥ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

Z1  W92  W6    W2

 ‫א‬
 
‫א‬Ka‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬ pKa
_ + 
[ RCOO ] [ H ]
Ka = [ RCOOH ]

_ log Ka = pKa
 K‫א‬pKaKa‫א‬
‫ﺗﺰداد اﻟﺤﻤﻮﺿﺔ‬ Ka ‫زﻳﺎدة‬
‫ﺗﻘﻞ اﻟﺤﻤﻮﺿﺔ‬ pKa ‫زﻳﺎدة‬
 
 W‫א‬‫א‬‫א‬‫א‬
 ‫א‬  pKa  Ka  ‫א‬
 Ð Ð  3.74 1.77*10-4 Ð HCOOH
 Ð Ð 4.47 1.76*10-5 Ð CH3COOH
-5
 Ð Ð 4.85 1.43*10 Ð CH3CH2COOH
 W‫א‬‫א‬٥ J٨
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬،‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬ .١
O
H2Cr 2O7 +3
RCH 2 OH ( ‫) أﺧﻀ ﺮ اﻟﻠ ﻮن‬
 
OR R C H RCOOH + Cr

 W‫א‬ .٢
‫א‬‫א‬(Ar)R-CNK‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬

- ١٠٦ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

_
CN  
  R-X RCN

 K‫א‬‫א‬‫א‬

+
H3 O , +
RCN RCOOH + NH 4
 
 W‫א‬ .٣

 
R
KMnO4 ,
COOH

C2H5

KMnO4 ,

 Ethyl benzene Benzoic acid

 W‫א‬‫א‬٦ J٨
‫א‬
 K  ‫א‬‫א‬‫א‬
 K‫א‬‫א‬

 W‫א‬‫א‬‫א‬‫א‬‫ א‬.١
_
+
CH3COOH + NaOH CH3COO Na + H 2O
Acetic acid Sodium acetate
 
_ +
Ph COOH + NaOH Ph COO Na + H 2O

  Benzoic acid Sodium benzoate

،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬

- ١٠٧ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

_
+
(Ar) R COOH + NaHCO 3 (Ar) R COO Na + H 2O + CO2
 
 K‫א‬،‫א‬‫א‬‫א‬

 W،‫א‬‫א‬ .٢
RCON
‫א‬‫א‬
 RCOOR‫א‬‫א‬RCOCl‫א‬‫א‬
O  
R-C-O-C-R  ‫א‬
 W‫א‬‫א‬٧ J٨
E-OHF‫א‬‫א‬‫א‬‫א‬ 
‫א‬–NH2Cl-RCOO- JOR‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬  ‫א‬‫א‬
O O
‫א‬
 CH3 C Cl Acetyl chloride
R C X
O O
 
 CH3 C OC2H5 Ethyl acetate R C OR
O
O
C NH2 ‫א‬
NH2
Benzamide  R C
 
O O O O
‫א‬
CH3 C O C CH3 Acetanhydride R C O C R
O O _
_
+  ‫א‬ +
 CH3 C O Na Sodium acetate R C O M

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 ‫א‬‫א‬١ J٧ J٨

 :Acid halides ‫א‬‫א‬W 

،-yl halide‫א‬‫א‬‫א‬ - ic acid‫א‬
 W‫א‬‫א‬
O O
CH3 C OH CH3 C Cl

Acetic acid Acetyl chloride

 
 :Esters ‫א‬‫א‬W
 ‫א‬‫א‬،-ate‫א‬‫א‬‫א‬-ic acid‫א‬
‫א‬ 
 WKE‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬
O O
CH3 C OH CH3 C OC2H5

  Acetic acid Ethyl acetate

 WAmides‫א‬‫א‬W 
 WKamide‫א‬‫א‬‫א‬ JoicAcid‫א‬
O O
CH3 CH2 C OH CH3 CH2 C NH2

Propanoic acid Propanamide

 
 WAcid anhydrides‫א‬‫א‬W ‫א‬
 .Anhydrideacid‫א‬

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

O O O
C O OH C O C

Benzoic acid Benzoic anhydride

 
 :Acid salts‫א‬W 
‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬
O O _ +
CH3 C OH CH3 C O NH 4

