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ALCOHOL , PHENOL & ETHER

1. Which will undergo a Friedel-Craft's alkylation reaction
[Pb. PMT 1998]
(a) 1, 2 and 4 (b) 1 and
(c) 2 and 4 (d) 1 and 2
2. !he "roduct #A$ in the following reaction is
A
O
CH C H
RMgI
  → 
2 2

[MP PMT 2003]
(a) RCHOHR (b)
3
CH RCHOH ⋅
(c)
OH CH CH R − − −
2 2
(d)
OH CHCH
R
R
2
3. %lycerol boils at
C
o
290
with slight deco&"osition'
(&"ure glycerine can be "urified by [CPMT 1983, 94]
(a) )tea& distillation (b) )i&"le distillation
(c) *acuu& distillation (d) +,traction with a
sol-ent
4. .henol D C B
NaOH O H SO H NaNO
   →    →       → 
2 4 2 2
/
/a&e of the abo-e reaction is [KCET 2003]
(a) 0ieber&ann$s reaction
(b) .hthalein fusion test
(c) 1ei&er-!ie&ann reaction
(d) )chottenf-2au&ann reaction
5. !he correct order of boiling "oint for "ri&ary ), 1 (
o
secondary ) 2 (
o
and tertiary ) 3 (
o
alcohols is
[CPMT 1999; RPMT 2002]
(a)
o o o
3 2 1 > >
(b)
o o o
1 2 3 > >
(c)
o o o
3 1 2 > >
(d)
o o o
1 3 2 > >
6. What will be the "roducts of reaction if &etho,yben3ene
reacts with HI
(a) 4ethyl alcohol (&ethanol) 5 iodoben3ene
(b) 4ethyl iodide (iodo&ethane) 5 ben3ene
(c) 4ethyle iodide 5 "henol
(d) 4ethyl iodide 5 iodoben3ene
7. +thylene reacts with 2aeyer's reagent to gi-e [CPMT 1988]
(a) +thane (b) +thyl alcohol
(c) +thylene glycol (d) /one of these
8. Which of the following state&ents is correct regarding
case of dehydration in alcohols
[CPMT 1980, 85; MP PMT 2001; BHU 2002]
(a) .ri&ary 6 )econdary (b) )econdary 6 !ertiary
(c) !ertiary 6 .ri&ary (d) /one of these
9. 7,iran is
(a) +thylene o,ide (b) 8iethyl ether
(c) +thyl glycolate (d) %lycolic ester
10. .ro"an-1-ol can be "re"ared fro& "ro"ene by alcohol
[AIIM 2003]
(a)
4 2 2
/ SO H O H
(b)
O H OAc Hg
2 2
/ ) (
followed by
4
NaBH

(c)
6 2
H B
followed by
2 2
O H

(d)
4 2 2 3
/ SO H H CO CH
11. 8istinction between "ri&ary, secondary and tertiary
alcohol is done by [MP PMT!PET 1988; RPMT 2000]
(a) 7,idation &ethod
(b) 0ucas test
(c) *ictor 4eyer &ethod
(d) 9ll of these
12. 7,idation of which of the following by air in "resence of
-anadiu& "ento,ide gi-es "henol
(a) !oluene (b) 2en3ene
(c) 2en3aldehyde (d) .henyl acetic acid
13. !he &ost suitable &ethod of the se"aration of a 1 : 1
&i,ture of ortho and para nitro"henols is
[CBE PMT 1994, 99; CPMT 199"]
(a) 8istillation (b) )ubli&ation
(c) Crystalli3ation (d) Chro&atogra"hy
14. Which of the following does not for& "henol or
"heno,ide
[A#MC 2000]
(a)
Cl H C
5 6
(b)
COOH H C
5 6
(c)
Cl N H C
2 5 6
(d)
Na SO H C
3 5 6
15. Which of the following will be obtained by kee"ing ether
in contact with air for a long ti&e [RPMT 2003]
(a)
OH O CH CH O H C − − − − ) (
3 5 2
(b)
OH OCH H C − −
2 5 2
(c)
OH H C O H C
5 2 5 2
− −
(d)
OH O CH CH O CH − − − ) (
3 3
16. When a &i,ture of ethanol and &ethanol is heated in the
"resence of concentrated
4 2
SO H
the resulting organic
"roduct or "roducts is;are [M$%&'$( MEE 1995]
(a)
5 2 3
H OC CH
(b)
3 3
OCH CH
and
5 2 5 2
H OC H C
(c)
5 2 3
H OC CH
and
3 3
OCH CH
(d)
,
5 2 3
H OC CH

