ALDEHYDES AND KETONES

Section-I (Single correct)

1. O OH O O
a b
(i) (ii)

Which of the following best qualifies for a & b respectively?

(A) CH3Li ; H+ & (CH3)2CuLi ;H+ (B) (CH3)2CuLi ;H+ & CH3Li ; H+
(C) CH3ZnX ; H+ & (CH3)2CuLi ;H+ (D) CH3Br/H+ & LiAlH4

2. A mixture of 2-methylcyclohexane-1,3-dione and 3-buten-2-one is treated with

NaOH. What is the major product formed, if they undergo a sequence of reactions
which is a combination of aldol and Michael additions?
O O
(A) (B)

O O
O O
(C) (D)
O

3.
A CH 3Li D
CH 3CH 2CH 2Br B C

Select the best combination of reagents

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(A) A: ROH/KOH D: Cyclopentanone (B) A: PPh3 D: Cyclopentanone
(C) A: CuI D: Cyclopentanone (D) A: Cyclopentanone D: PPh3

1.CH3Li 2.H2O
4. Cis-crotonaldehyde ( CH3CH=CHCHO) A+B
If only 1,2-addition is considered, what is the relation between A & B ?
(A) diastereomers (B) enantiomers
(C) constitutional isomers (D) none

5. HIO4 HIO4
HOCH 2CH 2 OH A CH3CHOHCHOHCH 3 B
HIO4
Pinacol C

Correct order of equilibrium constants for cyanohydrin formation for A, B, & C is

(A) A > B > C (B) C > B > A (C) A > C > B (D) B > C > A

6. MnO2
CH 2 =CHCH 2OH A
PPh3 NaH B
CH 3CH=CHCH 2 Br
A+B
C
 C is
(A) CH 2 =CH-CH=CH-CH=CH-CH 3 (B) CH 2 =CH-CH=CH-CH=CH 2
(C) CH 2 =CH-CH 2 -CH=C=CH-CH 3 (D) None

7. Which pair of following compounds could serve as the reagents X and Y respectively
for the following conversion
PPh3 NaH
Y (CH ) CHCH=C(CH )CH CH
X 3 2 3 2 3

1.(CH3 ) 2CHCH 2 Br 2.(CH 3 ) 2 CHBr 3.CH 3CH 2CH(Br)CH 3 4.(CH3 )2 CHCHO 5.(CH 3 ) 2CO
(A) 1 & 5 (B) 3 & 4 (C) 2 & 5 (D) 2 & 4

8. Which sequence represents the best synthesis of hexanal?

(A) a) CH3CH 2 CH 2 CH 2 Br+NaC CH (B) a) CH 3CH 2CH 2CH=CH 2 +CH 3CO3 H

b) H 2 O, H 2SO 4 , HgSO 4 b) CH3 MgBr/Et 2O c) H 3O +
(C) a) CH 3CH 2 CH 2 CH 2 COCH 3/CH 3CO 3H d) PCC, CH 2Cl 2
b) LiAlH 4 ;H 2 O (D) a) CH 3CH 2 CH 2 CH 2 MgBr/ethylene oxide
c) PCC, CH 2 Cl 2 b) H 3O + c) PCC, CH 2 Cl 2

9. Select the best reagent combination for the following conversion.

O

CHEMISTRYWORLD.IN-2
(A) 1.OsO4/H2O ; NaHSO3 2. HIO4 (B)1.O3; Zn/H+ 2. OH-/
(C) RCO3H/H+ (D) O3 ; H2O2

10. When the vapour of liquid X is passed over hot Cu, a reaction occurs and the product
gives an orange color with Fehlings solution. X could be
(A) propan-1-ol (B) propan-2-ol (C) propanal (D) propanone
11. A conversion of 2,5-dimethylfuran into 2,5-dimethylpyrrole (see equation) may be
accomplished in two steps.
i) hydrolysis of the furan in aqueous acid; ii) heating the hydrolysis product with
excess ammonium carbonate
What is the intermediate hydrolysis product used in the second step?

O N
(A) 2,5-hexanedione (B) 3,4-hexanedione
(C) hexanedial (D) 2,5-dimethylcyclopentanone
12. Select the best reagent combination for the following conversion.

