1252 Alcohol, Phenol and Ethers

O
ONa OCOONa
CH 2 CH 2 (c) (d)
1. CH 3  CH  CH 3  A 
 B 
 C
PBr3 Mg
|
OH COOH
8. Reaction
  D Here, D is
H 2O
[BVP 2004]
OH
(a) CH 3  CH  O  CH 2  CH 3 OH OH
| acid or base CH 2 OH
CH 3  CH 2 O 
(b) CH 3  O  CH  CH 2 CH 3
|
CH 3 CH 2 OH
is called [MP PET 2003]
(c) CH 3  CH  CH 2 CH 2 OH
| (a) Lederer Manasse reaction
CH 3 (b) Claisen condensation
(d) CH 3  CH 2  CH  CH 2 OH (c) Benzoin condensation
|
(d) Etard reaction
CH 3
9. When phenol is reacted with CHCl 3 and NaOH followed by
2. Phenol is more acidic than [Pb. CET 2003]
acidification, salicyldehyde is obtained. Which of the following
OH OH species are involved in the above mentioned reaction as inter
mediate [DCE 2000]
OCH 3

(a) (b)
O O
(a) H (b) CHCl 2
NO 2
CCl 3
(c) C2 H 2 (d) Both (a) and (c) O
H
3. In the reaction, C6 H 5 CHO  (CH 3 CO )2 O  ( A)
CH 3 COONa
(c) (d) All of these
CHCl
product (A) is [Pb. CET 2000] |
(a) Acetaldehyde (b) Cinnamic acid OH
10. The order of solubility of alkanols in water is
(c) -nephthol (d) Phenol
(a) Propanol < Butanol > Pentanol
4. The correct order of ease of dehydration of following is
[CPMT 2004]
(b) Propanol > Butanol > Pentanol
(c) Propanol > Butanol < Pentanol
OH OH OH (d) Propanol = Butanol = Pentanol
11. In the following compounds
I II III
(a) I > II > III (b) III > II > I OH OH OH OH
(c) I > III > II (d) III > I > II
5. PCl5 reacts with a compound containing [Pb. CET 2002]
(a) SO 3 group (b) – OH group NO 2
(c)  NO 3 group (d) – NO group CH 3
NO 2

(I) (II) (III) (IV)

6. Cumene process is the most important commercial method for the The order of acidity is [IIT-JEE 1996]
manufacture of phenol. Cumene is [KCET 2004] (a) III  IV  I  II (b) I  IV  III  II
(a) 1-methyl ethyl benzene (b) Ethyl benzene (c) II  I  III  IV (d) IV  III  I  II
(c) Vinyl benzene (d) Propyl benzene 12. Butanal with dilute NaOH gives [UPSEAT 2000]
7. The compound X in the reaction [Roorkee 1999] OH
|
ONa OH (a) CH 3 CH 2 CH 2 CCH 2 CH 2 CH 2 CH 2 CHO
|
+ CO   X 
390 K
2

HCl
H
COOH
is O
||
COONa ONa (b) CH 3 CH 2 CH 2 C CH 2 CH 2 CH 2 CHO
(a) (b)
(c) OHCCH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CHO
COONa
 Alcohol, Phenol and Ethers 1253

OH
|
(c) (d)
(d) CH 3 CH 2 CH 2 C  CHCHO
| |
H CH 2 16. Fittig's reaction produces
|
(a) Alkane (b) Alcohol
CH 3
(c) Diphenyl (d) Diethyl ether
13. The correct order of the solubility of the different alcohols in water
is [Pune CET 1998] 17. p-cresol reacts with chloroform in alkaline medium to give the
(a) n-propyl alcohol > ethyl alcohol > n-butyl alcohol compound A which adds hydrogen cyanide to form, the compound
(b) Ethyl alcohol > n-butyl alcohol > n-propyl alcohol B. The latter on acidic hydrolysis gives chiral carboxylic acid. The
(c) n-butyl alcohol > n-propyl alcohol > ethyl alcohol structure of the carboxylic acid is
(d) Ethanol > n-propanol > n-butyl alcohol [AIEEE 2005]
14. Which one of the following will most readily be dehydrated in acidic
condition [IIT-JEE (Screening) 2000]
CH 3
CH 3