Acetic acid Ammonium acetate

 

 W‫א‬‫א‬‫א‬‫א‬‫א‬٢ J٧ J٨
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬
K ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
_ O
O O
.. + C
R-C-NH2 R-C = NH 2 , .. +
R NH2
 
 ‫א‬‫א‬  ‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬٣ J٧ J٨
 K‫א‬
O
R C OR

SCO1 2
in Benzene

O O O O
ROH
R C O C R R C OH R C OR
H2SO4 H+
Acid anhydride Ester
Acid

NH 3 NaOH

O O
- +
R C OR R C O Na
Acid Acid salt
  Amide

 
 
 

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 W‫א‬‫א‬ K١
O CO 2H
2) OH
1) CH 3 CH CH C OH

OH NH 2

NH 2

O O
_ + OCH 3
3) CH 3 CH 2 CH 2 C O NH 4  4) CH 3 CH 2 C

O O O
CH 3
5) C O C CH 3 6) H C N
CH 3
 
O O
7) CH 3 CH 2 C Cl
 8)3 2 CH CH CH C
2 2 NH

 W‫א‬‫א‬‫א‬‫א‬‫ א‬K٢
a) 2,3-dibromopentanoic acid.
b) Methyl benzoate.
c) Methyl formamide.
d) m-nitrobenzoyl chloride.
e) Potassium formate.
f) N,N-diethylpropanamide.
g) Benzoic formic anhydride.
h) Ethyl 2-aminopropanoate.
 ‫؟‬‫א‬‫א‬‫א‬ K٣
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K 
 K‫א‬‫א‬ K

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  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬ K٤
+

1) CN
H2O / H
?

2) CH3 CH2H5
KMnO 4
?

O
3) CH3CH2 C OH
SOCl 2
?
 Benzene
O
4) CH3 C OH
H
+
?

O

5) 2CH3 C CH3 ?
H2SO4


 
 
 
 
 
 
 
 
 
 
 
 
 
- ١١٣ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 WE1F‫א‬‫א‬
2) 4-Amino-2-hydroxy benzoic acid.
4) Methyl propanoate.
5) Acetic benzoic anhydride.
7) Propanoyl chloride.
 WE2F‫א‬‫א‬
O
H-C-NHCH 3 (3 CH 3 -CH2-CH-CH-COOH (1
Br Br
O _ O O
+
H-C-O K (5
-C-O-C-H (7
 WE3F‫א‬‫א‬‫א‬

 ‫א‬‫א‬‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
O O
+ _
H-C-OH H + H-C-O
 
 ‫א‬‫א‬‫א‬
  
+
 KE H ‫א‬،‫א‬F
O O _
+
CH3-C-OH H + CH3-C-O " ‫" اﻟﻘﺎﻋﺪة اﻟﻤﺮاﻓﻘﺔ‬

  ‫א‬‫א‬CH3F 
?‫א‬?E 
 KEH+‫א‬F

- ١١٤ -
  ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬

‫א‬،‫א‬‫א‬ K٢
‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 WE4F‫א‬‫א‬‫א‬
O
HOOC COOH (2
CH3-C-O C 2H5 (4
 

- ١١٥ -
  

‫א‬‫א‬
‫א‬
‫א‬

٩
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬ .١
 K‫א‬‫א‬‫א‬ .٢
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
 
 W‫א‬‫א‬‫א‬
 K٪90‫א‬‫א‬‫א‬
 
 W‫א‬‫א‬
 K
 
 W‫א‬‫א‬
 KOverhead Projector  .١
K .٢
 
 W‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬

- ١١٦ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W١ J٨
EF‫א‬ ‫א‬ 
‫א‬KEFEF‫א‬
‫א‬‫א‬KEF‫א‬‫א‬‫א‬‫א‬
 K‫א‬RR3N , R2NH , RNH2‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 W‫א‬٢ J٨