3 3
OCH CH
and
5 2 5 2
H OC H C
17. (n the following grou"s
I
OAc −
II
OMe −
III
2
Me OSO −
IV
3 2
CF OSO −
!he order of lea-ing grou" ability is [IIT 199"]
(a) ( 6 (( 6 ((( 6 (*
(b) (* 6 ((( 6 ( 6 ((
(c) ((( 6 (( 6 ( 6 (*
(d) (( 6 ((( 6 (* 6 (
18. +"o,ides are
(a) Cyclic ethers
2
NO
CH

1
CH
2
CH

2
COOH

OH
4
ALCOHOL , PHENOL & ETHER
(b) /ot ethers
(c) 9ryl-alkyl ethers
(d) +thers with another functional grou"
19. !he reaction of
CH CH CH =
3
OH
with HBr gi-es [IIT)*EE 1998]
(a)
2 3
CHBrCH CH
OH
(b)
CHBr CH CH
2 3
OH
(c)
2 3
CHBrCH CH
Br
(d)
CHBr CH CH
2 3
Br
20. Which of the following co&"ounds on boiling with
4
KMnO
(alk') and subse<uent acidification will not gi-e
ben3oic acid [KCET 2001]
(a) 2en3yl alcohol (b) 9ceto"henone
(c) 9nisole (d) !oluene
21. !he best reagent to con-ert "ent--en-2-ol into "ent--in-
2-one is [AIEEE 2005]
(a) 9cidic "er&anganate
(b) 9cidic dichro&ate
(c) Chro&ic anhydride in glacial acetic acid
(d) .yridiniu& chloro-chro&ate
22. When alcohol reacts with concentrated
4 2
SO H
inter&ediate co&"ound for&ed is [A#MC 2005]
(a) Carboniu& ion (b) 9lko,y ion
(c) 9lkyl hydrogen sul"hate (d) /one of these
23.
C B A CH
OH
H C CH
O
CH CH Mg PBr
    →   →    →  − −

2 2 3
3
|
3

D
O H
  → 
2
=ere, D is [B+P 2004]
(a)
3 2
3
|
3
CH CH O
CH
H C CH − − − −
(b)
3 2
3
|
3
CH CH
CH
H C O CH − − −
(c)
OH CH CH
CH
H C CH
2 2
3
|
3
− −
(d)
OH CH
CH
H C CH CH
2
3
|
2 3
− − −
24. .henol is &ore acidic than [Pb. CET 2003]
(a) (b)
(c)
2 2
H C
(d) 2oth (a) and (c)
25. (n the reaction,
) ( ) (
3
2 3 5 6
A O CO CH CHO H C
COONa CH
    →  +
"roduct (A) is [Pb. CET 2000]
(a) 9cetaldehyde (b) Cinna&ic acid
(c) β-ne"hthol (d) .henol
26. !he correct order of ease of dehydration of following is
[CPMT 2004]
(a) ( 6 (( 6 ((( (b) ((( 6 (( 6 (
(c) ( 6 ((( 6 (( (d) ((( 6 ( 6 ((
27.
5
PCl reacts with a co&"ound containing [Pb. CET 2002]
(a)
3
SO −
grou" (b) > OH grou"
(c)
3
NO −
grou" (d) > NO grou"
28. Cu&ene "rocess is the &ost i&"ortant co&&ercial
&ethod for the &anufacture of "henol' Cu&ene is [KCET
2004]
(a) 1-&ethyl ethyl ben3ene (b) +thyl ben3ene
(c) *inyl ben3ene (d) .ro"yl ben3ene
29. !he co&"ound X in the reaction [R,,-.// 1999]
is
(a) (b)
(c) (d)
30. 1eaction
OH
OCH

