JEE - CHEMISTRY

ALCOHOL, PHENOL AND ETHER

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Q.10 (3)
EXERCISE-I Primary alcohol produces turbidity with lucas reagent
Q.1 (2) most slowly i.e. Isobutyl alcohol.
Hydroboration oxidation (Industrial preparation of
alcohol) Q.11 (1)

1 Q.12 (3)
3CH 3 CH  CH 2  B2 H 6 
Dry
(CH 3 CH 2 CH 3 )3 B
2 ether

PBr
(CH3 CH 2 CH3 )3 B 
H2O2
 3CH3 CH 2 CH 2  OH CH3CH2OH 
3
CH3CH2Br
(A)


Q.2 (2)
Alc. KOH
Q.3 (1)
Br2
Q.4 (4) CH2–CH2  CH2=CH2
Q.5 (4) Br Br (B)
As the surface area and molecular weight increases (C)
solubility decreases. So t-butyl alcohol has least surface
area hence its solubility is highest. Q.13 (2)
Alcohol and Acid react with sodium
Alcohol react with sodium to give H2 gas
Q.6 (3)
Acid react with sodium to give carbonic acid
CH3  CH 2  OH 
Conc. H 2 SO4
 CH 2  CH 2  H 2 O Ether donot react with sodium
o
170 C

Q.7 (2) Q.14 (1)

Tertiary alcohol readily reacts with halogen acid Phenol can’t be converted to benzyl alcohol when
heated with Cu at 300°C

 Q.15 (3)
 
    
 Q.16 (3)

O
Presence of 3 alkyl group increases electron density
on carbon atom. Hence  group is easily CH3–C–OH + CH3–CH2–OH
Acetic Acid Ethanol


removed. After the removal of group carbonium ion is H2SO4 conc.

formed which is most stable O
Q.8 (1) CH3–C–O–CH2CH3
Ester
Q.9 (3)
   Q.17 (3)
 
 

    


 
  Q.18 (3)


OH OH OH OH
CH 2  I CH 2 CH 3
| || |
HI HI
  CH  I   CH   CH  I
|  I 2 | |
CH 3 CH 3 CH 3 Cl

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Q.19 (2) Q.30 (2) Williamson’s synthesis

CH 3  CH 2  ONa  Cl  CH 2  CH 3 
     
     CH 3  CH 2  O  CH 2  CH 3
Q.31 (2)

CH3
|

Q.20 (1) CH 3  C O Na  Cl  CH3 

|
CH3
2, 2 dimethyl sodium ethoxide
Q.21 (3)

Q.22 (3) CH3

|
CH 3  C O CH 3  NaCl
N  N  Cl  H NH 2 |
CH3
Methyl-t butyl ether

H
 N  N NN Q.32 (1)
273K
p  Aminoazobenzene (yellow ppt.) C6 H 6 O   CH 3 I  C 6 Hl5OCH 3  I
NO 2  HCl
Q.33 (2)
Conc. H SO
Q.23 (4) CH3CH 2  OH  HO  CH 2  CH3 
o
2 4

140 C
Q.24 (2)
CH3 CH 2  O  CH 2  CH 3  H 2 O
Q.25 (2) Diethyl ether

Q.34 (1)
OH OH Cyclic ethers are called epoxides.
COOH
+ CCl4  4KOH 
Q.35 (2)
Salicylic acid

Q.36 (3)
+ 4KCl  2H 2 O
CH3–CH2 + C2H5–ONa
Q.26 (1) I


 
  CH3–CH2–O–CH2CH3 +NaI

Example of Nuecleophilic subtitution reaction.

 OH Q.37 (3)

R–X + R–ONa  R–O–R + NaX

p-hydroxy azobenzene
(orange dye)
This is an example of coupling reaction R–O + R–X

It is an example of Biomolecular neucliophilic substitution

Q.27 (4) reaction. i.e. SN2.
Q.28 (2)
Phenol is more acidic than ethyl alcohol Q.38 (1)
Williamson ether systhesis follows SN2 mechanisms. So
Q.29 (2) steric hinderance in halides should be minimum. so
sequence of R–X follows the order.
C 2 H 5 Br  C 2 H 5 ONa 
 NaBr
 C2 H 5  O  C2 H5
Sod. ethaoxide diethyl ether CH3 > 1° > 2° > 3°
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Q.39 (4) Q.5 (2)

  O OH
R  OH  R  X  R O    R    R HOH
CH3 – C – H + CH3 – MgBr CH3 – C – H

 R  O  R  HX CH3

Q.40 (2)
Q.6 (2)
NH2 OH
HNO2 /H
  HOH
CH3 – CH2 CH3 – CH2 CH3 – CH2
–H2O
C2 H5 CH 2 CH 2 OH  MgBr(OH) –N2 ()
(A)
n -butyl alcohol Q.7 (4)
– +
Q.41 (1,4) Due to polar – O – H bond
Q.42 (2)
O – CH3 OH Q.8 (2)
  +CH3I Due to presence of lone pair electron on O-atom

Q.9 (2)
Q.43 (2) Ethers do not form hydrogen bond.