 W‫א‬١ J٢ J٨
 W‫א‬‫א‬‫א‬
 3O 2O   1O
  ‫א‬ ‫א‬
‫ א‬‫ א‬ K‫א‬
K‫א‬ K
(C2H5)3N (CH3)2NH CH3NH2  
 Triethylamine  Dimethylamine  Methylamine 

N NHCH3 NH2

 Pyridine  N-Methyl aniline  Aniline

 

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬٢ J٢ J٨
 W‫א‬‫א‬W
‫א‬amine‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
CH3 CH3
CH3NH2
o CH3 NH CH3 N CH3
o
Methylamine (1) o
Dimethylamine (2)
Trimethylamine (3)

CH3 CH3

CH3CH2CHNH2 CH3CH2- N - CH3

o
sec-Butylamine (1) Ethyldimethylamine(3ْ)
 W‫א‬‫א‬‫א‬‫א‬
NH2
Cl NH(CH3)
Cl
NH2
NO2

Cl
O-Nitroaniline 2,4,6-Trichloroaniline N-Methylaniline
‫א‬‫א‬‫א‬‫א‬‫א‬

CH3 NH2

p-Toluidine

 KP- Toluidine‫א‬Toluidine‫א‬Aminotoluene
‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

N N
N N N
H H
H
Pyrrolidine Pyrrole Quinoline
Pipyridine Pyridine
 W‫א‬‫א‬W 
‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬Amino
‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬
CH3 CH3 CH CH2 CH CH3
CH3 CH2 CH CH2 CH CH3 NH2
NH2

5-Methyl -3-aminohexane
2-Amino-4-phenylpentane
H2N CH2 CH2 CH2 COOH CH3 CH NH CH2 CH3

4-Aminobutanoic acid CH2CH2CH2CH3

2-(N-Ethyl amino)hexane
COOH

NH2

P-Aminobenzoic acid
 W‫א‬W 
EAmmoniumFEAmineF
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬(Anilinium)EAnilineF‫א‬
 W‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

_
+
NH3 Br
CH 3 _
+
CH3-N-CH 3 I
CH 3
Anilinium bromide
  Tetramethylammonium
 W‫א‬‫א‬‫א‬٣ J٨
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 (C2H5)2NH, (CH3)3N, (CH3)2NH, CH3NH2 WEF‫א‬‫א‬
E١١ J٤F‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬E11F
 K‫א‬‫א‬‫א‬‫א‬
، 
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K
 
‫א‬‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KE8-1F‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬E8-1F‫א‬
‫א‬  
‫א‬ ‫א‬‫א‬
 ‫א‬
  - 42 44 Propane CH3CH2CH2
   17 45 Ethylamine
CH3CH2NH2
  7.5 45 Dimethylamine CH3NHCH 3
  78 46 Ethyl alcohol
CH3CH2OH
  100.5 46 Formic acid
HCOOH
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬،‫א‬‫א‬K‫א‬‫א‬‫א‬،
 K‫א‬
- ١٢٠ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬٤ J٨
،‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬
  ‫א‬
 K‫א‬‫א‬
_
+
 RNH 2 + HX
[ RNH 3 ] X
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
π‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬‫א‬

. NH2 +
NH2
+
NH2
+
NH2


[ _

_
_
]
Resonance structures of aniline
 E‫א‬‫א‬‫א‬F
‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬
 K‫א‬–SO3H‫א‬–NO2‫א‬
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬، ‫א‬ ‫א‬–OCH3‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬
NH2 NH2 NH2

> >
OCH 3 NO2

‫ﺗﻘﻞ اﻟﻘﺎﻋﺪﻳﺔ ﺑﺎﺗﺠﺎﻩ اﻟﺴﻬﻢ‬

 
- ١٢١ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬ ‫א‬ 
،‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬Kb

