BATCH XII & DROPPER’S 2022 (ADV)

TOPIC ALCOHOL AND ETHER DPP 15B

1. Consider the following reaction. Identify the product:

H 2C CH 2
SOCl 2 Mg O
Pyridine (C2H 5)2 O H
A
O CH2OH

(a) O
(b) O
CH2 CH CH3 CH2 CH2 CH2 OH2
OH

(c) O
(d) O
CH2 CH2 OH2 CH2 CH2 O CH2 CH3
O OH

CH3 I2 / NaOH H 
2. 
A ; A is -
O O O O O
C OH C OH C
OCH3
(a) (b) (c) (d)

3. C7H14O optically active alcohol is oxidized by jones’ reagent to an optically inactive (achiral) ketone.
Which of the following compounds meets these facts ?
OH
(a) (b) OH (c) OH (d)
HO

4. Glycol on treatment with Pl3 mainly gives -

(a) Ethylene (b) Ethylene iodide (c) Ethyl iodide (d) Ethane
5. Ethanol on reaction with acetic anhydride gives
(a) Acetic ester (b) Formic ester (c) Ethaoic acid (d) Acetic ester and Ethanoic acid both
6. A compound ‘X’ with molecular formula C3H8O can be oxidised to a compound ‘Y’ with the molecular
formula C3H6O2, ‘X’ is most likely to be -
(a) Primary alcohol (b) Seconary alcohol (c) Aldehyde (d) Ketone
7. Phenol with Hinsberg’s reagent gives -
(a) Sulphone (b) Sulphanilic acid (c) Sulphonic ester (d) Sulphonal
8. Consider the following reaction. Identify the products A and B:
KHSO 4 LiAlH 4
Glycerol A B


(a) Acrolein, allyl alcohol (b) Glycerl sulphate, acrylic acid

(c) Allyl alcohol, acrolein (d) Only acrolein (B is not formed)
9. Consider the following reaction. Identify the final product C:

(1) NaOH H / H 2O Al 2O 3
Phenol (2) CO 2 / 140°C
A B
CH3COOH / 
C

(a) Salicylaldehyde (b) salicylic acid (d) Phenyl acetate (d) aspirin

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10. Consider the following reaction. Identify the products A and B:

CH3 cold alkaline CrO 3

KMnO 4 A AcOH B

CH3
CH3 CH3 CH3
OH OH OH O
(a) , (b) ,
OH O OH O

CH3 CH3
OH
(c) , (d) no formation of A and B
OH OH

11. Consider the following reaction. Identify the products A and B:

CH3
18
CH 3OH H2O
B H3C C CH2 A
CH3 ONa H
O
CH3 CH3 CH3 CH3

(a) H3C C CH2 , H3C C CH2 (b) H3C C CH2 , H3C C CH2
18 18 18
HO OH HO OCH3 HO OH HO OCH3
CH3 CH3 CH3 CH3
(c) H3C C CH2 , H3C C CH2 (d) H3C C CH2 , H3C C CH2
18 18 18 18 18
HO OH HO OH HO OH MeO OH
12. Consider the following reactions.
CH CH2

P Q R
CH2CH2OH CHCH3 C H2CH3

OH OH

Select schemes P, Q, R out of -

I. acid catalysed hydration II. HBO III. Oxymercuration-demercuraton
(a) I in all cases (b) I, II, III (c) II, III, I (d) III, I, II
13. Consider the following reaction. Identify the final product E:
H3 O HBr Mg / HCHO HI
CH3 MgBr + A B ether
C
H3 O
D E

(a) (b) (c) (d)

I I
I
H3C CH2I CH 2CH 3 CH 3 CH 3

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14 Consider the following reaction and identify the product:
O 
H
H2O

O O O OH O
OH
(a) OH (b) (c) (d)

OH

15. Consider the following reaction and identify the major product:
H Cl Alc.
O KOH

H
(a) O
O
H
(b) H O (c) H O (d)
O
16. Consider the following reaction. Identify the products A and B respectively:
CH 3OH CH3 OH
A CH3O – H2SO 4 B

O CH3

(a) & (b) & (c) & (d) &

H3CO OH HO CH3 H3CO HO CH3 H OH MeO CH3 H3CO H3CO OH

MnO 2
17. H2C CHCHCH 2CH 2OH A ; A is -
OH

(a) H2C CHCCH2CH 2OH (b) H2C CHCHCH 2CHO (c) H2C CHCCH2CHO (d) H2C CHCCH2COH

O OH O O O

CH3CH2 OH
18. CH CH2 H 2SO 4
find out the product :

CH2CH3 H3CH 2C
CH2CH3
(a) (b) CH2CH 3 (c) (d)
OCH2CH3
OCH2CH3 OCH2CH3 OCH2CH3
19. What will be the chief product from the following reaction sequence ?

(1) H 3PO 4, 150°C

OH (2) C6H 5CO3 H ?
O
H
(a) O (b) OH (c) (d) O
H
O
20. A chiral C7H16O2 diol is oxidized by PCC in CH2Cl2 to an achiral C7H12O2 compound. Which of the
following would satisfy these facts?

OH OH OH OH
(a) (b) (c) (d)
OH OH OH OH

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21. Which of the following is the product from ethanol addition to dihydropyran (shown below) ?

