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HANDBOOK
ALLEN
CAREER INSTITUTE KOTA IRAJASTHAN
- FAST REVISION
ALLEN
CAREER INSTITUTE
MASLIETAV
ORGANIC CHEMISTRY
CHONSORS
Chemistry HandBook
-
-
ALLEN
Prefix
Functional group
Structure
Suffix
Carboxy
- oic acid
Carboxylic acid
Sulphonic acid
-C-OH -SO,H
Sulpho
sulphonic acid
Anhydride
oic-anhydride
Alkoxy carbonyl
Ester
alkyl....oate
OR
or Carbalkoxy Chloroformyl or
|- oyl chloride Chlorocarbonyl
Acid chloride
Acid amide
Carbamoyl/
Amido
- amide
- NHÀ
Carbonitrile/Cyanide
-CEN
Cyano
nitrile
Keto or oxo
- one
Alcohol
-OH
- ol
Thio alcohol
-SH
Hydroxy Mercapto
Amino
thiol
Amine
-NH,
amine
Ether
Alkoxy
-O-R
Ç-C
Oxirane
Epoxy
Nitro derivative
-NO,
Nitroso derivative
-NO
Nitro Nitroso
WIDHIWEDDA
Halide
Halo
Double bond
C=C
ene
Triple bond
| CEC
yne
98
CHAT
Chemistry HandBook
ALLEN
ISOMERISM
Сотр-сип nionis org
emical or biological properties
DEFINITION Compounds having same molecular formula but differ in atleast one physical or chemical or
biological promo
diethyl ether
Cis one bor OPE and
(ii) I
TAUTOMERISM This type of isomerism is due to spontaneous
interconversion of two isomeric forms into each other wa different functional
groups in dynamic equilibrium Conditions:
(iv)
Calcu
e.g.C.H.(CH),: ON
H. CH o-xylene m-xyling
Payler FUNCTIONAL ISOMERISM It occurs when
compounds have the same molecular formula but different functional groups. 2..
CHÁN; CH-CH-CH, - NH,
Isproponamine CH, CH - NH - CH. N-methylathanamine
CH, CH, - N - CH. N. N dimethylmethanamin
Presence of -C- OL-N -> 0 Presence of at least one a-Hatom which is attached to a saturated C-atom.
e.g. Acetoacetic ester
Uns
ubochowa
SYTI
ОН
anol form
Chemistry Handbook
(B)STEREOISOMERISM he same molecular formula and
structural formula but having difference in the spatial arrangement of in 3D space are
called stereoisomers and the phenomenon is called stereoisomerlsın.
TYPES OF STEREOISOMERISM
pourids with the same mol
s or groups in 3D sn
rties
GEOMETRICAL ISOMERISM
han to restricted rotation and is observed in folle
ms
CEN-OH
ler with 2 same
Ring greater than 7 member with double bord)
TECH.
CH
al group
position
attached
Unsymmetrical Symmetrical
21+2 m-
на əлеуметНАНІлливерзнисланнннно раност на
Rule-3
(lf n is even)
I lowest priority is bonded to horizontal line then moving
Clockwise
m=
(If n is odd)
2
0-0
Anti clockwise.R
101
211
Symmetrical Il n = odd
Zin-1_21-12
2
-12
"Where n = no, of chiral carbon The different arrangement of atoms in space
that results from the carbon-carbon single bond free rotation by 360° are called
conformations or conformational isomers or rotational isomers and this
phenomenon is called conformational isomérism
CONFORMATIONAL ISOMERISM
Neumann projection : Here two carbon atoms forming the o bond are represented one
by circle and other by centre of the circle. Circle represents rear side and its centre
represents front side carbon. The C-H bonds of front carbon are depicted from the
centre of the circle while C-H bond of the back carbon are drawn from the
circumference of the circle.
NELTE
Thay
91
Philly bude
al
«K«pk - Ph) C
(Ph) CH> -CH=CH-CH-CH2
i) H02 CH = CH >NH, (CH3C-
(CH2CH2CH, CH, CHẠCH, CHCH=C
0 CH = CH = CH = CH - CH-CH, (B) Stability
of free radical
(vii) CH,
Phenol >m >p> In aqueous
medium
CH, R=CH 2 >1"> 30 > NH. R ==CH-CH 2
3 >1">NH,
p>o >m > Phenol In gaseous
medium R = CH 3 >2 > 1 >NH. R CH CH 3 > 20 21 NH.
ОН Reactfulty towards nucleophile (NAR)
(1) HCHO > CH CHO > (CH) CÓ (2) CCI,CHO > CHCI,CHO > CH CICHO
NO. Reactivity order towards acyl
nucleophilic substitution reaction
) CHE Acid chloride > anhydride > ester > amide
0>p>m > benzoic acid Order of
electronle effect
COOH Mesomeric > Hyperconjugation >
Inductive effect |xi) C,H, Stability of alkene no. of -hydrogen
Khu G H, 104
(ix) CH, OH
as soon one
COOH
NO.
CH,
slom
os Corrn
o >m >
> benzoic acid
Chemistry HandBook
CHAPTER
- MARE
PRACTICAL ORGANIC CHEMISTRY
Confirmed test
Nax
PURIFICATION METHODS
LASSAIGNE'S METHOD
DISTILLATION TECHNIQUES
(detection of elements)
Element
Sodium (A)
SIMPLE DISTILLATION 1B) FRACTIONAL
extract Candidons
difference is IOK
FeCl,
conc. HCIFe Felcu () When boiling point difference
NaCN Examples Is 30 Kor more. Examples
0 Crude oil in d) Mixture of chloroform
petroleum (BP = 334K) and Aniline
industry (BP = 457K)
=P+
) Yellow ppl Insoluble in K P
NH,
CUTILITTI 3 | immiscible with water and Vapour Vapour Vapoter steam volatile.
pressure pressure pressure Example:
of of water (1) Anline is weparated
Organic liquid
Nitrogen Na+C+N+S
As in test for
nitrogen instead from water
green or blue
colour blood (ii) Turpentine oil ) Nitro Benvene
colouration
conlims PRSES (iv) Bromo Bervene (v) Naphthalene
together NaCNS
of N and S
both (vi) o-Nitrophenol
Sed u hibe
را دارای
um sulphate which is ess of alkali to liberale
70 ON=
Chemistry Handbook
DISTINCTION BETWEEN PAIRS OF
COMPOUNDS
Alde!
