Professional Documents
Culture Documents
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) -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
ðod for the &anufacture of "henol' Cu&ene is [KCET
2004]
(a) 1-ðyl 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
+ +
ol & 2 ca#e $ehyl b% 3 or
lcohol iso+e#yla
) *
2 2 2 3
( ) (
D
OH CH CH CH CH
24. (d) 4etho,y grou" due to 5I effect increase electron
density on OH > grou", thus &aking it less acidic'
4rs' )=900D E(/890 9%%91W90 : (4)98"8108983
OH O-CH
3
OH
OH
+
H
O H
2
+
H
carboniu& ion
OH
!hus o-ðo,y "henol and acetylene are less acidic
than "henol, p-nitro"henol is &ore acidic than "henol
25. (b) .erkin reaction is the condensation reaction in which
an aro&atic aldehyde is heated with an aro&atic
aldehyde is heated with an anhydride of an ali"hatic
acid in "resence of sodiu& salt of sa&e acid to for&
, unsaturated acid'
+
COONa CH
O CO CH CHO H C
3
a#hydride aceic
2 3
de ,e#-aldehy
5 6
) (
acid aceic
3
acid ci##a$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 (-hydro,y aldehydes or -hydro,y ketones)
readily undergo dehydration to for& , -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,
ðyl 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
-=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