5 ,

:
.
.

.

.
.
sp
.
sp2 .
sp3 .

.

.

.
.

.

104.

:
:
. .
, .
. ,
. ,
.
. , .
. , .
:
:
. ,
.
. ,
spin .
.
.
, .
:
s s, s p p p , .
.
,
. ,
. .

 -
1

105.

:
p p ,
. ,
,

. ,
. s , , .
, s , .
, .
() ,
(=) () .
, ( )
,
.
:
. .
.
, , .
. .
. , .
:
sp s
p .
sp
50% s 50%
p.
sp2 s
p .
sp2
120.
sp3 s
p .

106.

sp3
109,5.
:
(C C):
T , sp3
,
sp3 sp3.
(C = C):
T , sp2 .
sp2 sp2 p p.
(C C):
T , sp . sp sp p p.
: C C < C = C < C C
:
( ) :
. : 12 , 275 283.
. : 12 , 283 285.
. : 13 , 301 306.
. : 13 , 306 308.
. - : 14 , 325 330.
. - : 14 , 330 333.
. : 15 , 351 352.

 -
1

107.

CvH2v+2
CvH2v CvH2v-2
R-C C-R1
R-C C - H,
HC CH
R-OH
R-O-R 1
R-CH2OH
R
CH-OH
R1
R
R1 C - OH
R2
R - CH = O
R-C-R 1
O
CH3CH2O
R - CH2OH
CH3CH = O
R - CH=
R - CH - CH3
OH
R - CH - R1
OH
R - C - CH3
O
R - C - R1
O
R-COOH
R1-COO-R2

HCOOH

/ Br2 CCl4
/
CuCl
a
a

/ KMnO4

OXI

R-C CCu,CuC CCu

R-C Ca, C Ca
2
RONa + 1/2 H2
OXI
R - COOH
R C=
R1

H2

Fehling

Tollens

Cu2O
Ag

I2 a
I2 a

I2 a

I2 a

CHI3

CHI3

CHI3

CHI3

OXI
Na2CO3

CO2

RCOOH

/ KMnO4
/ K2Cr2O7

C6H5OH

R-OH

CO2
OXI
C6H5Oa + 2

108.

.
:
. 259: 43, 44, 45, 46
. 260: 48
. 262: 65
. 263: 66, 68, 70, 71, 73
. 264: 74, 76, 77

. 265: 86, 91, 92

. 266: 94, 95, 96, 97, 100
. 267: 101, 103
. 268: 104, 105, 106, 108
. 269: 109, 111, 112, 113

. 11 15
(
, )
:
(11 15 )
. 336: 4
. 268: 1, 2
. 340: 7
. 287: 3
. 356: 1, 2
. 290: 5
. 358: 5
. 311: 4
. 359: 7
. 314: 7
. 362: 9
. 335: 3
:
(11 15 )
. 274: 1, 3
. 274:
. 298: 7, 8, 9, 10, 11
. 299: 15, 16, 17
. 300:
. 321: 7, 8, 9
. 322: 10, 12, 13

. 347: 11, 12, 13, 14

. 348: 15, 16, 18
. 349:
. 368: 3, 6
. 369: 11, 12, 14
. 370: 15, 16, 18
. 371: 19, 22, 13

 -
3

109.

1. . ;
. 600 mL r2
CCl4 16,2 g.
;
. . 1
a. S.T.P.
;
. 2 HgSO4
2SO4. ;
. 3 CuCl.
g ;
: = 1, C = 12, Br = 80, Cu = 63,5.
:
: CHy. H 2 :
CHy + 2 CH2+2
o 2 , = 2.
: y + 2 = 2 + 2 y + 4 = 2 + 2 y = 2 2
: CH2 2, .
. : C22 + 2Br2 C22r4
100 mL 16 g Br2.
: x = 96 g Br2
600 mL x; g Br2.
m Br2
96g
n Br2 =
=
= 0,6 mol
MrBr2 160g / mol
1 mol A 2 mol Br2.
: = 0,3 mol A
mol A 0,6 mol Br2.