UNSATURATION TEST
DISTINCTION BETWEEN 14,2" AND 39 AL
R-C-H+36
R
Lucas Room NPRIN
Aldeh
(a) Double Triple bonded Compounds (C = CVC=C)+ Br, in CCI, (Brown colour) -
Colourless compound
Br Br R-CH=CH-R + Br. R-CH-CH-R
Айните) (Brown)
(Coloneless)
!
R Cloudiness appears
inmediately
Tertiary alcohol
R-C-H
R
R
R-CH-OHSecondary alcohol
LUM toom tema
HC
Br Br R-C=C-R+ Brod, R-¢-C-R
(Akyne) (Brown)
Br Br
(Colourless (b) Double/Triple bonded Compounds +
нс
R-CH. -OH
→ R-CH-CI Primary alcohol
Claudiness appears
R-CH-CH-R + Mno,
ОН он Brown ppa Colourley
.
-R-C-C-R' +KMno. Mno. +RCOOH+R'COOH
(Hot, dilute) Brown Dpt.
• R-C-C-H+KMnO, MnO, +RCOOH+CO+H,0
Alkyne (Hot, dibute) Brown ppt. (Colourless) Baeyer's reagent is cold, dilute KMnO,
solution having pink colour Note : The above test are not given by Benzene. Although it
has unsaturation.
Ag
H
T op tent* CHI + RCOONa
lodoform
Yellow ppt)
chlarida
R-C.CH
Terminal alkona NHẠC +H2O+R-CC-Cu, CuCl + NH4OH
Amines (1
Primar
Rmc
C = 0 + NaHSOR
-C-so Na
R-X + aqueous KOH-
R-OH+Kx-kom
O AgX
Aldehyda
Secon
Precipitate If X is Cl. precipitate will be white and for Br
yellow
Homo
precipitate will be obtained.
ОН -C-SON
HCC = 0 + NaHSOR
Tertiar reactic
Methyl ketone
108
Note: Bent
Chemistry HandBook
ALDEHYDE GROUP
VDS
Chloroethane and chlorobenzene
· CH-Cl+aq. KOHBCH-OH-KCIA CH
While ppt
Tollen's reagent-
Silver mirror
Akehude + Tolla
COHOLS
+2AgNHJJRCOO +2H.0+4NH,+2Ag!
silver nino Lade+Fehling's solution → Reddish
brown precipitate
-CI + ag, KOH
Bali
No reaction
HINO.
CH+2O +5OH+RCOO+3H2O+CuO
(Reddish brown ppt)
form test.
AROMATIC ALDEHYDE GROUP Aromatic aldehyde + Tollen's reagent - Silver mirror
Aromatic aldehyde + Fehling's solution - Negative est
Rhines solation CHO Negative test
Ag + Ag+ coo Silver MUITOI
OH + en KOHO
-CHIRO
-CH+KCI
CH, + aq. KOH Benzyl chlorida)
Agclé UNO
HNO ANG
White ppt
CARBOXYLIC GROUP yuration
Carboxylic acid + Sodium bicarbonate effervescence
Folkek
,HO+CO,
Red ppt
Agim
W !!
• H_C-CH-Cl+aq.KOH No reaction
Vinyl chloride
udrazine -
HCOOH
Telenor sent. 2A + 20% + H.O Formic acid
Silver MiTor NO
AMINES (1)
Caruյնգոլոր
ALLEY
Fehlingen
Ethang
Prommal and propanone (Tollen's and Fehlino o Propanal + Tollen's reagent = >
Silver
CE
Ethyl alcohol and methyl alcohol/lodoform test) . CH.CH OH + 41, + 6NaOH CHI +
HCOONa
Yellow ppt
· HS 10+)- NH
HC-CH2-CH+3OH +2[Ag(NH. - CH,CH,COO +2H0+4NH,+2Ag
(Silver mirror) Propanal + Fehlings solution Reddish
brown prepare
No:
Acetop
Acetone
2. 4-Dinitrophenylhydrazine
ON C-N-NH -NO,
Vellow orange crystals)
2.4-DNP CHOH —
No reaction
HCC = N - NH.
|
HC-CH-CH + 2Cu + OHCH CHCCO + 3H + CI 01
Pieds Souppt Filincs
Negative test Propanone
Tchantcatemi
Negative test
Phenol and ethul alcohol (Neutral FeCl)
• Phenol + Neutral fernic chloride Violet colouration
Pentan-2-one and pentan-3-one (iodoform test)
6 > OH + Fea, 3H* + [Fe(OC,H) + 3HCI
Violet colouration . CH.CH OH + Neutral fernc chloride No violet
H.C.
HefoBN-NH
-10,
Benza
2. 4-DNP 2. 4-DNP
H.C-CH-C-H+2Cu +50H-CH.CH.COO +3H.0000
Fehling's
od
H.C
>>-CHO +2Cu? + 50
No reaction
Propand +2,4-Dinitrophenyihydrazine -->Nocrystals
Acelor
Methul ar
•CH,NH
HC-C-H+ T. + NaOH
Ethara!
= CHI + HCOONa
ladolorm Yellow ppt)
• Ethanoic acid
+ No brown pp!
Toins roumont
H.C NE Dimethy
No silver
110
No silver mim
CHAPTER
Chemistry HandBook
HLAPALEN
Aniline and ethylamine (Diazotisation)
reagent mirror
O
ns Oxia thoni
Aniline
u
doamn
-N - N
-OH
Methana
-N = N
Orange dye p-hydroxy agobername
–
recipitate-stophenone and benzophenone (lodoform test)
OH
SCHOH
= CH.CH.NH.
CH.CH.OH
-
-NH-CH, + CHCI, + 3KOH
No offensive smell
at)
N Methylanine
-C=
>+1 +NaOH
do tet, No ppt.
