Professional Documents
Culture Documents
O 1. Lewis Base
R H
O
2. Nucleophiles H H
3. Polar protic solvents
CH3CHCH3+H
+ CH CHCH 3
3
Difference between alcohol & phenol
OH O+
H H
OH CH2OH
O
IR
Phenol alcohol H+ H H
partial double bond character between C & O (a)
.S
CH2 CH2 OH
1 alcohol
(primary alcohol)
CH3CHCH3
2 alcohol
(Secondary alcohol) Ans.
OH
OH
(a) (b) (c) OH
CH3 H
CHCOH
3 Oxymercuration Demercuration (O M D M)
CH3 O OH
1. Hg(OAC)2 H H
.J
3 alcohol CH3 CH = CH2 CH3CHCH3
(tertiary alcohol) 2. NaBH4
(n hexane or paraffin solvent)
CH2 = CH OH (vinylic alcohol)
Features:
CH2 = CH CH2 OH (allylic alcohol)
(1) Markownikoff addition
(2) No. Rearrangement
General Methods of preparation
(3) Non classical carbocation
N
O
(1) from alkanes 1. Hg(OAC)2 H H
(1) OH
Cl2 /h aq.KOH 2. NaBH4
CH4 CH3 Cl H
CH3 OH
Me Me O
1. Hg(OAC)2 R H
Br2 /h (2) OR
MeCH MeCBr 2. NaBD4 D
Me Me CH3
CH3 O
O 1. Hg(OAC)2 H H
(3) CH3CCH = CH2
H H CH3COH 2. NaBH4
CH3
CH3 CH3 OH
CH3C CH CH3
(2) from alkenes
OH CH3
+ O
H H H CH3CHCH3
(i) CH3 CH = CH2
1
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
CH3 OH
(5) Conversion of lower alcohol into higher alcohol
Ans. (3) CH3C CH CH3
IR
2. H H OH
2.H /HOH
1. B2H6 THF O
2.
OO H RCH CH OH
2. H H OH 2 2
5.
.S
CH3 CH = CH2
2.CH3 COOD
1.B2D6 / THF
CH3 CH = CH2
H
H
NaNO2
R N:
HCl
R N2 Cl
(diazotisation)
2.CH3 COOD
H
1.B2H6 / THF
6. CH3 CH = CH2
2.CH3 COOH Mechanism:
Ans. 1.
OH H H
(1) H (2) H (3) D + + +
.J
:
:
OH OH
(4) CH 3CHCH 2 (5) CH3CHCH2 H
H D D D H
(6) CH3CHCH2 +H
RN = NO RN = NOH
D H H +
N
aq.KOH R OH O + RN = N D RN N
RX H +
SN2 (8) from Carbonyl compounds
aq.KOH H
CH Cl R
2 H2 /Hi
C=O R C OH
O R Na/EtOH
H H R
CH2Cl
Sn/HCl
(4) from grignard reagent
Zn/ ACOH
2 R mg 1. O2
2 R OH
2.H /H2O Fe/H2O
Mechanism:
. . LiAlH4
R
:
R + O = O ROO
(9) MPV Reduction:
2
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
CH3 O
1. CHO Al R
R CH3 3
CH3 (6) R H+ CH3MgBr CH4 + RO
MgBr
C=O CH OH + Al(OH)3 + 3 C = O
2. H3O+
R R CH3 (7)
O
: :
(10) Oppenaur Oxidation O
H H
CH2 = C = O CH2 = C O CH3 C OR
R (CH3 )3 COAl R
CH OH 3. C=O + OR
R R H
O
(11) from Carboxylic acid
C R'OH/H OR
LiAlH4 (8) R OH R CH (acetal)
R COOH R CH2OH
OR
O O
(12) from Carboxylic acid derivatives
O C R'OH C O
(9) R H R OR + H H
LiAlH4
IR
(a) R C Cl R CH2OH
O
LiAlH4 Reaction due to C O bond Cleavage
(b) R C OR R CH2OH
ROH
O O
C C LiAlH4 (1) HI
R OH RH
(c) R O R R CH2OH Red P
O
(d)
.S LiAlH4
R C NH 2 R CH2NH2 (2) R OH
1 2
HCl/ ZnCl
2 R Cl.(Lucas Test)
SN or SN
(13) from hydrolysis of ester.
SOCl2
O (3) R OH R Cl + HCl + SO2
O SN1
C H2SO4 (dil)
(a) R OR R C OH + ROH PCl3
(4) 3R OH 3 R Cl + H3PO3
O O SN2
dil H2SO4 18
(b) C CH3 C OH+ MeOH O PCl5
.J
Me OMe (5) R H R Cl + HCl +
18 SN1 & SN2
O
General Reaction of alcohols
(a) Reactions sue to O H bond Cleavage P
Cl Cl
ROH Cl
(6) Conc.H2SO4 CH CH = CH
CH3CH2 CH 3 2
N
O | 170C
Na RO Na+ + H
(1) R H 2 OH
1
(acidic nature) (E1CB) Conc. H2SO4(E )
OH
ThO2 170C
O
(2) R H + Blue litmus Red litmus
(Alcohols are weak acids)
O
(3) R H + NaOH
Oxidation of alcohol
O O
(4) R H + NaHCO3
Red hot
1. R1 CH R2 R1 C R2
Cu Tube
O O OH
(5) R H + CH2N2 R CH3
3
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
O CH2OH
Red hot K MnO4
R CH OH RC Q.2
Cu Tube H H
H
(1 alcohol to aldehydes)
K MnO4 /H
O Q.3 OH
Red hot
R CH CH3 R C CH3
Cu Tube
OH O
(2 alcohol to ketones) O
CH3 CH
CH3 Ans. 1. 2. 3.