NO
2
OH
(
OH
((
OH
(((
OH
ONa OH
COOH
5 CO
2
X
COONa ONa
COONa
ONa
COO
H
OCOON
a
ALCOHOL , PHENOL & ETHER
OH CH
OH
OH CH
OH
O CH
OH
2
2
or base acid
2
+ +
is called [MP PET 2003]
(a) 0ederer 4anasse reaction
(b) Claisen condensation
(c) 2en3oin condensation
(d) +tard reaction
31. When "henol is reacted with
3
CHCl
and NaOH
followed by acidification, salicyldehyde is obtained'
Which of the following s"ecies are in-ol-ed in the abo-e
&entioned reaction as inter &ediate [0CE 2000]
(a) (b)
(c) (d) 9ll of these
32. !he order of solubility of alkanols in water is
(a) .ro"anol ? 2utanol 6 .entanol
(b) .ro"anol 6 2utanol 6 .entanol
(c) .ro"anol 6 2utanol ? .entanol
(d) .ro"anol @ 2utanol @ .entanol
33. (n the following co&"ounds
!he order of acidity is [IIT)*EE 1991]
(a) II I IV III > > > (b) II III IV I > > >
(c) IV III I II > > > (d) II I III IV > > >
34. 2utanal with dilute NaOH gi-es [UPEAT 2000]
(a)
CHO CH CH CH
OH
H
CCH CH CH CH
2 2 2
|
|
2 2 2 3
(b)
CHO CH CH
O
CH C CH CH CH
2 2
||
2 2 2 3
(c)
CHO CH CH CH CH CH OHCCH
2 2 2 2 2 2
(d)
3
|
2
|
|
|
2 2 3
CH
CH
CHCHO
OH
H
C CH CH CH −
35. !he correct order of the solubility of the different
alcohols in water is [P2%/ CET 1998]
(a) n-"ro"yl alcohol 6 ethyl alcohol 6 n-butyl alcohol
(b) +thyl alcohol 6 n-butyl alcohol 6 n-"ro"yl alcohol
(c) n-butyl alcohol 6 n-"ro"yl alcohol 6 ethyl alcohol
(d) +thanol 6 n-"ro"anol 6 n-butyl alcohol
36. Which one of the following will &ost readily be
dehydrated in acidic condition [IIT)*EE 34-//%&%56 2000]
(a) (b)
(c) (d)
37. Which of the following co&"ounds will be &ost easily
attacked by an electro"hile [CBE PMT 1998, 99]
(a) (b)
(c) (d)
38. Fittig's reaction "roduces
(a) 9lkane (b) 9lcohol
(c) 8i"henyl (d) 8iethyl ether
39. "-cresol reacts with chlorofor& in alkaline &ediu& to
gi-e the co&"ound 9 which adds hydrogen cyanide to
for&, the co&"ound 2' !he latter on acidic hydrolysis
gi-es chiral carbo,ylic acid' !he structure of the
carbo,ylic acid is
[AIEEE 2005]
(a) (b)
O
H
O
O
H
O
H
O O
H
O
H
O
3
CCl
H
O
2
CHCl
OH
CHCl
|
O
H
OH
(()
CH

OH
(((
)
2
NO
OH
(((()
NO
2
OH
((*
)
Cl
CH

OH
OH
CH

CH(OH)COOH
OH
CH

CH(OH)COOH
OH
CH

CH
2
COOH
OH
CH

CH
2
COOH
ALCOHOL , PHENOL & ETHER
(c) (d)
1. (c) or will undergoes a Friedel Craft$s
alkylation on ortho or "ara "osition because of &ore
electron density'
2. (c)
  →  − − → + =
HOH
R CH
OMgI
H C RMgI CH CH
2 2
|
2 2

OH CH CH R OH MgI − − − +
2 2
) (
3. (c) !he li<uids which deco&"ose at its boiling "oint can
be "urified by -acuu& distillation' %lycerol which
deco&"oses at its boiling "oint (>ABK) can be
distilled without deco&"osition at 4AK under 12mm
Hg "ressure'
4. (a) 0ieber&ann$s reaction'
5. (a)
o
1
alcohol
o
2 >
alcohol
o
3 >
alcohol
2oiling "oint of alcohols decreases as the nu&ber of
branches increases'
1. (c)
I CH HI
3
+ → +
". (c)
→ + + = O H KMnO CH CH
2 4 2 2
4 2 3
KOH KMnO
OH CH
OH CH
2 2 3
2
Glycol
|
2
2
+ +


8. (c) Correct order of dehydration in alcohols C 6 2C 6 1C'
9. (a) 7,iran is ethylene o,ide,
O
CH CH
2 2

10. (c)    →  + = −
2 2
6 2 2 3
6
O H
H B CH CH CH
OH CH CH CH
2 2 3
− −
11. (d) 8istinction between "ri&ary, secondary and tertiary
alcohol is done by all three &ethods : o,idation,
*ictor&eyer and 0ucas test'
12. (b)
5 2
2
air ,
O V
O
   → 
13. (a) o- and p-nitro"henols are se"arated by stea&
distillation because o-nitro"henol is stea& -olatile
while p-iso&er is not'
14. (b) 2en3oic acid'
15. (a)    →  − −
ligh /
2
!
O
R O R
OH O CH CH O H C − − − − ) (
3 5 2
11. (d)
3 3
) (
3 3
4 2
OCH CH OH CH OH CH
Conc SO H
     →  +
5 2 3
) (
5 2 3
4 2
H OC CH OH H C OH CH
Conc SO H
     →  +
5 2 5 2
) (
5 2 5 2
4 2
H OC H C OH H C OH H C
Conc SO H
     →  +
1". (b) (* 6 ((( 6 ( 6 (('
18. (a) Cyclic ethers are called e"o,ides'
O
CH CH
2 2