Benzophenone)
Aniline and Benzylamine (Diazotisation + phenol)
.
.. Ora Croft
-NEN
Aniline
Orange dye
K -CHO+3OH +21Ag(NH)
(Tollen's reagent) K -COO- +2H,O+4NH, +2Ag = action
CH, OH -OH
Benzylamine
No orange dye + Glucose and fructose
Glucose + Br, + HO Gluconic acid + 2HBr
(Broum colour
(Colourless) Fructose + Br, +H,O > Brown colour
(Brown colour)
(no change in colour)
recipitate
+ Cuo + H.O
• CHÚNH,+ CHCl + 3KOH +CHNC + 3KCl + 3H,O. Mehylamina
(alc) Methylisocyanide
Olienske small
Glucose and starch
Glucose + Fehling's solution - Red ppt. Starch + Fehling's solution = No red ppt.
OR Glucose + 1 solution - No blue colour Starch + 1 solution - Blue colour
No offensive smell
MOT
*H,C-NH+CHCI.+3KOH (alc.)
Di-methyl amine
111
HAPTER
ALLE
Chemistry HandBook
- 6 HYDROCARBON - ALKANE
Clamt H
Reduction
PREPARATION
CHBCH H/P1 NH PHI Raney NV/250
C
2 00°C Sahir Sandutens Reduction
TNHH EIU Nu CH CER Un bon
LTI4Lil HC
B
CH CH,
NaOH-CO/A
Sodalmel
C-OH Decarboxylation
NCH
BR (19&2») —
LAIH
CH, | CH CH,
HECH
Br-R (2 & 3) - NaBH,
HiRed
P Hi/Red P H/Red
P
R-X
HI/Red P
R' Zn_
Frankdandection
HC o--
2CH.-Br
2N/Dry etha
Wurtz reaction INoted for en Alia
—ALC
Corey house Good for both smunt, m.alian
REACTION
Cu tube
CH, CHO
HOJHNO,
H
OH
R-NO
HNO, (FRSR) H/SO/400 C
(CH,COOL_M/O.CH-COOH
HC-CH-CHE
H.C-&
da se
Cr,0,/ALLXCH
CH,
HSO, + SO R-SOH
Incomplete (FRSR)
H.O Combustion
3122: ), Aromatization :
CT-0 Al-0.
00.-H.0
Oxidation at 3 H 1773K FRSRU
Isomerization
HC-C-HKMM HC
Anhy. AICI: 773K. 10-20 am
НСТ Reactivity of alkane towards free radical
halogenation is or stability of free radical
Knocking tendency is in the order CH-CH,
SCH,=CH-CH>(CH).CH
Olefin > cucloalkane > aromatis * >
CH-CH-CH=CH-CHÍCH,
Boling point decrease with increase in number
Reactivity of halogen towards free radical substitution
F, > C1, > Br., >1,
CH-CH-CH-CH-CH=CH-CH-CH2-CH2C
Knocking tendency of petroleum as fuel decrease with increase in side chain. Straight chain >
Branched chain
CH,
normal 114
Iso
CH,
смяна начальник на гинекоитонга
sidechair
numbe
/p>CHEL-CH
ALLEN
CHAPTER
Chemistry Handbook
HYDROCARBON - ALKENE
R-CH-CH,
PREPARATION
H SOY OF HIPOVA O ALOVA
HUPAC.co
Ala KOH
Ics Alkenal
HỌC-CEC-CH,
R-CHF-CH Ke Satel
Ba La BHYT Back Reducten
rah Alkene
Rå EH
2n du
HC-CEC-CH,
CH2=CH, CH, CH CHI
R-CH=CH R-CH-CHER
R-CH=
2 din
For High Akun
Parol
R-2-o-CH=CH
Kollaletra
Elimination Reaction
(CH, CH),NOH
C HHHCH
HC-CH-CHSCH
HC-CHCHCH
Dlare substituted alkene is major product
Saytzeff Rule
Less substituted alkent is major product
Hoffman Rule
CH-CH-CH Hoo só h
Cold Conc
HSO, (EAR
REACTIONS
LEH-O-01
(LAR)
+H.C-OH-CH-a
HEX HEL HCLR
(EADO
GONO,
SO Bayan Red
но
он
H
-CH=H.
Ho (EAR)
HO-CH-CH, MR
O-H HC-CH=CH, L ubbock
go
O-H HG-CH-CH, Loremon 1
1 10
siliELD,
H,C-CH-CH H-H CHI
Laxdal
+ HC-CH-CH
HOH the
decor
НОЕ Mah. (LAR)
(EAR
(EARIO
HC-'CH,
H
OHHO (CH-CH=CH
O-H H.C-CH-CH,
foto
+00,-HO +CH-CH=CH,
om
MC (FRSR)
Air
al
MINI
Br
HC-&-94
co-Et-et-
NES
(FESAT) Hloh lemp. / Pressure
Club Brno Ar Murlon
- сна=CH, +91-CHE
HC-CH-CH, -
C-ND 2410
HAC-CH-CH2-04
CH CH CH B
<
>
hain
•
Order of reactivity of olefins for hydrogenation CH=CH, > R-CH=CH,
(Reverse of stability) Order of reactivity of alkene towards hydration
CH-C - CH, >CH, CH = CH, > CH = CH,
ен,
-
115
Chemistry Handbook
ALLEY
CHATTER
HYDROCARBON - ALKYNE
Preparation
HO
_CaC2
Br Br Al. KOH CH-CH, (i) NaNH,
Br
O Alc. KON HỌC-CH 0)
B(i) NaNH, Br Br
Zn dust B-6-6-B
Electric arc/1200 GA.LT Berthelots process
Elimination
H-CEC-H R-CEC-H R-CECER
Kolbe's electrolysis
CH-COOK CH-COOK
Alc. KOH
NaNH or NaH-CEC-R
H,C=CH-CH Alc. KOH
NANH
(II) R-X
2CHL
бAg
açador
R-C-C-H
Reaction
Baeyer's roagent (Test of unsaturation)
(EAR)
Maracutiorul
Hall H.30.
-CH=R-CH=CH.