OHCH2C CHO OHCH2C CH3

(A) Zn-Hg; HCl (B) NH2-NH2; CH3ONa

(C) 1. Ethylene glycol; dry HCl 2. Zn-Hg; HCl 3. Dil. HCl
(D) 1. Ethylene glycol; dry HCl 2. NH2-NH2; CH3ONa 3. Dil. HCl

13. Select the correct order of equilibrium constants for the hydrate formation in the
following compounds.
O O O
CHO

O2N H2N
I II IV
NO2 III
(A) II > III > I > IV (B) III > II > I > IV (C) I > II > III > IV (D) I > II > IV > III

14. Select the best sequence of reagents for the following conversion.
OH OH
OH OH

OH O
(A) 1. HCHO/dryHCl 2. KMnO4 3. Dil.HCl

CHEMISTRYWORLD.IN-3
(B) 1. (CH3)2O/dryHCl 2. KMnO4 3. Dil.HCl
(C) 1. CH3CHO/dryHCl 2. KMnO4 3. Dil.HCl
(D) 1. PhCHO/dryHCl 2. KMnO4 3. Dil.HCl
15.
OH

OH 2 eq. PCC 1 eq.ehtylene glycol 1.CH3MgBr NaBH4

CH2Cl2 dry.HCl 2.H+
The final product of the above sequence of reactions is

(A) OH (B) OH (C) OH (D) OH

OH OH OH OH
16.
O-OH

Dil.H+

Major product of the above reaction is

(A) OH (B) O
O OH
(C) OH (D) O
O OH

17. CH3COCH3 CH2N2 A CF3COOOH B B is

(A) Ethyl acetate (B) Methyl propanoate

(C) Ethyl propanoate (D) Methyl acetate

18.
OH OH
TsOH
CH3-CH-CH2-CH-CH3 + HCHO Major product is
Meso

(A) (B)
O O O O
(C) Both A and B in equal amounts (D) None of the above
19.

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O
Dil.HCl
A + B (B gives positive Tollen's test)
O
K2Cr2O7 C is
A C

(A) COOH (B) O (C) OH (D) CHO

O

20.
O
(NH4)2CO3 Major product is

O
 (A) (B) (C) (D)
N N
N N

21.
CH2Br
1.ex PPh3 glyoxal
Major product is
2.ex. NaH
CH2Br

(A) (B) (C) (D)

22. which of the following has the maximum enol content?

(A) O (B) O (C) O (D) O

O

O
O

23. Find out the structures of B and C.

O3; Zn/H+ Dil.HCl B + C

A

CHO
(A) (B)

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CHO & CHO
&

CHO
CHO
(C) (D)
&
CHO &

CHO CHO

24. Select the correct intermediate in the following conversion.

O OH- O

(A) O O (B) O O

(C) O (D) O
H

O O
25.
CH3COCl OH- 1.CH3MgBr H+ 1.O3
A B + C D A+E+F
AlCl3 2. H 2.Zn/H+
E and F can be

(A) CHO (B) O

H
& HCHO & HCHO
O
(C) O (D) CHO
CHO CHO
&
&
CHO

26. Major product of the following reaction is

CHO
PH = 4

NH2
(A) (B) N (D) N
N (C)
N

SECTION-II Multicorrect
27. Pentaerythritol, C(CH2OH)4, used in making explosives, can be obtained by treating
(A) excess acetaldehyde with H+
(B) acetaldehyde and excess formaldehyde in basic medium
(C) treating acetaldehyde with 3 mols of formaldehyde in the presence of base and
then treating the product with LiAlH4.
D) excess formaldehyde with OH-

CHEMISTRYWORLD.IN-6
28. Vinyl alkyl ethers, RCH=CHOR1, are very rapidly hydrolysed by dilute aqueous acid to
form the alcohol R1OH and the aldehyde RCH2CHO. Hydrolysis in H2O18 gives alcohol
R1OH containing only ordinary oxygen. Select the correct statement(s).
(A) cleavage occurs through hemiacetal formation
(B) after the cleavage the aldehyde may contain O18
(C) cleavage occurs through acetal formation
(D) if the hydrolysis is carried out in D+/D2O, the resultant aldehyde may have
deuterium attached to carbon.