+ _
R NH 2 + H2O R NH 3 + OH

Alkylammonium ion
  Amine
+ _
[ R _ NH3] [ OH ]
Kb =
[ _
R NH2 ]
 
‫א‬KK‫א‬Kb 
 ‫א‬ pKb  Kb‫א‬‫א‬
 W‫א‬‫א‬‫א‬ pKb

NH2
 NH3  CH3NH2  (CH3)2 NH
 
_ 10 _5 _4 _4
K b = 4.2 * 10 K = 1.8 * 10 K b= 4.4 * 10 K b= 5.1 * 10
  b  
pK b= 9.38 pK b= 4.74 pK b= 3.36 pK b= 3.29
    
     
 (CH3)3 N
pK b= 4.26      
 
_
10
     
K b = 5.5 * 10

 
 

- ١٢٢ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬٥ J٨
 W‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬W 
 W‫א‬‫א‬
 W‫א‬‫א‬  J
_
+ OH
H3N + R X R NH 3 X R NH 2 + H2O + X
o
Alkyl halide Primaryamine 1
 
 W‫א‬‫א‬‫א‬  J

1) CH3Cl
CH3CH2NH2 CH 3CH2NH
2) OH
CH 3

‫أﻣﻴﻦ أوﻟﻲ‬ ‫أﻣﻴ ﻦ ﺛ ﺎﻧﻮي‬

o o
(1) (2)
 
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬–
‫א‬ ‫א‬K‫א‬‫א‬‫א‬‫א‬‫ א‬K
LIAIH4‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
H2 / Pt
CH3 NO2 CH3 NH2

Nitromethane Methylamine

+ _
Fe / HCl Na2CO3
NO2 NH3Cl NH2

 K‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬K
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬LIAIH4‫א‬
 K‫א‬

- ١٢٣ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

H2 / Pd or
CH3CH2 C N CH3 CH2 CH2 NH2
LiAlH4 / Ether

H2 / Pd
C N CH2 NH2

‫א‬‫א‬Hofman degradation‫א‬W
NaOBr‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬E‫א‬‫א‬‫א‬F

O
4NaOH
CH3(CH 2)4 C NH2 + Br2 CH3(CH 2)4 NH2 + By Products
H 2O

‫א‬‫א‬‫א‬ ‫א‬، ‫א‬‫א‬

 W
 K‫א‬‫א‬‫א‬  J١
KNitroalkanes‫א‬‫א‬‫ א‬ J٢
‫א‬‫א‬‫א‬‫א‬  J٣
‫א‬Nitrobenzene‫א‬‫א‬‫א‬Phenylamine
K‫א‬‫א‬‫א‬‫א‬‫א‬

- ١٢٤ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬٦ J٨
 W‫א‬‫א‬
 W‫א‬HCl‫א‬‫א‬‫ א‬ J١
+ _
CH3 CH2 NH2 + HCl CH3 CH2 NH3 Cl
_
+
(CH3)3 N + HCl (CH3)3 NHCl
 WNitrous acid‫א‬‫ א‬ J٢
‫א‬‫א‬–‫א‬‫א‬‫א‬‫א‬  J
E٥ J F ‫א‬‫א‬ NaNO2
K ‫א‬‫א‬‫א‬Diazonium salts‫א‬
‫א‬‫א‬،‫א‬‫א‬  ‫א‬
K‫א‬‫א‬‫א‬
O
0-5 C +
Ph NH2 + HNO2 Ph N2

Diazonium ion
 
‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬  J

‫א‬‫א‬‫א‬‫א‬‫א‬ENaNO2HCl
‫א‬‫א‬
 ‫א‬‫א‬‫א‬ ،‫א‬
 KEFNitrosoamine
‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
CH 3 (CH 2)4 CH 2 NH 2 HNO2
‫א‬ + N2
o
(1) amine