+ R-G-OH
(EAR) HO
oxidation
R-CH-O-
H
BH THE
R-CH=C-
KMnO/H"
LOOT
R-C-OH
(EAR)
Bir Br R-C-CH
Combustion
204,/ca. (Test of unsaturation
(EAR)
Br Br
(n-10
+00+H0+
H-C=C-HN R-CEC-H R-CEC-R/
20
W
OH
Hoa
→ R-CEN
R-CH-CHI,
NANH
CHINI
Pd/ (Reduction)
R-CEON
IOS
DDOCOUNT GLANCHI
ch) R-CH=CH-R
HP:
Gico, Pazt a
Aral ANO
Amo Cuci (for larminal Alkyne)
R-CECA
White ppt) R-CEO
Rad pril
H-CEC-H
a, MG HHH-TEC- H
ни
Манн, Barch reduction (Partial Reduction
tiram R-CH=CH-R +
H
(ler lerminal Alkyne)
ral Alky) +R-SCMBT-RH
Chlore
CHAPTER
Chemistry HandBook
HYDROCARBON - BENZENE
PREPARATION
Nooh-00- decarboxylation
Red
CH
GUCH OH or PO,
BENZENE
H:HOVE
NH
REACTIONS
Electrophilic Substitution Reactions
XVIII
Autumn loni
CH-CD GT Rale
Nitrition
NOS HNO, + H2SO.
Reduction
H
So.
HSD
Birch Reduction
ADMISI
or H 30.-30.
Bale Tridal cralt ll CH2
CLUV.
LHC+0.
Abywion
ara
CH
+A10.
CHI -- CH,
ICH t-0) CHQ-CHACH,
No reactions
Fridal croll
Mayon
COOH
Cartelle |
co
0, Zy11,0
CHO 3 CHO Ozonolysis
ko
AC
kolla
4504C
Ala,
0.V.O. 250-C
H,0
Po dut
600 + 3H,0
001, Aud AG
CHAPTER
Chemistry Handbook
HALOALKANE
NoBruHSO.
PCL.
HC-CH, OH H,C-CH-OH
HI
POL
TV DIY S6
HP04 NES
Ca. a viy
H.C-CH=CH.
lalylic abitubon
Red P+B
Soal: CH. --
X
CH, CH,-X SOCl2 AR-X
(X-FCI, Br. 1)
Preparation Preparation
HB
CH=CH,
Nol Aggtone
HC-CH-CH
Hazra. Lues Regen
| |-ITT-BT11
HBE
TEBR
cel,
H.C-CH-CH
H.C-CH-CH,
Peroxide
z--
Hã
BT/BOOK
CH CHCC.
HỌC-CH=CH,
H.C-CH-CH:
CH-CH=CH,
NBS cal
Br/ca, H.C-CH-CH-Br
Br
0-2
Nucleophilic abstitution
S_1 3251 S 2 - 152-3
(X=FCI, Br, D
8
With | PH cho H
H
-CH-
, 4 ha
Dkho
+H;0-CH-OH A KOH MATAD
Rare
SOHC-CH >
DOCE
REACTIONS
LEH + H2=CH- =
H,
CHI HC-
achch Corey
1.C-C-N 0 HC-CH, CC-H4 Hat BN:
HC-TH H - LAI TU am
0,70H Orno IX
.
AN =
H.C-CHANEL
YETLO
CH HIEU
-R10/14-0, HC-CH-D
H_C=CH.
ALL NCH
.
MONO , H,C-
Ho-H-S1 + Mall
HC-01N
MO
CH, O-cẠI, CHỊ CHỐNG
He-01-S-CH,
|T
CHI, H
ALS
H 1
.
mas
-
M
an RUDOCH
PHYSICAL PROPERTIES
Ma Paling point: R->R-BrR-CR-F16) Density: D-CH-CK (1) pole
moment CH -C1-CH-FXCH-B>CHAL 12 Bord enthalphs.CH-F-CH.C H, BCH
TRI-HALO ALKANE
HUDOTYKA
il
OH CH-C-R or H_C-CH-H
(Haloların test)
HC-C-CH,
Preparation
a.c-e-H
a, N:OH
0. or Noci
O=C +HCI Light
CI Csod.
HNO,
→ CI,C-NO, who
CLINIC
+ CH. NEC (Test of Primary amine)
Reaction
cc.
For
CH,
HALO-ARENE Cand HNO + Canc HS.
(ESR)
C/FeCl, (ESR)
HE
СНО ACT,
PHI. Na 11,0
(ESA)
Fit Resson
CH.E
60
2000. 6. 2010
NIVEO
Wur-Fit Recto
AIC,
(ESRT
A
-F1 6-N
họ NH
NH,
ASN
da=0
ECI, LTD GH H 3
(ESR
FOH
chloro diptum
trichloroethed
11 NC), 620K 200 am
InH
CEN
NAI
N-OH Conc. H SO
or
moon
(NSH)
NET
warm
(ESR)
NO,
-0-NO
SO.H
B) Bong Doll
ICT Maltis point
(A
Reactivity toward Nudloophile
HOCH,
$8.00
.
No.
NO
NO,
121
CHAPTER
Chemistry HandBook
ENER
A
LLY
GRIGNARD REAGENT
REACTION
GRIGNARD REAGENT as Nucleophile
R-E-O-H
R-C-OE: Maxinexcess/H0+
R-C-R
но
0
(19 R-CH=-H
H-C-H Ho
REC-a
leg, mox
R-C-R
OH
O-H
(2) R-CH-CH,
HC-c-H
HO
REC=0 NaX in excess/H 0
+ R-CER
0-0-02
0-H
R-C-R
R-C-R HO:
RECEN HD
R-C-R
OH
H=C=OE:
H-C-R
R-CH-CH
lea
HO
RMgBr
OSBE
OH
R-CH-R –
=
H-C
R
H-C-0 FM Acce
R-CH=CH, HMax ин он
R-CH-CHER
R-C-R
R-O-H
HO
O-H R-CAR
R-e-01
Teq. u 0
C-OE:
OE: HO
0-H
d-c-CH KMTRESS/H30
+ R-C-R
R
Ra
d=(-d
R-C
obce
C-CEN
+ R-CEN+Msa
decea
R-C-R
CINH.