Q.10 (2)
R  O  R  HX 
 RX  R  OH 
HX
 R  X  H 2O
Q.11 (3)

Q.44 (2)  
Q.45 (3)
R – Br + NaOR1 R – O – R1 + NaBr
Q.46 (3) Unsymmetrical
Aromatic and aliphatic alcohols can be distin- ether
guished by FeCl 3 test. Q.12 (3)

1º
EXERCISE-II CH3
CH3 – O – CH – CH3 It have three 1º,
Q.1 (4) 1º 2º 1º and one – 2º carbon
Due to less-effective hydrogen bonding solubility of
Ph – CH2 – CH2 – CH2 – OH becomes minimum.
Q.13 (4)
Reactivity order of alcohol with Lucas reagent 3º > 2º
Q.2 (4)
> 1º alcohol.
1
Acidic nature  Q.14 (4)
pka  value
H OH
Acidity of CH 3  CH  CH 2 OH is minimum due to Conc. H2SO 4
| –C–C– –C=C–
CH 3 –HOH
+I -effect isopropyl group. This reaction involve breaking of ‘C–O’ bond not
‘O–H’ bond.
Q.3 (2)
Due to effective hydrogen bonding boiling point of Q.15 (1)
unbranched alcohol is more than branched chain Reactivity order of alcohols with HCl + ZnCl2 (Lucas
alcohol. Reagent) is 3º > 2º > 1º, because stability of
carbocation of alcohol is 3º > 2º > 1º.
Q.4 (1)
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Q.16 (2) Q.27 (2)

3CH3 – OH + PCl3  3CH3 – Cl + H3PO3 CH3
CH3
CH3 – CH = CH2/AlCl3 CH O2/ CH–O–O–H
CH3
CH
Methylchloride Cumene
hydroperoxide H2SO4/
rearrangement
Q.17 (1)
PCl3, PCl5, SOCl2, HCl can replace –OH group but OH + C
O
not Cl2. Phenol
Acetone
Q.28 (4)
Q.18 (4) Q.29 (1)
Q.30 (3)

R – O – H + Na  R – ONa + 1/2 H2 () [O]/V 2O 5 OH
/200ºC
Q.19 (4)
Dilute acidic KMnO4
Q.31 (3)
OH O
Q.20 (1) OH + Cl — SO2 — Ph

Hinsberg's
reagent

O — SO2 — Ph

Sulphonic ester

Q.32 (3)
OH O¯Na+ O¯Na+ HO
Q.21 (1)
NaOH CO2 COO¯Na+ H+ COOH
OH
(i) BH3–THF/HOH Sodium phenate Salicyclic
CH3 – CH = CH2 CH3 – CH – CH2 acid
(ii) H2O2/NaOH
CH3 1º –Alcohol Q.33 (3)
This is a method of addition of HOH molecule by Reimer-Tiemann reaction
Anti–Markovnikov’s Rule. OH OH OH
CHCl3 + KOH CHO
Q.22 (3) +

Q.23 (1)
CHO
o-salicyldehyde p-salicyldehyde
(Major) (Minor)
Q.24 (2) Q.34 (4)
OH

Benzene nucleus
dil. HNO3 +
    
Q.25 (3)
O–CH 3 Methoxybenzene
(Anisol) [X] [Y]

Q.26 (2)
Steam distillati on
– +     
Due to presence of polar (–O–H) bond phenol
can form hydrogen bond. [Low B.P.due to intramolecular H–Bonding]

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Q.35 (2)
EXERCISE-III
A= ;B= OCOCH3

Q.1 (A,B,C)
Q.36 (1) CH3
NaHCO3 does not give effervescence with phenol.
But ortho-para nitro phenols give effervescence with A CH3MgI + CH3–CH2–C–CH2–CH2–CH3 CH3–CH2–C–CH2–CH2–CH3

NaHCO3. O OH

C2H5
Q.37 (3)
Chlorobenzene has  bond in aromatic ring. B C H MgI
2 5 + CH3–C–CH2–CH2–CH3 CH3–C–CH2–CH2–CH3

O OH
Q.38 (1)
Electron with drawing (–m/–R) nature of –NO2
group increases acidic nature of p-nitrophenol.
C

Q.39 (4)

Q.40 (1)
D

Q.2 (A,B,C)
Q.41 (3)
H–I
R–O–R R – I + HO – R

Q.42 (4)

Q.43 (2)
Decomposition of ether by HI or HBr is called
Ziesel’s method.