C2H5OH
H
O
OC2H5 OC2H5 OC2H 5

(a) (b) (c) (d) OC2H5

O O OC2H5 O OC2H5
22. What product(s) are expected from the following reaction ?
O
HI(excess)

O
(a) 2CH3CH2I (b) 2ICH2CH2OH (c) 2ICH2CH2 (d) CH3CH2I + CH3CH2OH
23. Which of the following reagents would be best for oxidizing a 1º-alcohol to an aldehyde ?
(a) H3PO4 (b) PCC in CH2Cl2 (c) Jonew’s reagent (H2CrO4) (d) OsO4
24. A water soluble C6H14O2 compound is oxidized by lead tetraacetate (or periodic acid) to a single C3H6O
carbonyl compound. Which of the following would satisfy this fact ?
(a) meso-2,3-dimensthoxybutane (b) 1,2-diethoxyethane
(c) meso-2,5-hexanediol (d) meso-3,4-hexanediol
25. A racemic mixture of (±) 2-phenyl propanoic acid on esterificaton with (+) 2-butanol gives two esters.
Mention the sterochemistry of two esters formed -
Me H O Et Me H O Et Me H O Me Me H O Et
(a) , (b) ,
Ph Me H Ph Me H Ph Et H Ph Me H
O O O O
       
Me H O Me Me H O Me Me H O Me Me Ph O Me
(c) , (d) ,
Ph Et H Ph Et H Ph Et H H Et H
O O O O
       
26. Compound which gives alcohol on reduction is/are (When reacts with LiAlH4)

(a) Me C Cl (b) Me C NH2 (c) Me CH CH2 (d)

O
O O
27. Which of following compound undergo acidic hydrolysis.
O O

(a) CH3 C N (b) CH3 C O Et (c) CH3 C Cl (d)

28. Which can be cleaved by HIO4 ?
O O OH O O O

(a) CH3CH2CCH2CCH 3 (b) CH3CHCCH2CH 3 (c) (d) CH3CCH2CHCH 2CCH 3

HO OH
OH

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29. Which of the following alcohol can not be oxidized by KMnO4 :
OH
OH
(a) (b) OH (c) (d)
OH

30. Which of the following reaction esterification ?


H
(a) EtOH + Acetic anhydride  (b) EtOH + CH3CO2H

O

(c) EtOH CH 3 C Cl (d) None

CH 3C C CH3I H2 / Pd / BaSO4
31. CH3 CH CH 2 X Y Z ; .Identify X, Y, Z :
O

(a) Y is CH3 CH CH 2C CCH 3 (b) Y is CH3 CH 2 CHC CCH 3

O CH 3 CCH 3

(c) Z is CH3 CH CH 2 CH CH CH5 (d) X is CH3 CHCH 2C CCH 3

O CH 3 O
32. Which is/are corect statement ?
H 3C CH3 H 3C CH3
CH 3 /OH NaOH
(a) C C H2SO4 (b) C C CH 3OH
H O CH 3 H O CH 3

nucleophile attacts here nucleophile attacts here

when epoxy linkage is cleaved when epoxy linkage is cleaved
O
O

NaBH4 H
(c) O CH3OH (d) R C OH + H O R

O
This is only afected in reduciton to 2° alcohol . These bonds undergo cleavage in the reaction
.
33. 3-methyl-3-hexanol can be prepared by -
(a) CH3MgI and 3-hexanone, followed by hydrolysis
(b) C2H5MgI and 2-Pentanone, followd by hydrolysis
(c) C3H7MgI and 2-butananone, followd by hydrolysis
(d) C4H9MgI and propanon, followed by hydrolysis
C H3

PBr3 Mg / Et 2O (1) CH 3 CH CHO

34. OH X Y (2) H2O Z .

OH CH3 H CH3

(a) X is Br (b) Y is MgBr (c) Z is C C CH3 (d) Z is C C CH3

H H H O H

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 CH CH CH CH 3
H H KMnO 4 /  SOCl2
X + Y
35. OH ; Identify the product X and Y..
D OH D O
O COCl
CH2 C Cl
(a) X is Cl C C CH 2Cl (b) X is (c) Y is (d) Y is ClCO C CH 3
D O
O D O O

36. Which one of the following alcohols can be oxidised by K2CrO4 ?

(a) Ethanol (b) Tert butyl alcohol (c) Isopropyl alcohol (d) Allyl alcohol
37. Asparmatge, an artificial sweetener is a peptide and has the following structure. Which of the following
is correct about the molecule ?
O
C6H 5
OH O

H 2N NH O
O
CH3
(a) It has four functional groups (b) It has three functional groups
(c) on hydrolysis it produces only one amino acid (d) on hydrolysis it produces a mixture of amino acids

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Comprehansion : (Q.38 to Q.40) :
Aldehydes and ketones react with oine molecule of analcohol to form compounds called hemiacetals, in
which there is one hydroyl group and one either-like group. Reaction of a hemiacetal with a second
molecule of alcohol gives an acetal and a molecule of water. We study this reaction
ROH
OH ROH
OR
O  
H H
OR OR
The carbonyl A hemiacetal An acetal (has
group of an (has an– OH and two–OR groups to
aldehyde or ketone an–OR group to the same carbon)
the same carbon)

Draw structural formulas for the hemicetal and acetal formed from these reagents. The stoichiometry of
each reaction is given in the problem.
 
H H
(a) O + 2CH 3CH2OH P (b) O + HOCH 2CH 2OH Q

Cyclohexanone Ethanol Cyclohexanone Ethylene glycol

OH
O
H
(c) + R
OH
Cyclohexanone Acetone

38. Product P is -

OEt OEt OEt OEt

(a) (b) OEt (c) OPr (d)

OEt OPr

39. Product Q is -

O
O O
(a) (b) (c) (d)
O

40. Product R is -
O O
(a) (b) O (c) O (d)

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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