+R-NH, 4MG
GRIGNARD REAGENT as BASE (Active H-containing compound)
MGOHBr + RH
H-O-H
H-N-R
| |-
-
R-H
MORBr + R-H+
R-O-H
HEN-R
D-O-D
NR
Mg(OD Br +R-D
(RMgBr
R-H+Mg.
HAB BC
PHACO
D M9Br +R-H
R-CEC-H
R-
HR-ceCMOB
MINH.Be+R-H
H=H.
e
.Rufus
L
Chemistry HandBook
ALLENDE
ALCOHOL
DI HSO
EAR)
Pd+H of LAH/N.BH
H0
CH, BCH
CH-CHO.
GMP
HoloadHO
NOBHL
Pd+H, or LLAIH./NIBH,
H0
CH-CACH
CH=CH,
LAH./NBH.
CH
CH=CH,
BH IHF HO/NOH
HOS AE NAR)
Reduction
LAH, S AE NARCH-C-OH
CH-CHO
HO
RMX (NAR) N HO
Ingrid Zymas
LAH
HO SAE NARCH,-G-OCH.
CH 0,+H0
WOTOSU
H
(CHẠC CH=CH, HONOHACH- (CH..C_CHECHBHUTHF
НОН
CH,OH
CH=CH,
Reagent
MH
1н, -нно
CCPDCA
CHECH,
HO
Grignard
w
ISNI
H=CH-CH,
+ CH-CH=CH-OH
OH + CH-CH-CH-CH,
CH-CH,
Phy
2 H.C-C-CH
(NSRO
0
K Cro MOH pneu Reaga
CH-CH=CH-CH
HONAR)
H.0"
Sucea borche et de
pe mah. MB, la nars
ОН
Eu 500°C
CH, CH INARI CH, CH
CH,
ОН RCH-CCHCHC CHE
SAE
CH-C-o (SAE)
O/60°C
+2CH,OH -2/H,0
ОН 1-C- CH CH MBT CH=C-CH;
NAR CH. MBr
CH
(AR)
LH-CO-H,C-C-
H LCH-B. AK CH-OH
SAE
Evo Mg dryi
COM
H.C=CH-CH,
OH
HO
NAR)
Chemistry Handbook
ALCOHOL
PC.
(NSR) Na
poa,+CH-CH.-G
CH CH-ONa+
rouldtion
Acid baco
CH MgBrCH+CH.CH OB]
HPO 43CH, CH-C14
PB:
(SAB CH OOH.CH--0-H:-H.
HPO,+30H - CH.-B
Conc. H.SO.
Reduction
H0450,-CH-CH. a. soa: ô SO,+CH, CH, G, SOC
HO-H2-HD
Aline CH-CH2
HTC
KVH PO
NETH)
CH-CLD SAD
40 CH=CH,
HC/Znaci
- CH CHẤT Lucas Reset
HB: Ör CHH-Br NaBr + H SO, BR-O-HA
NH ,CH, CH, NHỮ ALO, ALO.
LH THI 620 K Ellerination
Na == CH -0-CH-CH CH, CHI 11.
H
5 / 140 C
-CH=CH-0 CH
CH-CH,
CH=CH
Conc. HSO.
170C
CHCHHSO,
HSO 100°C
DEHYDROGENATIONS
OH H.C-CH-CH:CH, H,C-CH-CH-CH,
2 Alcohol 1° Alcohol
CH HCC-OH
CH Aloha!
leagent
No reaction
H.C-CH-CH-0-OH
HCC OH+CH,C-OH
-CH,
CH, HC-C=CH,
CH, CHC-CH,
w500°C
1500"C
H.C-CH-CH=C-H
Immediately
Lucas Reagent HCIZNCL
within five min. Coudiness appear upon heating after 30 mins.
VICTOR MAYER'S TEST
-C-CH,
CH
H-CH TH
H.C-¢-1
HC-CH=CH-I:
PL,
CH, CH-CH-CH
CH, HC-CH=CH-NO,
(CH.).C-NO
CH-CH, CH,-NO, HC-CH-C-NO,
H.C-CH-C-NO,
No reaction - Colourless
INO,
ration)
ERE
Chemistry HandBook
Reactions
GMP
ETHER
| C,
H SO, 1000
H,C-CH-o-da-CH,
W
2C HOH amcn corinuous cheticason!
(NSR) IS 21
The Cool
HCI
CH-CHH
CHAD -
HC-CH-ON meron synthesis (SR-X - Allume
(NSR) IS, 21
HC-CH-O-CH-CH, HC-CH-O-CH,
R-O-R
Hi/cold
HHBr-HO CH, CHI + CH, CH, OH
Zisel Method
BEA
2CH)
Dry A3,0
[NSHI
2CH]
EN EF
HVS
NOS
PHENOL
GMP
SO.Na
NaOH
H.C-C-H
(1) H
000. (ii) H /
HO THICH CUCH)
HO
16-2
MgBr
O/Air Oxidation
НО Industrial method
0./60°C/A H,O/H
PHENOL
COOH
OH
NH+CHUA
TO V205 300°C
HOS
OCH,
OCH,
Olof win
A
Er in CHODOH
O
CHCO,
S
discos. O
Promination
O
COCH
Frede
r
eaction
Aloha dren
cenic. HSO. con HNO
Inkrat
WEDGE
-
Chemistry HandBook
PHENOL
Fions
Reactions
Q-CH
Hc-c-a
5-
C-CH,
1200 Barengen
ОНІ
NH,
Zogu
Tia
H, OH
PHENOL
PO
Ph-0),PO Word
GCH=
Precea
O-N
NOH
--Th.
huu
VE
Schatten Baumann Reaction
Cem KOHSO.
Door
24,6 Trophenol
NO.
H SO
NEO
Green
50
1250
NOH
Kalbi Soudt Hention
OH
SO H
2000
ET E e como
mon moon
CH-
Hitter NOH
Bakal polyke
CH OH
NAOH
но
е
Image
CO NO.
