ALCOHAL & ETHER Page # 27

Exercise - III Subjective Level-I

MCQ : 5. Which of the following reaction esterification ?
1. Compound which gives alcohol on reduction (A) EtOH + Acetic anhydride 
is/are (When reacts with LiAH4) H
(B) EtOH + CH3CO2H 
(A) Me– C –Cl (B) Me– C –NH2 
|| || O
O O ||
(C) EtOH – CH3– C –Cl
O O (D) None
|| ||
(C) Me– CH–CH2 (D) Me– C –O C –Me C H2/Pd/BaSO4
CH3C CH3l
6. CH3– CH–CH2 (X) (Y) (Z)
O
2. Which of following compound undergo acidic O
hydrolysis. Identify X, Y, Z :

O (A) Y is CH3– CH  CH2C  CCH3

|| |
(A) CH3–CN (B) CH3– C –O–Et O  CH3
(B) Y is CH3–CH2 CHC  CCH3
O O O |
|| || || CCH3
(C) CH3– C –Cl (D) CH3– C –O– C –CH3
(C) Z is CH3– CH  CH2  CH=CH–CH5
|
3. Which can be cleaved by HIO4 ? O  CH3
O O (D) X is CH3– CHCH2C  CCH3
|| || |
(A) CH3CH2 C CH2 C CH3
O
OH O
| || 7. Which is/are corect statement ?
(B) CH3 CH CCH2CH3 CH3 CH3
CH3/OH
(A) C C
H2SO4
H O CH3
(C)
nucleophile attacts here when epoxy linkage is cleaved

OH OH CH3 CH3
O O NaOH
|| || (B) C C
(D) CH3 CCH2 CHCH2 CCH3 CH 3OH
| H O CH 3
OH
nucleophile attacts here when epoxy linkage is cleaved
4. Which of the following alcohol can not be (C) This is only affected in reduciton to 2º alcohol
oxidized by KMnO4 :
O
OH
(A) (B) OH NaBH4

OH O CH 3OH

O
(C) OH (D)
O
+
H
(D) R– R–C–OH+H–O–R

These bonds undergo cleavage in the reaction

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com
 Page # 28 ALCOHAL & ETHER

8. 3-methyl-3-hexanol can be prepared by - 12. Which one of the following alcohols can be
(A) CH 3Mgl and 3-hexanone, followed by oxidised by K2CrO4 ?
hydrolysis (A) Ethanol (B) Tert butyl alcohol
(B) C2H5 Mgl and 2-Pentanone, followd by (C) Isopropyl alcohol (D) Allyl alcohol
hydrolysis
(C) C3H7Mgl and 2-butananone, followd by 13. Asparmatge, an artificial sweetener is a peptide
hydrolysis and has the following structure. Which of the
(D) C 4H 9 Mgl and propanon, followed by following is correct about the molecule ?
hydrolysis O
C6H5
9. PBr OH
OH  3 (X) O

H2N NH
CH 3 O O
(i) CH3–CH–CHO CH3
Mg / Et O
  2  (Y) +
(Z) (A) It has four functional groups
(ii) H2O
(B) It has three functional groups
(C) on hydrolysis it produces only one amino
(A) X is Br
acid
(D) on hydrolysis it produces a mixture of amino
acids
(B) Y is MgBr

OH CH3 Comprehansion : (Q.14 to Q.16) :

Aldehydes and ketones react with oine
(C) Z is C—C—CH3 molecule of analcohol to form compounds called
hemiacetals, in which there is one hydroyl group
H H
and one either-like group. Reaction of a
H CH3 hemiacetal with a second molecule of alcohol
gives an acetal and a molecule of water. We
(D) Z is C—C—CH3 study this reaction
H O–H
ROH OH ROH OR
O + +
CH=CH–CH–CH3 H OR H OR
KMnO4/  SOCl2 A hemiacetal An acetal
X+Y The carbonyl
H H OH (has an–CH and (has two–OR
10. group of an
aldehyde or ketone an–OR group to groups to the
the same carbon) same carbon)
D OH
Identify the product X and Y. Draw structural formulas for the hemicetal and
O acetal formed from these reagents. The
|| stoichiometry of each reaction is given in the
(A) X is Cl– C – C –CH2Cl problem.
||
+
O H (P)
(A) O+2CH3CH 2OH
COCl
Cyclohexanone Ethanol
(B) X is
+
H (R)
D O (B) O+HOCH2CH2OH
D O Cyclohexanone Ethylene glycol

CH2–C–Cl
(C) Y is

D O
(D) Y is ClCO– C –CH3
||
O

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com
 ALCOHAL & ETHER Page # 29

OH O O
H+
+ (Q) (C) (D)
(C) O
Acetone
OH
cis-1,2-Cyclohexanediol
16. Product R is -

14. Product P is - O
OEt OEt O O
(A) (B) OEt (A) (B)
O
OEt
OMe OMe
(C) OPr (D)
(C) (D)
OPr

15. Product Q is -

O
(A) (B)
O

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com