110.

H .
, 0,3 mol A 16,2 g.
m
m
16, 2g
= 54g / mol
n A = A MrA = A =
MrA
n A 0,3mol
: rA = ArC + (2 2)rH = 14 2
: 14 2 = 54 = 4
: C4H6
. a,
CH
. : CH3CH2C
CH3CH2CCH + a CH3CH2CCNa + 1/2 H2
H 0,1 mol.
1 mol A 1/2 mol 2.
: z = 0,1/2 mol H2
0,1 mol A z; mol 2.
O 2 S.T.P. : VH2 = nH2 Vm = 0,1/2 mol 22,4 L/mol = 1,12 L
.
.
. CH3CH2CCH + CuCl + NH3 CH3CH2CCCu + NH4Cl
1 mol A 1 mol CH3CH2CCCu.
: = 0,1 mol CH3CH2CCCu.
0,1 mol A ; mol CH3CH2CCCu.
r CH3CH2CCCu : r = 4ArC + ArH + ArCu = 116,5
: m. = n Mr = 0,1 mol 116,5 = 11,65 g

2. . 1 V mL KMnO4 0,2 , H2SO4 . 2

(a) 0,2 mol . 3 2 1,2 mol CO2. :
. .
. KMnO4
.
:
: C2+1, : C2+1
3x mol A 3x mol B.

 -
3

111.

2
,
, .
2 , , , CH3CH2OH ( = 2).
CH3CH2OH + 4I2 + 6NaOH CHI3 + HCOONa + 5NaI + 5H2O
mol : 3x/3 = x mol
:
1 mol 1 mol CH3I.
x mol 0,2 mol CH3I.
x = 0,2
:
C2+1 + 3/2 O2 CO2 + (+1)2 (1)
(2)
C25 + 3O2 2CO2 + 32
(1) :
1 mol
mol C2.
0,2 mol ; mol C2.
= 0,2 mol C2.
(2) :
1 mol C25 2 mol C2.
0,2 mol C25 ; mol C2.
= 0,4 mol C2.
mol CO2 1,2, :
0,2 + 0,4 = 1,2 = 4, : C4H9OH.
. C4H9OH,
. , : CH3CH2CH2CH2OH
B : CH3CH2OH
. n4 :
5CH3CH2CH2CH2OH + 4KMnO4 + 6H2SO4 5CH3CH2CH2COOH + 4MnSO4 + 2K2SO4 + 11H2O

5CH3CH2OH + 4KMnO4 + 6H2SO4 5CH3COOH + 4MnSO4 + 2K2SO4 + 11H2O

:
5 mol 1- 4 mol nO4.
0,2 mol 1- ; mol nO4.
= 0,16 mol nO4.
:
5 mol 4 mol nO4.
0,2 mol ; mol nO4.

112.

= 0,16 mol nO4.

, mol KMnO4 : (0,16 + 0,16)mol = 0,32 mol.
n
n 0,32mol
= 1,6 L
: c = V = =
V
c
0, 2M

3. C5H10O 8,6 g. . 1 4,29 g . 2

(a) .
mol
.
: rC5H10O = 86, rCu2O = 143
:
C5H10O :

2x mol 2 mol .
: mA + mB = m. 2x 86 + 2 86 = 8,6 x + = 0,05
1 x mol A mol B. ,
. ( ),
, :
CH3CH2CH2CH2CH = O + 2CuSO4 + 5NaOH CH3CH2CH2CH2COONa + Cu2O + 2Na2SO4 + 3H2O

:
1 mol 1 mol Cu2O.
= x mol Cu2O.
x; mol ; mol Cu2O.
n Cu 2 O =

m Cu 2 O
MrCu 2 O

x=

4, 29g
= 0,03mol
143g / mol

x + = 0,05 = 0,05 x = 0,02 mol

H 3-, 2- 2.
0,06 mol 0,04 mol 3-.

4.