1250
oid integree
Org-o mere
OH O
Nero,
H, 90,
consent
CO ΑΝΟΗ
1250A
"OH PLOH
them to be
PHOHACO РОС,
Phenyl salicylate
—
127
Chemistry HandBook
CHAPI
B
ALLY
Comparision
of S,1 and 8,2
Comparision
of E, and E.
12
Bi B
KRX KRX Rate
Rate KRIN:)
Stereochanistry No special
C|Stereochemistry Racerisation | Ігмеsian
geometry
Substrate 3° > 2°>>>1° 3° >2 1 D Substate 3>
2°>1>Mex Mex >1>2>3
(reactivity)
Needs
God TG Lerving Group Need Good LG Neats Good LG
LG Rearrangement Possible
Not
Possible H Rearrangement possible No Posable Summary of
S1, S2, E, and E, Reactions Order of reactivity of
Rok: Mechanism
Soluant
OH.CH;8
Low
(CH2), có
High
Reactioity order towards SD
Solvent
Low) Polar apronc
S, I or S 2 and E, or E, Solvent
High
R-> R-Br > R-Cl > R-F SNI
Solvent
Low
*
S. 2 - Sierit ni
Polar aprotic
(E1)
Protic
T
Primery (1)
| Secondary (2)
Tatimy (3)
E2
TOGGLE.CHANDIGAR
Mexily Slat low T masty El at high i
128
CHAFTEN
Chemistry HandBook
Preparation of Aldehyde & Ketone both
R-OH-KCIOVH SO.
39. KOHRCH.CHCI,
(1929)
HSO,
R-OH -_PCC
RC=CH
(1°,29)
order JB
BH THE
RCHO RCOR
ROACH
300°C
Н,ОЛОН
(1927
ripamar
HIO,
2(RCOO),Ca
2 >19 Strong
R-CH-CH-R
ОН ОН R-CH=CH-R
bes
Mno
300-C
2RCOOH
ity not
HOYZn
pot
Good
Possible
RCN
H.O
cod Ar-CH, HO (Etard reduction)
DIBAL-HE
H.O
RCOOR
athy
Ar-CH
RCHO ArCHO
HO
co+HA_ O
-H l . RCOC
Baso, Roser und Reduction)
Snaha RCN - (Stephen's Reduction) (u) H.O
aniwyd AICI, (Gattoman Koch aldehyde synthesis)
HN-HC anhyd Alch, Getterman aldehyde synthesisi
irds E,
R-F f strong i at ortho:
RCN —
RCN
RMX НО
RCOR AFCOR
R COC annyd. AICI,
R.COCO
CHAPTEN
Chemistry HandBook
Reaction of Aldehyde & ketone
ОН
HCN HCN . (NAR)
- HOEVOH
CON
MATH
CH-OH
LIAH
of NBH OT N+CH OH
анрун
ОН COOH OH
LAH,
woll kishter
NH,
HCHO
H.NL
CH
reduction
reduction
NHÉ,
+
MOHA
OH/A
Ry=0
H
SO Na Elulphite compound while crystalline
2n-Ha Ha
Ckmensions rediebon
/
Ric=0
ROHA
*
VUA ROH/H. VOR
OR
OR Hentaceta
Hotel
OR
RPA
(0H
PR
Alechai
Reaction of only Ketone
CHO
Chloreload
CH, CHILE
CH. CH,
Mg-Hg
RO
101CH.COOH+HCOOH.CO.UH,0
Aldot Reaction (Aldehyde or ketone walth H (0) 2CH,CHO
Aquadil NOH
TH=CH-CH-CH,-CHO HACH-CH=CH-CHO
LH
Alde condensation product) AHA
CH, dil Moh
FREE
Cannizzard reaction (Aldehyde with no H) 2HCHO con NaOH, CH,OH-HCOONa
= TESTS
WWDGGER4100
Chemistry HandBook
CARBOXYLIC ACID
HO
HoH
C--a.
те ги
HyC-CH-OH_RC1,021
KMio и Е,
Preparation
11.0
H.C-CH-C-OH
0
HC-C-NH -
1
CHI,
[Halolommtes
HO"
O=C=0/H0
H.C-C-0.
HOW
H.C-C-OENOH
- CH.MgBr
or NAOH
Reactions
KHE
NILA
H0+00,+RCOONa+
UN SOC.
HC-80
H-C
1.C-C-0> E-C-OH>P.40-OHRI-C-OH
HN,
H.C-NH2
LAHHH
S
.C-CHOH
evid H.SO,
H.O
CI 0 HC-C-C-OH
Here
Hei Volha Zinky Recom
TEST
PHC-CH-C-OH
.6"
Cote HNO,Conch
1 KMnO, KOHA
(2) H
R[172. Ako CHCCC, L, H,CHICO CÚCH, gul
No reaction
-
Fadolat tent
to continue
BFeBr
EVOCA
B Fem
132
Chemistry Handbook
Ο Η ΑΡΤΕΗ
-
ALLEN
AMINES PREPARATION
7, 0
R
H,C-CH-X
-N=C=0
NH (Excess
-HX JAminolysts]
HOVH,0
Gabriel Phthalmidd Synthesis
har et HC-&-web
Bra KOH HLO, HO
[] NH, (11) KOH,CH, (iii) H.O. H
-N
Holmen . BETI4ld.
2 Degradation
[NERỊ
NocHol/EIOH
R-CENTINORIATHEL_0
CHÍNH RCH NHL
R-NH,
HN,, H,80,
Schindi
HN,,H.SO.
H,O
R-C-OH Created
Reactia
HO
Fe/HC or H/PdR-NO,
R-NC
or Sr/HCI or SnCl+HCI
CNH,
R-CH=N-OH LAH/EOor Ne/ELOH
H/N
-R-MgX
REACTION
R-NH; C,
HỌ
СНС, КОН
-
=N-R
TEST
R.NH(2)
ol
Reagent
R-NH (10)
R.N(3)
Ph-so,a Hinsberg reagent)
R-N-SO, Ph
H soluble
NaOH
RN-S-Ph
No reaction
NaOH
7
IR-N-50,-Ph]Nat
-NH-SO-Ph
Insoluble
A/Hga, Mustard oil test
R-NH-C-SH
Hga R-NEC-S+HOS
R N-C-SH
Hga, a
No reaction
KOH, Ph-N=CS
No reaction
134
Chemistry HandBook
EAAL
ANILINE PREPARATION
42
O=0
S1/HCI or Fe/HCI
Reduction
NINJA HO!