- ١٢٥ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

CH3(CH2) NH N=O
+ H 2O
o HNO2 CH3 CH2-N-CH 2 CH3 + H2O

  2 amine  N-Nitrosodiethylamine

HNO2 
 (CH3 CH2)3 N No reactions.
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  J٣
 ‫א‬ J  ‫א‬ J  ‫א‬ J
 W‫א‬‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
 K
NH2 NH2

Br2 / H2O

Br Br
Br

Aniline 2,4,6-Tribromoaniline
‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،
NH2 NHCOCH3 NHCOCH3 NH2

+
(CH3CO)2O Br2 H2 O / H

Br
Br
Aniline Acetanilide p-Bromoacetanilide p-Bromoaniline
 W‫א‬‫א‬ K٢
‫א‬‫א‬‫א‬‫א‬
  ‫א‬‫א‬–N+H3‫א‬‫א‬
p- Nitroaniline 
 ‫א‬‫א‬‫א‬
 W‫א‬

- ١٢٦ -
  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

NH2 NHCOCH 3 NHCOCH 3 NH2

O +
(CH3CO)2O H2SO4/15C H2O/H
H2 O

NO2 NO2
P-Nitroacetanilide P-Nitroaniline
 
 
 W‫א‬‫א‬ K٣
–‫א‬‫א‬‫א‬‫א‬‫א‬
 K
_
+ +
NH2 NH3HSO4 NH3

O
H2SO4 180-200 C

_
SO3
Aniline Anilinium hydrogen
Sulphanilic acid
sulphate

 W‫א‬‫א‬‫א‬٧ J٨
 ‫א‬،
،‫א‬‫א‬H2N-(CH2)6-H2N"1,6-hexamethylenediamine"
hexamethylenediamine
  
٢٧٠‫א‬C6H12N4W‫א‬‫א‬‫א‬،urotropin
،EformaldehydeF‫א‬‫א‬Ko
 o٩٥‫א‬E٪٢٧F‫א‬E٪٣٠F‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬، octogen‫א‬hexogen‫א‬
 C6H5-NH2 aniline‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
، ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

،‫א‬‫א‬‫א‬ ‫א‬‫א‬
‫א‬‫א‬‫א‬،EhydroquinoneF
 KE‫א‬F‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬
 K،
 
 
 

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  ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 W‫א‬‫א‬‫ א‬K١
1) CH3 CH2 N(CH3)2 2) CH3 CH2 CH CH3
NH2

+ _ 4) CH3 CH CH2 CH2CH2

3) CH3 CH2 N(CH3)3I
Br NH2

5) NH2 6) CH CH2 CH2

NH2 OH
Br
 W‫א‬‫א‬‫ א‬K٢
1) Cyclopentylamine . 2) B-phenylethylamine .
3) 1,6-Hexamethylendiamine . 4) Benzylamine .
5) N,N-Dimethylamine . 6)tetra-n-Butylammonium
iodide .
7) P-Aminobenzoic acid .
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣
1) CH3 CH2 CH NH2 _
+
2) (CH3)3 NHNO3
CH3

4) (CH3CH2) C NH2
3) NH

_
+
5) N(CH3)2 Cl 6) NCH3

_
+
7) N(CH3)2 8) (CH3)2 CH N (CH3)3 Br

 K‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٤
 W ‫א‬‫א‬ K٥

O2N NH 2
, CH 3O NH 2 , NH 2 (A
   

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 ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

  NH3
,  (CH3)2 NH
, (CH3)3 N ,  CH3-C-NH2 (B
 W‫א‬‫א‬ K٦
1) CH3Cl
a) (CH 3CH2)2 NH
2) OH
?

Br Br
?
b)
NO2 NH2

H2 / Pt

c) CH3CH2CN ?
O
d) CH3CH2 C NH2 + Br2
4NaOH
?
H2O

+ _

 e) CH3NH2 +
? CH3 NH3Cl

 f) (CH 3CH2)2 N CH 3
HNO2
?
NH 2 NH 2
Br Br
g)
+ ?
Br


h) NH2 + CH3Cl ?