(a) CH(OH)COOH (b)

O OH OH
CH(OH)COOH
(a) (b) OH OH

O OH CH 3
CH 3

(c) CH COOH
2 (d)
(c) (d)
CH COOH
2

OH OH OH OH
15. Which of the following compounds will be most easily attacked by
an electrophile [CBSE PMT 1998, 99]

Cl
(a) (b)

OH CH 3

(SET -26)

CH 3  CH  CH 3   CH 3  CH  CH 3 

3 PBr Mg
1. (c) The reaction sequence is as follows
| |
OH Br
2 propanol [ A]
 1254 Alcohol, Phenol and Ethers
CH 3 O OH CHO
| | |
CH 3  CH  MgBr 
CH 2  CH 2 CH 3 CH 2 CH 2  C  CH  CH 2  CH 3
|
[ B]
H
(CH 3 )2 CH .CH 2 CH 2 OMgBr   (CH 3 ) 2 CH .CH 2 CH 2 OH
H 2O

[C ]  Mg (OH )Br
[ D]
isopentylalcohol
13. (d) Ethanol > n-propanol > n-butyl alcohol
or 3 methyl butcane 2-ol Solubility of alcohols in water decreases as the size of alkyl
2. (d) Methoxy group due to +I effect increase electron density on OH group increases because tendency to form hydrogen bonding
– group, thus making it less acidic. Thus o-methoxy phenol and decreases.
acetylene are less acidic than phenol, p-nitrophenol is more 14. (a) Aldols (-hydroxy aldehydes or -hydroxy ketones) readily
acidic than phenol undergo dehydration to form , -unsaturated aldehydes or
3. (b) Perkin reaction is the condensation reaction in which an ketones.
aromatic aldehyde is heated with an aromatic aldehyde is +
heated with an anhydride of an aliphatic acid in presence of O OH O OH 2
O
sodium salt of same acid to form ,  unsaturated acid.
+
H
+
–H , –H2O
C6 H 5 CHO  (CH 3 CO )2 O 
3

CH COONa
-Hydroxy ketone H H
Benzaldehyde acetic anhydride 15. (c) Phenol is most easily attacked by an electrophile because
presence of –OH group increases electron density at o- and p-
C 6 H 5 CH  CHCOOH  CH 3 COOH positions.
cinnamic acid acetic acid
4. (b) The correct order of stability of carbocation is as follows 16. (c) 2C6 H 5 Cl  2 Na  C6 H 5  C6 H 5  2 NaCl
Dry
ether diphenyl

CH 3
CH 3
CH 3

OH OH OH
17. (b)
III II I
 
CHCl 3

OH
 
HCN
 OH
CHCl CHO
5. (b) PCl5 is used in organic chemistry to replace the –OH group 
2

OH O O
by –Cl and carbonylic oxygen by (Cl 2 ) . A
CH CH O – OH CH 3 CH 3
3 3
|

CH C – (CH ) 3 2 CH  

H 3O

CH(OH)CN CH(OH)COOH
6. (a) CH


O2 
CO OH OH
  
3
H 2O / H
+
catalyst CH 3

Cumene or 1, Phenol Acetone

methyl ethyl
benzene
ONa ONa OH

7. (b) + CO 2  
390 K
COOH
 
HCl
COOH
HCl

It is Kolbe’s reaction.
8. (a) It is Lederer Manasse reaction.

***
OH O OH
CHCl CHO
9. (b) –HCl
2
–H2O
+CHCl +NaOH 3

Intermediate Salicyldehyde
10. (b) Propanol > Butanol> Pentanol
The solubility of alcohols in water decreases as the molecular
mass increases. As the size of alkyl group increases,
hydrophobic character increases, Hence solubility decreases.
11. (d) IV > III > I > II.
 NO 2 group is electron withdrawing group while CH 3
group is electron releasing group.
12. (d) 2CH 3  CH 2  CH 2  CHO  dil. NaOH 