Mr = 130 . 2/a , HCl ,

 -
3

113.

, , .
,
;
: rH = 1, ArC = 12, ArO = 16.
:
: C2+1CCH2+1.
:
+

C 2 +1COOC 2 +1 + 2
C 2 +1COO + C 2 +1
+

, : C2+1C
: CH2+1.
H , : CH2+1CH()CH3.
: + 2 = (1)
:
CH2+1CH()CH3 + 42 + 6aOH CHI3 + C2+1COONa + 5NaI + 5H2O
Cl :
C2+1COONa + Cl C2+1COO + aCl

. , : C2+1COO.
, = (2)
: rA = 130 ( + + 1)rC + (2 + 2 + 2)ArH + 2rO = 130
+ = 6 (3)
(1) (2) (3) : = = 2, = 4
: CH3C2COOC4H9, : CH3CH2COOH : C3CH2CH(OH)CH3.
:

114.

.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
1.
.......................................................................................................................................

.
.......................................................................................................................................
;
.......................................................................................................................................
. 2 .
.......................................................................................................................................
1
.......................................................................................................................................
400 mL 8% w/v .......................................................................................................................................
11,2 g.
;
.......................................................................................................................................
. 2 2
.......................................................................................................................................
. mol
.......................................................................................................................................
;
.......................................................................................................................................
.
.......................................................................................................................................
.......................................................................................................................................
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 -
4

115.

2.
. ,
.......................................................................................................................................
, , , , , , , , , .
.......................................................................................................................................
()
.......................................................................................................................................
2SO4
+ Cl2
+ 2
+ aOH
Fehling
B

[ ] E
Z
C 2 +1
gSO4 / H 2SO4
ROH
170 o C
.......................................................................................................................................
+ SOCl2
+ 2
+ 2 / aOH
+ Mg
+
.......................................................................................................................................
A

H


+ CHI3

.......................................................................................................................................
nO 4
Cu
A

M
H 2 SO 4
.......................................................................................................................................
(o)
.......................................................................................................................................
. 9,2 g
100 mL aOH 1 ,
.......................................................................................................................................
pH .
.......................................................................................................................................
: rH = 1, ArO = 16, ArC = 12 aM = 105.
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
.......................................................................................................................................

116.

3.
:
.......................................................................................................................................
.
.......................................................................................................................................
KMnO4 / H2SO4.
.......................................................................................................................................
a / 2 .
.......................................................................................................................................
.......................................................................................................................................
.
.......................................................................................................................................
. RMgCl .
.......................................................................................................................................
. 0,6 mol
.......................................................................................................................................
2/3. mol ; ;
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................

 -
4

117.

4.
6 mol , C4H10O
.......................................................................................................................................
, .
.......................................................................................................................................
1 (a) .......................................................................................................................................
394 g .
.......................................................................................................................................
2 1000 mL H2SO4
.......................................................................................................................................
KMnO4 0,4 .
mol , ;
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................

118.

5.
]
.......................................................................................................................................
. 1 2
.......................................................................................................................................
Ni 0,6 g .
.......................................................................................................................................
2 (a)
.......................................................................................................................................
39,4 g .
.......................................................................................................................................
. mol;
.......................................................................................................................................
. :
.......................................................................................................................................
1. Tollens. 2. A Fehling. 3. CH3MgCl
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................

 -
4

119.

6.
6 mol C3H7Cl .......................................................................................................................................
a .
.......................................................................................................................................

.......................................................................................................................................
KMnO4 H2SO4.
.......................................................................................................................................
2 L a 2.
.......................................................................................................................................
. mol ;
.......................................................................................................................................
. .
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
.......................................................................................................................................

120.

7.
, .......................................................................................................................................
4 . 1
.......................................................................................................................................
44,8 L S.T.P. 2 .......................................................................................................................................
4 L KMnO4 0,7 H2SO4.
.......................................................................................................................................
3 (a) 1970 g
.......................................................................................................................................
( = 394).
.......................................................................................................................................
. mol ,
;
.......................................................................................................................................
. 4 . L .......................................................................................................................................
S.T.P.;
.......................................................................................................................................
Mg Ca n L
.......................................................................................................................................
S.T.P.;
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
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 -
4

121.