 
 
 

- ١٣٠ -
 ‫א‬‫א‬  ١٥٣  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
 WE1F‫א‬‫א‬
1) Ethyl dimethyl amine . 4) 1-Amino-4-bromo pentane .
5) O- bromo aniline .
 WE٢F‫א‬‫א‬
CH 2NH 2
(4 NH 2 (1
 
 
  +
_
(CH 3CH2CH2CH2)4 N I (6

 WE٣F‫א‬‫א‬
 KE3  KE2
 KE6  KE4
 WE٥F‫א‬‫א‬
 P-methoxy aniline > Aniline > P-Nitro aniline .
 WE٦F‫א‬‫א‬
CH3CH 2CH2 NH2 (c (CH 3CH 2)2 N CH 3 (a
 K (f HCl (e
 
 

- ١٣١ -
 ‫א‬‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬

 ‫א‬‫א‬
 W‫א‬‫א‬‫א‬
‫א‬W‫א‬،‫א‬‫א‬‫א‬K‫א‬‫א‬، K١ 
 ١٩٨٩
١٩٩٠‫א‬W‫א‬،‫א‬‫א‬K،‫א‬،‫ א‬K٢ 
 ١٩٩٦،‫א‬،‫א‬،‫א‬‫א‬K،‫ א‬K٣ 
 ١٩٩٨،‫א‬،‫א‬،‫א‬K‫א‬، K٤ 
،‫א‬‫א‬‫א‬K،‫א‬‫א‬،‫א‬،‫ א‬K٥ 
 ٢٠٠٠،‫א‬،‫א‬

 W‫א‬‫א‬‫א‬W
1.Fessenden, Ralph J.and Fessenden, Joan S. Organic Chemistry ,2nd ed, PWS, Boston
1982.

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 ‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬

 ‫א‬
  J٢ J  K K K K K K K K K K K K K K K K K K K K K K K K K W١ J١
  J٣ J  K K K K K K K K K K K K K K WFunctional Group‫א‬‫א‬٢ J١
  J٥ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J١
  J٨ J  K K K K K K K K K K K K K K K K K K K K K K K K K K K 
  J٩ J  K K K K K K K K K K K K K K K K K K K K K K K ١ J٤‫א‬‫א‬
  J١١ J K K K K K K K K K K K K K K K K K K K K K K K K W‫א‬١ J٢
  J١١ J K K K K K K K K K K K K K K K K K K K W‫א‬ J
  J١١ J K K K K K K K K K K K K K K K K K K K K WAlkanes‫א‬٢ J٢
  J١٣ J  K K K K K K K K K K K K K K K K WAlkyl Group ER-F‫א‬
  J١٤ J K K K K K K K K K K K K K K K WCycloalkanes ‫א‬‫א‬
  J١٥ J  K K K K K K K K K K K K K K KWIUPAC‫א‬‫א‬‫א‬
  J٢٢ J K K K K K K K K K K K K K K K K K K K K KWalkenes‫א‬٣ J٢
  J٢٨ J K K K K K K K K K K K K K K K K K KW‫א‬‫א‬W
  J٣١ J  K K K K K K K K K K K K K K K K K K K K WAlkynes‫א‬٤ J٢
  J٣١ J  K K K K K K K K K K K K K K K K K K K K W‫א‬١ J٤ J٢
  J٣٤ J  K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬‫א‬
  J٣٨ J K K K K K K K K K K K K K K K K K K K K K K2-5
  J٤٠ J K K K K K K K K K K K K K K K K K K K K K K٢ J٥‫א‬
  J٤٢ J  K K K K K K K K K K K K K K K K K K K K K K K K KW١ J٣
  J٤٢ J  K K K K K K K K K K K K K K K K K K K K K K W‫א‬٢ J٣
  J٤٣ J  K K K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬٣ J٣
  J٤٤ J K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬٤ J٣
  J٤٤ J K K K K K K K K K K K K K K K K K K K KW‫א‬٥ J٣
  J٤٨ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٦ J٣
 ‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬

  J٤٨ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٧ J٣

  J٥١ J  K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٨ J٣
  J٥٣ J K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬٩ J٣
  J٥٤ J  K K K K K K K K K K K K K K K K K K K K K K K 
  J٥٦ J K K K K K K K K K K K K K K K K K K K K K K ٣ J٨
  J٥٨ J K K K K K K K K K K K K K K K K K K K K K K K K K W١ J٤
  J٥٨ J K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٢ J٤
  J٥٩ J K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٤
  J٥٩ J K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٤ J٤
  J٦١ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٤
  J٦٣ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٦ J٤
  J٦٤ J K K K K K K K K K K K K K K K K K K K K K K K 
  J٦٦ J  K K K K K K K K K K K K K K K K K K K K K K ‫א‬
  J٦٨ J  K K K K K K K K K K K K K K K K K K K K K K K KW١ J٥
  J٦٩ J K K K K K K K K K K K K K K K K K K K K K KW‫א‬٣ J٥
  J٧١ J K K K K K K K K K K K K K K K K K K K K K K K KW‫א‬
  J٧٢ J K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٤ J٥
  J٧٣ J K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬٥ J٥
  J٧٥ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٦ J٥
  J٧٨ J K K K K K K K K K K K K K K K K K K K K K KE‫א‬‫א‬F
  J٨٢ J K K K K K K K K K K K K K K K K K K K K K K K K KW١ J٦
  J٨٢ J K K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٢ J٦
  J٨٣ J K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬
  J٨٤ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٦
  J٨٥ J K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٤ J٦
 ‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬

  J٨٦ J  K K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬W
  J٨٦ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٦
  J٨٧ J K K K K K K K K K K K K K K K K K K K K K KE‫א‬‫א‬F
  J٨٩ J K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J٩١ J  K K K K K K K K K K K K K K K K K K K K K K K K K W١ J٧
  J٩١ J  K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٢ J٧
  J٩٣ J K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬‫א‬٣ J٧
  J٩٤ J  K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٤ J٧
  J٩٥ J K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٥ J٧
  J٩٨ J K K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J٩٩ J K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J١٠١ J  K K K K K K K K K K K K K K K K K K K K K K K KW١ J٨
  J١٠١ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬٢ J٨
  J١٠٣ J  K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٣ J٨
  J١٠٤ J  K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٣ J٨
  J١٠٤ J  K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٤ J٨
  J١٠٦ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٨
  J١٠٧ J  K K K K K K K K K K K K K K K K KW‫א‬‫א‬٦ J٨
  J١٠٨ J  K K K K K K K K K K K K K K K K KW‫א‬‫א‬٧ J٨
  J١٠٩ J  K K K K K K K K K K K K K K‫א‬‫א‬١ J٧ J٨
  J١١٢ J  K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J١١٤ J  K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J١١٧ J  K K K K K K K K K K K K K K K K K K K K K K K K W١ J٨
  J١١٧ J  K K K K K K K K K K K K K K K K K KW‫א‬٢ J٨
  J١٢٠ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٨
 ‫א‬ ١٥٣ ‫א‬
‫א‬‫א‬ ‫א‬

  J١٢١ J  K K K K K K K K K K K K K K K K K K K K KW‫א‬٤ J٨
  J١٢٥ J  K K K K K K K K K K K K K K K K K K K K W‫א‬٦ J٨
  J١٢٩ J  K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J١٣١ J  K K K K K K K K K K K K K K K K K E‫א‬‫א‬F
  J١٣٢ J  K K K K K K K K K K K K K K K K K K K K K K K K K K‫א‬‫א‬
  J١٣٢ J  K K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬
  J١٣٢ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬W
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