Q.44 (2)
CH3 – CH2 – Br + NaOC2H5 C2H5–O–C2H5
Sodium ethoxide Diethylether Q.3 (A,B,C)
(As-Nucleophile)
PBr3 Mg/Et2O
OH Br MgBr
Q.45 (1) CH3

(Williumson’s synthesis) (i) CH3–CH–CHO

CH3

CH3 CH–CH–CH3
CH3
 – + OH
CH3 – C – ONa + Br – CH2 – CH3 CH3 – C – OCH2CH3

CH3 CH3 Q.4 (B,D)

CH3 CH3

CH3 – C – Br + NaOC2H5 CH3– C + HOC2H5
CH3 CH2
3º – alkyl halide

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LiAlH4
OH KMnO4 O CH3–C–NH2 CH3–CH2–NH2

2° alcohal O

OH KMnO4 Not oxidise

LiAlH4
CH3–C–O–C–CH3 CH3–CH2–OH
3° alcohal
Q.5 (A,C,D)
O O

Q.9 (A,B,C,D)

H+/H2O
CH3–C–OEt CH3–C–OH + Et–OH

O O

Q.6 (A,B,D)
– Electrophilic addition reaction.
– Acid catalysed Hydration will give rearrange prod-
uct.
– In cyclohexene reaction occur in either HBO or
oxymercuration – demeruiration or acid catalysed hy-
drolysis product is always cyclohexanol Q.10 (A,C,D)

OH
.
CH3–CH–CH2
O (X)
O

Q.7 (A,C,D)
CH3–I
– Alcohols have –OH group.
O (Y)
– Amide ( –C–NH2 ) does not give alcohol on re- OCH3

duction.
H2/Pd/BaSO4
Q.8 (A,C,D)
LiAlH4
CH2–C–Cl CH3–CH2–OH
OCH3 (Z)

O
LiAlH4 Q.11 (A,B)
CH3–CH–CH2 CH3–CH2–CH2–OH
O

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Q.12 (B,C) Q.23 (A)

Q.24 (D)
(i) CHCl3 NaOH, 
     
(ii) H Q.25 (A)

OH OH Q.26 (C)
CHO
+ Q.27 (C)

(P) CHO Q.28 (B)

(Q)
Q.13 (C,D) Q.29 A  P; B  Q,R; C  S

Q.30 A–P; B–Q; C–R; D–S

(i) CHCl3  KOH
Ph–OH      O OH
(ii) H

A Ni/H2

(Minor) + (Major)

OH O
Q.14 (A,B,C,D)
All above reactions are correct. Reaction A is Koble B P.C.C.

Schmidt, B is Reimer-Tiemann reaction, C protection

of phenolic group at Phenol and D is Laderer-Manase
reaction. OH

Q.15 (A,B,C) H3PO4

C
Q.16 (A,B,C,D)
Q.17 (A,B,C,D)
All reactions are correct. OH Cl

Q.18 (B,C,D) D CON.HCl

Q.19 (B,C,D)
Coupling reaction is shown by benzene diazonium
chloride with more activated ring containining
Q.31 (A) QS (B) S (C) Q (D) P
compounds. Benzaldehyde having deactivated ring.
Q.20 (B)
Q.32 (A) Q, (B) R, (C) S, (D) P

Q.33

Q.21 (B)
Q.34 4 ( III , IV , V , VI )

Q.35 88 gm.
ROH + CH3MgX  CH4 + ROMgX
Let molecular mass of alochol is M
Q.22 (B)
56 0.22
=
22400 M

22400  0.22
M= = 88 gm
56
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Q.36 3

PCl5 NaSH OH
 PhCH2Cl  PhCH2SH  PhCH2S–
CH2–OH  
SN 2 SN 2
PhCH Cl
2 
   CH2–S–CH2
SN 2

Q.37 6
+ CD3 CD3
H2O CD3
+
(a) H   
  Three

 H O
2 H

CH3
D D
(b) H   
  D Three

 H O2 D

Q.38 5
OH
CH3–CH–CH–CH3 H 

–H2O
Ph


+ +

Q.39 78

molecular mass [W] = 234

N = 234/3 = 78

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Q.40 94 length order is: CH3–OH > p-ethoxyphenol (p-EtO-

C6H4-OH)Ph–OH

Sn / HCl
  Q.6 (1)
In (A), extensive inter-molecular H-bonding is possible
while in (B) there is no Inter-molecular H-bonding.