LITER mida
atban
NH, ZC 300C
CHNHI.
3-5 BrMg
0EC-NH.
-
=
=
Br./KOH Holmagn Bromonide
Degradation
REACTION
Br/HO or Br/cs
[_x316320
Organisasi
NHCOCH,
NHCOCH, NH,
(CH-0),
HNO HSON
OH or
(Group Protection)
NOU
NH,
NH,
NH,
VYNO.
Corc HNO, Conc.H.SO.
Base
Scholam
Re-furs
C-a
Nu 9
HC-C-a WINO,+H SO,74,07
(Group Proleçiku
DÉPh |
NH,
NH,
nic
CHCI,
(1) Conc H SO, 2453473K
21453-473K O
N
S+H9S
KOH Carbylamine Test
SOH
eso,
Fredd crafts reagent. No reactions
Chemistry Handbook
MALLEY
BENZENE DIAZONIUM CHLORIDE
REACTION
Cu/HCI
rosa Dos
uope
Gallerman
NHL,
(-NH
CW/HBE
Coupling reaction
H -vHC-N-ONE
-Nha
CH,OH/A or H.PO:/8
H.C
OH
N.NO/HC0-50
HD/H"
YNEN
283K
Cuci/HCI
KI
NENCI
Br
HBE
GB, HB
Sandmeyer reaction
LIÊN HN
HBF
N.NO
Cu.
FISR
Free Radical Substitution reaction
FIER FIER
ассир карагандароо
м
1136
CHAPTER
Chemistry Handbook
Nutshell review & preview of ORGANIC REAGENTS
10. CCI + OH- (Reimer Tiemann) 1.
Alcoholic KOH
R-X Alkene ; Elimination
OH
-00 + product
+ p-Product
2. Aluminium Ethoxide
RCH-O — R-C-0-CHR (Tischenko Reaction)
CO + HCI + AICI,
(Aldehyde)
(Exte)
8-6
+ p Product
Aqueous KOH/NaOH R-X → ROH Nucleophilic substitution reaction also used for Cannizzaro
reaction with aldehyde.
Gatterman koch reaction
12. HCN + HCI + AICI, O
Gaiterman Aldehyde Synthesis
4. Baeyer's Reagent (Alkaline cold dilute KMnO)
RCH=CHR' = RCH-CHR'
OH OH
Syn) alkene
- 1. 2 diol (used to detect unsaturation)
00,+ p-Product
00+ p-Product
26. H
7. Cu CL + NH0H
Used to Detect Terminal Alkyne Red Precipitate observed
Kobe's reaction 15. CHƯA
17. DMSO
138
Polar aprotic solvent: favour S 2 me
UT S2 mechanist
ALLEN
Chemistry HandBook
t
Fe+ Br_FeBr,
o
mt
28. H (Ni) can reduce
6) R-C-
R R.CHOHE OLD
G) R-C-H
RCH OH
Fehling solution
ed to identify – CH=O group. PHCHO gives -ve test Observation: red ppt of Cu O
formed
(i) RCN RCH,NH; -CC
HC=CH- --CH, CH -
-CH-CH
Grignard Reagent Follows (t) Acid base reaction (ü) NAR (1) NSR
29. H.Pd/BaSOJ
Quinoline R-C-CIRCHEO
25. H.SOJA
RCH-CH=RCH=CH,
OH Saytzeff product: C+ mechanism Rearranged alkene can be formed
34. NaHCO,
RCO,H_NHCO...RCO;Na + čo,
35. NaHSO,
OH
R-C-R
soNa
26. HNO, (NaNO, + HCT)
(1) RNH, R-OH (H) PINH + PhN : (0 - 5°C (H) PhNH PHOH (high temperature)
White crystals, soluble in water used to separate carbonyl from noncarbonyl compound]
OH
CN =Ó
PH
0-
00
36. NaOH(aq)
Chemistry HandBook
MALLY
48. Na In Liq. NH, (Birch reduction)
RH R-CECRC =C
37. Ninhydrin
Detection of amino acid Observation : Purple coloured ton
58. ROH
59. Snci
38. NaOR
Strong base : C) RCH-CH-R-RCH=CH-R
(trans alkane) 49. Oso, + H2O
RCH=CHR=RCH-CHER
on addition) OH OH
Saytzel Produd
Esclmitation
R
R-CH=CH-
ZA + DADO
-CHO-R-CHD
HO VZN
(Oromolysts proce!
Ichaban condensation
Woene
RM9X RCH-CH2-OH
39. NaOH + x, or NaOX
G) R-C-NH,
RNH, Hoffman Degradation)
61. Silver
Br_CC
62. Agor
40. NaOH + Cao
RCO H → RH
53. P(red) + Br,
6) CHCO,H - H,C-CO,H (HVZ reaction
63. SOCI
() ROH →R-BI
41. MO/300 C
used for -CO, & -H.O in carboxylic acid. 42. NBS
0-0
46. Zn(Hg) + HCI [Clemmensen's reduction]
R-C-R-R-CH-R
57. RCOCI + AICI, Friedel craft acylation)
47. NH, -NH/OH- Wok Kishinz reduction)
R-CO-
R R-CH-R 140
0-08
VE
Η ATE HY
LEWE
ALLEN
Chemistry HandBook
ROH+
RICOH 790, R=COR
0
(Esterification reaction)
Enter formed
64. Tollens Reagent Test
(i) Terminal alkyne gives (ii) Aldehyde Group gives (iii) Ketone gives ve test (iv) c-hydroxy Ketone gives
(v) HCOOH gives (vi) Hemi acetal gives (vii) PhNH-OH gives
SACI + HCI
R N=N=R'
RNH, + RNH
65. Benzene sulphonyl chloride
It is used to distinguish and separate (Hinsberg reagent) 1.2 and 3 amines,
i) RCN → RCH=0 [Stephen reduction]
- НО
ocess!