19. (b)
CH CH CH = −
3
  → 
HBr

Br
CH CH CH
|
2 3
− −
20. (c)
3
OCH on
4
KMnO
o,idation does not gi-e
ben3oic acid'
21. (c) Chro&ic anhydride in glacial acetic acid is the best
reagent to con-ert "en--en-2-ol into "ent--in-2-one'
22. (a)
− − −
|
|
|
|
OH
C
H
C

− − −
+
|
2
|
|
alcohol
"roo#aed
|
OH
C
H
C
− − −
|
|
|
|
C
H
C

− = −
| |
C C
I# all cases i#er$ediae is carbo#i%$ io#,
a#d here $ay be 1, 2&hydride or 1, 2&$ehyl
shi' o 'or$ $ore sable carbo#i%$ io#(
23. (c) !he reaction se<uence is as follows
  →  − −   →  − −
Mg
A
PBr
CH
Br
H C CH CH
OH
H C CH
) *
3
|
3
+ro+a#ol 2
3
|
3
3
    →  − −

O
CH CH
B
MgBr
CH
H C CH
2 2
) *
3
|
3
Br OH Mg
O H
C
OMgBr CH CH CH CH
) (
) *
2 2 2 3
2
( ) (

  → 
ol & 2 ca#e $ehyl b% 3 or
lcohol iso+e#yla
) *
2 2 2 3
( ) (
D
OH CH CH CH CH
24. (d) 4etho,y grou" due to 5I effect increase electron
density on OH > grou", thus &aking it less acidic'
4rs' )=900D E(/890 9%%91W90 : (4)98"8108983
OH O-CH
3
OH
OH
+
H
O H
2

+
− H
carboniu& ion
OH
!hus o-&etho,y "henol and acetylene are less acidic
than "henol, p-nitro"henol is &ore acidic than "henol
25. (b) .erkin reaction is the condensation reaction in which
an aro&atic aldehyde is heated with an aro&atic
aldehyde is heated with an anhydride of an ali"hatic
acid in "resence of sodiu& salt of sa&e acid to for&
α, β unsaturated acid'
    →  +
COONa CH
O CO CH CHO H C
3
a#hydride aceic
2 3
de ,e#-aldehy
5 6
) (
acid aceic
3
acid ci##a$ic
5 6
COOH CH CHCOOH CH H C + =

21. (b) !he correct order of stability of carbocation is as
follows
2". (b)
5
PCl
is used in organic che&istry to re"lace the >
OH grou" by >Cl and carbonylic o,ygen by
) (
2
Cl −
'
28. (a)
29. (b) 5
HCl
K
CO    → 
390
2
  → 
HCl
(t is Folbe$s reaction'
30. (a) (t is 0ederer 4anasse reaction'
31. (b)
32. (b) .ro"anol 6 2utanol6 .entanol
.he sol%biliy o' alcohols i# /aer
decreases as he $olec%lar $ass i#creases( 0s
he si-e o' al1yl gro%+ i#creases, hydro+hobic
characer i#creases, 2e#ce sol%biliy decreases(
33. (d) (* 6 ((( 6 ( 6 (('
2
NO −
grou" is electron withdrawing grou" while
3
CH −
grou" is electron releasing grou"'
34. (d)
→ + − − − NaOH CHO CH CH CH dil( 2
2 2 3
3 2
| |
|
2 2 3
CH CH
CHO
H C
OH
H
C CH CH CH − − − −
35. (d) +thanol 6 n-"ro"anol 6 n-butyl alcohol
)olubility of alcohols in water decreases as the si3e of
alkyl grou" increases because tendency to for&
hydrogen bonding decreases'
31. (a) 9ldols (β-hydro,y aldehydes or β-hydro,y ketones)
readily undergo dehydration to for& α, β-unsaturated
aldehydes or ketones'
3". (c) .henol is &ost easily attacked by an electro"hile
because "resence of >OH grou" increases electron
density at o- and p- "ositions'
38. (c)
NaCl H C H C Na Cl H C 2 2 2
di+he#yl
5 6 5 6
eher
3ry
5 6
+ −   →  +
39. (b)
4rs' )=900D E(/890 9%%91W90 : (4)98"8108983
OH
((
(
OH
((
OH
(
CH
O > OH
G
C – (CH

)
2
CH

CH

Cu&ene or 1,
&ethyl ethyl
ben3ene
caalys
2
 → 
O
    → 
+
H O H /
2
CH
5
CH

CH

CO
.henol 9cetone
ONa
COOH
ONa
COOH
OH
O OH O
H
H
OH
2
5
H
5
–H
5
, >H
2
O
O
β-=ydro,y ketone
OH
CH

O
CH

CHCl
2 −
O
CH

CHO

9
OH
CHCl
+
   → 
3
  → 
OH
OH
CH

CH(OH)COOH
OH
CH

CH(OH)CN