Red hot
R CH CH3 R C = CH2
Cu Tube
OH
:
(3 alcohol dehydration to alkenes)
N
/CrO3/HCl
IR
(3) P.C.C.
Ph CH OH Red hot Cu
Q.1
2 1: 2 : 3
OH 1 aldehyde
CH 2 ketone
CH3 Red hot Cu
Q.2 .S 3 no.effect)
Red hot Cu OH O
Q.3
1.
P.C.C.
OH
O O
Ans. 1. CH C
OH P.C.C. H
2.
O
.J
:
CCH3 N
2. 3.
4. Collins Reagent : CrO3 : CH2Cl2
Oxidation of alcohol OH O
+ +
(2) Oxidising agent KMnO4 / H or K2Cr2O7/H P.C.C.
O 1.
K MnO4 /H
N
1. R CH2 OH RC
H O
(1 alcohol acid)
C
K MnO4 /H OH P.C.C. H
2. R1 CH R2 R CR 2.
1 2
4
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
Ans.
MnO2 Ph
CH2 OH O
Q.1 Me C OH + Ph C OH
O
Ph
CH O
Q.2 H C OCH3
O Ph O
Me
Q.1
Me C O C Ph H
Q.3 Et C O CH
H2O Me
Ph O
Q.4 Me C O CH2 CH3
O
O
H
Q.2 H C OH + CH3 OH
IR
CH3OH CO
O Q.5
Me H
Q.3 Et C OH + CH OH CO
Me
O O
H O
Q.4 Me C OH + CH2 CH3
OH Q.6 R O C R
Q.5
.S O
COH
+
HO
H
Q.7
OH O
COMe
COH
HO
O OH O
O
C
Q.6 R OH + HOCR H
OPh
Q.8
OH O
.J
C Me O
OH H
Q.7 + Me OH
COMe
Q.9 H
(Methyl Salicylate)
OH Et
CH3
N
O
COOH O
Q.8 + Ph H H
Q.10 MeCO H
(Phenyl Salicylate ) Me
Me
MeOH
Q.9 H COOH +
H
Et
CH3
O
H
H
Q.10 Me C OH + HO
Et
5
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
Cl
: :
Phenol:- OH NaOH
2.
OH OH
OH NO2
+ H O H
3. N2 Cl
IR
OH NaOH/CaO
4.
OH
(Soda lime decarboxylation)
OH OH 5. Hydroperoxide Method:-
Catechol Resorchinol Quinol (hydroquinone)
CH3 H3PO4
+ CH2 = CH CH3 ------
CH3
.S
OH
CH3
O2/air
H /H2O
OH OH -------- + ------- ----------
O-cresol m-cresol p-cresol
H2SO4 /(conc.)
6. --------------
.J
Reaction of Phenol:-
(1) Electrophilic aromatic Substitution:-
N
OH
Phenanthrene
HNO3
(a) ----------- + -----------
Methods of preparation:- H2SO4
1. Dows Prcess:-
Cl OH
NaOH Br2
(b) ----------- + -------------
360C/320atm CS2
Br2
(c) ---------------------
H2O
6
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
OH COOH O
CH3 C
OH
NaNO2 + O ----- + ------
(d) -------------------- CH3 C
HCl
O
OH
Phenol as Nucleophile:-
: :
Conc.H2SO4 OH
(e)
------- + ------------
O
: :
(f) Reimer Tiemern Reaction:- O
OH 1. Ph H + C6H5 C Cl
O
C6H5 C O Ph + HCl
IR
CHCl3
-------- + --------- O
KOH
CH3 C
: :
O
2. Ph H + O
(g) Kolbe Reaction
CH3 C
OH
O
O O
NaOH
.S
1. CO2 (high P)
--------------- Ph O C CH3 + CH3 C OH
---------------
2. H
(h) Fries Rearrangement:- Hydrogenation:-
O OH
OCCH3
H2 /Ni
.J
---------------
AlCl3
------ + ------------
Reduction:-
OH
(i) HO + N=N -----
+ Zn/dust ---------------
N
Coupling Reaction:-
(j) Leaderer marnase reaction:- Oxidation:-
OH OH
O
C
H H / H+ CrO3
---------------
---------------
OH OH (Quinone)
CH2 CH2 CH 2
CH2 CH2
B alkaline polymer
7
----------------------------------------------------------------------------------------------------
ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
R
SI
J.
N.
8
----------------------------------------------------------------------------------------------------
IIT-JEE ChEmistry by N.J. sir
A-833, Indra VIhar, near IL back door,
ContaCt: 9414969800, 9549908816
web : symmetryiitjee.com