Sn + HCI
66. Tetra ethyl lead (TEL)
67. v.0.
1) RCN + R-CH, NH,
$1. Silver salt RCOOAg (Hunsdiecker reaction)
Br./CCI/
D
Malec anhydride!
VUE
ОН
ction)
43. SOCI,
R-G-OH/R-OH-R-C-a/R-C
IMPORTANT NOTES
gen
tioni
Chemistry Handbook
Nutshell review & preview of ORGANIC NAME
REACTIONS
• Aldol Condensation
CECH.
CECH, ---H-C-CH=CH ECH,
Bay!
HC-CE: H
--C-C-OCH
C-CH, -510-C-CH=6-ch,
EID=-LH
Claisen Condensation
H.C-E-ON.
Perkin Condensation
condenados
=C-C-OH
Cinnamach
Benzoin Condensadon
• Haloform Reactlon
Pinac rearr
y todos Olyan 20
en mc-*-*i Mate HC &-risk CHI, E-COM * 01 «R-Ratu
Chefe
Cloures can
Carbylamine Test
HCI
OH H
Relmer Temman Reaction
CHCL. ΚΟΗ
(Salicylic acid
(Salicylaldehyde)
O-H
OH 0
R-&-**, * **,$0,
Curtius Reaeffan
---C1 IN PR -NH.
AHD 44,0
-NH,
Gabrie
Schimdt Reaction
НА,
next to
ul-014>Ex=-=-&-ox5.204 cm
142
LLEN
ALLE
y
Chania Renatuak
Chemistry HandBook
S-CH,
mo
DFC-C-00-H
prad u "
+H.C
mandato" uc-do-
Bayer villiger oxidation
C-OCH
0-0-H
CH-CH-CH, CHICCH,
CHIP
1-OH
O=0.0.com
Cumeme hydroperoxide
-
Pinocol-Pincolone rewtangement
M-o-o
-
a
O-R(+M)
COOH
0-R(+M) OR -OH DON, WO
Birch Reduction
NH,
lịm NH.
RH
R-C=C-R
Nad CC NHR
R
-CEC-H ENHAdd bene radion
1_Na -R-CECN
| Dato'
Gabriel Synthesis
-C-OH
H.O.
TH Q-OH
+CH, -OH
? ALLEN
CHAFTER
Chemistry HandBook
NAME REACTIONS
Reagent
Product
Nane
Reactant
Zn-Hg conc. Ha
Akane
Clemmensen Reduction
Aldehyde & Ketone
NaOH (phenol) HC (Aniline)
888
Azo Dye (Detection of OH or NH ..
Coupling Reaction
NaNo, + HCI
0° -5°C
sand
Dlazotzatlon
COCI/CS
Erard reaction
Lê nadelideri
Dipheny!
Halo benene
Na Dry ether
Flitlg Readion
Anhydrous Ala,
АДhyl Benzene
Rosenmund reduction
add chlonde
aldehyde
Sabala-Senderens rectlon
H. PdBaso boiling xylene Raney N/H, 200300 C
Unsaturated hydrocarbon
Akane
Sandmeger readion
CH, N,
CUCI/HC or CuBdHBr or
CUCN KCN heat
Halo or cyanobenen
Gatteritain Reaction
CHN, 1
CuHX(HEHC||
Halobendene
Schotten-Baumann reaction
berzolytated product
(phend or aniline a akohol)
NaOH + CHCO3
Loco -Acco
Stephen reaction
alkyl cyanide
Willantson synthesis
Aldehyde
alkyl halde
Wurtz-Fittig readlon
m) SnCWHCI (1) H.O sodium alkoxide of sodium phenoxide
Na/dry ether
Elhe
kyl halide + ayl halide
144
-
akul benene
Chemistry HandBook
Η ΑΡΤΕ Η
ALLE
POLYMERS
ADDITION POLYMERS
S.No
Name of Polumer
Nature of Polymer
Starting Materials 1. Polyolefins
CH=CH
Polyethylene or Polyethene
Low density homopolyne
(branched chain grouth Homopolymer, linear,chain growth Homopolymer,
linear.chain growth
Homopolymer, dan growth
Copolymer chain growth
2.
Polypropylene or Polypropene
CHHH, Polystyrene
CHCHCH
H0-&
-LOH
Copolymer, step growth, linear
Homopolymer,
linear
CARBOHYDRATES
Carbodydrates are defined as optically active polyhydroxy aldehydes or ketones
or the compound which produce such units on hydrolysis. Monosaccharide
(CH,0) Esingle unit, can't be hydrolysed: Glucose and fructose. Oligosaccharides
gives two to ten monosaccharides on hydrolysis. Disaccharides (by glycosydic
linkage)
Mutarotation: When either form of D-glucose te placed in aq. solution it slowly
form the other via open chain aldehyde and gradual change in specific
OH
ΟΗ Η OHN
HOCH ин HOH
H,C-OH
OH
O
H
OR
Acetal
Henled YOR
OR
21.41.4 Glycosidie H
OH linkage) fa-D-glucose)
Two c-D-Glucose unit Lactose: но cң,
HO-CH HOOD
Example
Sucose
ОН Heriketal
H OH D-DGalacios
| |--Clients (1.4 Glycosidic linkage)
Chemistry HandBook
Starch: Am Amylase:
arch: (Amylose & Amylopectin) colose : (Straight Chain) :
нс-он
H.C-OH
CH, OH H HOH
e is via cific ned
OH HA
OH
IZ
(0-1,4 Glycosidic linkage) Soluble in H O & gives blue colour with l.
Amylopectin (Branch chain) : (CH,,0).
due rewieric
H.C-OH
H .C-OH = OH HO H
r in
HOT EH O Diaslace CH, O, maltose) nH_0 -maltase 2CHOga-D Glucose
HO
HO-CH. 1,6-Glycosidic linkage
x
3.5 km
- OH
H
Cellulose THU, nC,H,206 B-D-Glucose
2011
Lo
OH
1.4-Glycosidic linkaje
ITE
СНО
SW
5Acci