NaNO 2 Q.7 (4)

 
HCl 0 5C

CH 2CH 3
HO CH2CH3
+ H
H+
–H2 O
O O

CH2CH 3

molecular weight of Z = 94

EXERCISE-IV Q.8 (1)

JEE-MAIN O – O
OH /H2 O
PREVIOUS YEAR’S ROH +
Hydrolysis
Q.1 (2)
RO Me Me O
Iodoform reaction can be used for this transformation. Ester

Q.2 (1) So, Ester is unstable in an aqueous basic solution and

undergoes hydrolysis to give alcohol and carboxylate.
Q.3 (4)
Q.9 (4)
First Markownikov's addition one alkene followed by
Ph Ph
EtO K 
EtOH
elimination (X) Major intramolecular Friedel-Craft alkylation takes place
Cl (E 2 )
1. Hg(OAc)2 /H 2O
Q.10 (1)
2. NaBH4 /OH

OH Water Insoluble

(Y) OH 5% HCI
Insoluble
OH
10 % NaOH
Me soluble
m-cresol Me
Q.4 (3) 10 % NaHCO 3
Insoluble
water gas = CO + H2
is also called syn gas because it is used for synthesis of * Oleic acid is also soluble in NaHCO3
methanol.
* o-toluidine is not soluble in NaOH as will as NaHCO3
Q.5 (3)
* Benzamide is also not soluble in NaOH & NaHCO3.
There is not any resonance in CH3–OH. Resonance is
Correct option : (1)
poor in p-Ethoxyphenol than phenol. so C-OH bond
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IV  B.P. 243ºC
Q.11 (2) Q.15 (3)
CH3 CH3  CH3
+

: :
:
OH ONa OCH3  
aq. NaOH CH3I
..O HI/  O
|
–Et-I H
(SN2) OH
Q.12 (4) –CH3OH
S NI
 
COOH I
HO CrO SOCl

3
 

2
 OH I OH
HO
It is nucleophilic substitution reaction.
C=O
O Q.16 (1)
Cl 

 HBr Br– HBr
O OH Br
O
OH HO Br Br
H
Q.17 (3)
Q.13 (1)
CH 3
OH
HI
H 3C – CH 2 – CH – CH2 – O – CH2 – CH 3
Heat
is insoluble in dil. HCl but soluble in NaOH to CH 3

CH 3 – CH2 – CH – CH2 – OH – CH3 CH2 – I

[A]
Ona H 2SO4 /
form
CH 3

CH3 – CH = C – CH3
OH
JEE-ADVANCED
decolorise Br 2 water to give PREVIOUS YEAR’S
Q.1 (A) R,S,T (B) T, (C) P, Q, (D) R

Q.2 (B)
OH
Br Br

Br
(2, 4,6-tribromophenol)
presence
 of dry HCl
 
 RCH 2OH

Q.14 (None) Bonus Q.3 (B)

Order of boiling point of the following compound is
I < IV < II < III
I  B.P 202ºC X 
(1) PBr3 , Bi 2 O
(2) NaI, Mg 2 CO

(3) NaN3 . HCONMe 2
II  B.P. 279ºC
III  B.P. 284ºC All the three reaction are NN2 so X is

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Q.4 (6.00) H – Br 
O – CH3 O – CH3 + Br¯

H2,Pd-BaSO4
Quinoline O + H3C – Br

H
Q.6 (ABC)

Q.7 4

CH2 CH2 Q.8 (C)

C=C
COOH COOH
H H Nitration
conc. (HNO3 + H2SO4)
(P) HO
HO NO2
dil KMnO4(excess)
272 K Directing group
HO
OH OCH3 OCH3
Nitration
conc. (HNO3 + H2SO4) NO2
CH3 (Q) CH3

HO CH2 CH2
O O NO2
OH
C=C C C
O Nitration O
H OH OH H conc. (HNO3 + H2SO4)
Directing group

total 6 – OH group present in a molecule of the major

Q.9 (6)
product.
(C8H10O2)  Gives FeCl3 test means Phenol derivative

Q.5 (D) Rotate plane polarized light means optically active
OH
OH OH
OH
OH

OH

OH
OH OH OH
OH

OH

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