8.
.......................................................................................................................................
. 26,09%
.......................................................................................................................................
, 60% . .......................................................................................................................................
(2 / a) , .......................................................................................................................................
, .
.......................................................................................................................................
. :
.......................................................................................................................................
4. NH3
1. a
2. a
3. a2C3
.......................................................................................................................................
. :
3. SOCl2,
1. Na
2. H2SO4()/170 C
.......................................................................................................................................
4.

KMnO
4
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................

122.

9.
.......................................................................................................................................
C6H12O2:
.......................................................................................................................................
.......................................................................................................................................
C3H6O2 .
.......................................................................................................................................

.......................................................................................................................................
C3H6O.
.......................................................................................................................................
. , ,
, .
.......................................................................................................................................
. :
.......................................................................................................................................
1. SOCl2 KOH;
.......................................................................................................................................
2. (2 / a);
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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 -
5

123.

.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
1
.
;
.......................................................................................................................................
( 5)
.......................................................................................................................................

.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.
;
.......................................................................................................................................
, .
( 5)
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
CH. .
CH2=CHCH2C
.......................................................................................................................................
: C = 6, H = 1.
( 5)
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.
:
. .
.......................................................................................................................................
. -2- .
.......................................................................................................................................
. 2- .
.......................................................................................................................................
. C3H8O (aOH) .
.......................................................................................................................................

124.

. CuCl.
.......................................................................................................................................
( 10)
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
2
.......................................................................................................................................
.
:
.......................................................................................................................................
. 2-
. 3-
.......................................................................................................................................
. 2--2-
. 1-
.......................................................................................................................................
( 5)
.......................................................................................................................................
.......................................................................................................................................
.
1,3- :
.......................................................................................................................................
.
. Buna
.......................................................................................................................................
.
.
( 5)
.......................................................................................................................................
.......................................................................................................................................
.
;
.......................................................................................................................................
. 3-
.
.......................................................................................................................................
. 3--2-
. 2-
.......................................................................................................................................
( 5)
.......................................................................................................................................
. :
.......................................................................................................................................
. aOH
. Na2CO3
.......................................................................................................................................
. a
. Br2 CCl4
.......................................................................................................................................
( 5)
.......................................................................................................................................
E.

.......................................................................................................................................
:
.......................................................................................................................................
. CH3CH2COOCH3 + NaOH .................... + ....................
.......................................................................................................................................
. CH3CN + 2H2 ....................
.......................................................................................................................................
+[O]
+[O]
....................
....................
. RCH2OH
2
.......................................................................................................................................
+
H
. CH3CN + 2H2O .................... + ....................
.......................................................................................................................................
+ H2O
.................... + ....................
. HCH=O + (CH3)2CHMgBr ....................
.......................................................................................................................................
( 5)
.......................................................................................................................................

 -
5

125.

3
.......................................................................................................................................
.

.......................................................................................................................................
, :
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
( 13)
.......................................................................................................................................
.......................................................................................................................................
.
1-, , , 1,
2- .
.......................................................................................................................................
,
.......................................................................................................................................
: a2CO3, CuCl NH3, Br2 CCl4
.......................................................................................................................................
Fehling;
.......................................................................................................................................
( 12)
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................

126.

4
.......................................................................................................................................

, () .......................................................................................................................................
. 1 a , .......................................................................................................................................
4,48 L , S.T.P. 2
.......................................................................................................................................

(a) ,
.......................................................................................................................................
118,2 g . 3 H2SO4

nO4 0,2 .......................................................................................................................................

,
800 mL .
.......................................................................................................................................
mol ;
.......................................................................................................................................
( 25)
.......................................................................................................................................
.......................................................................................................................................
.......................................................................................................................................
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.......................................................................................................................................
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.......................................................................................................................................
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