29. Benzaldehyde can be prepared from benzoic acid in which of the following ways.
(A) i. NaBH4 ii. H2O (B) i. LiAlH4; H+ ii. PCC
(C) i. SOCl2 ii. DIBALH/H2O (D) i. ROH/H+ ii. DIBALH/H2O

30. Select the correct statement(s).

(A) C6H5CHO > C6H5COCH3 - rate of reduction with NaBH4.
(B) Cl3CCHO > CH3CHO equilibrium constant for hydration
(C) CH2(OCH3)2 > (CH3)2C(OCH3)2 rate of acid catalysed hydrolysis
(D) Acetone > 3,3-dimethyl-2-butanone - rate of reduction with NaBH4
31.
NHN=CHCH3
NO 2
Ex.HNO3/H2SO4
HOCl/H+ A NH2 NH2 D
B C

NO2

Select correct statement(s) about D.

(A) it gives positive iodoform test. (B) it gives positive Tollens test
(C) it decolorises Br2/H2O (D) it gives bubbles with Na

32. Select the correct statement(s).

K eq PhCHO
(A) For hydrate formate formation >1
K eq acetophenone
K eq acetone
(B) For cyanohydrin formation <1
K eq CH3COC(CH3 )3
K eq cyanohydrin formation
(C) For acetaldehyde >1
K eq hydrate formation
K eq (CH3 )2C(OC2 H5 )2
(D) For hydrolysis of acetal <1
K eq CH 2 (OC2 H5 )2

33.
dil. H+
CH3-CH=CH-O-CH2-CH3 A+B
If A gives positive haloform test, select the correct statement(s) about B.
(A) It gives positive Fehlings test. (B) It reduces Ag+ to Ag.
(C) It gives off H2 with Na. (D) It decolorises Br2/H2O

CHEMISTRYWORLD.IN-7
34.
OH
O
and
O can be distinguished by
O
(A) Na (B) Lucas test (C) [Ag(NH3)2]+ (D) Fehlings solution

35. In which of the following reaction sequences, propanal is obtained as a major

product?

CH3Br 1.B2H6; THF 1.CH3MgBr PCC

(A) HC CNa (B) O
2. H202, NaOH 2.H+ CH2Cl2
dil. H+ dil. H+
(C) CH3CH2CH2-O-OH (D) CH3CH=CH-OCH3

36.
1.cold KMnO4
A 2.HIO4 B+C
 If both B and C respond positively to iodoform test, A can be

(A) Ph Ph (B) Ph H (C) Ph CH3 (D) H3C CH3

H3C CH3 H3C CH3 H CH3 H3C C2H5

37.
1.(CH3)2CuLi 1.LiAlH4
C CH3CH=CHCHO A
2.H2O (cis) 2.H2O
1.CH3Li
2.H2O
B
Select the correct statement(s).
(A) A is a mixture of diastereomers (B) B is a mixture of diastereomers
(C) A is a pure compound (D) C is a pure compound
38. Which of the following undergo(es) racemisation when dissolved in basic solution?

(A) O (B) O (C) O (D) O

Ph

(R) (R)
(R)
(R)

39. Which of the following compounds can be successfully prepared by intra-molecular

aldol condensations?

(A) O (B) O (C) O (D) O

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H H H

40

NH2OH A+ B
HCl
H+/ H+/

C D
If C is more basic than D, select the correct structural formulae for C and D.
O O
(A) (B) (C) (D)
N O O
N
N N
C C D
D
41.
1.Conc.NaOH
Ph-CH3 1.CrO2Cl2 A B+C
2.H2O 2.H+
Select the correct statement(s) about B and C.
(A) Both give off H2 with Na.
(B) Only one of them gives off CO2 with NaHCO3.
(C) Only one of them gives positive Tollens test.
(D) None of them decolorises Br2/H2O.

42.
OH
H+/ Cold HIO4 OH-/
A B C D
KMnO4
Select the correct set of products

(A) (B) (C) OH (D) O

OH

A D
A B

Q.No: 43 -45
A (CH ) CCOCH Br
(CH3 )3CCOCH 3 B (CH ) CCH(OH)CH Br
58% 3 3 2 54% 3 3 2

C (CH ) CCHCH
68% 3 3 2

CHEMISTRYWORLD.IN-9
A, B, and C are the reagents and percentage yield of each reaction is also given.
43. The best choice for A, B, & C is (A, B, & C respectively)
(A) HBr ; LiAlH4 then H2O ; RCO3H (B) Br2/H+ ; LiAlH4 then H2O ; RCO3H
(C) HBr ; LiAlH4 (D) Br2/H+ ; LiAlH4

44. If one mole of the starting compound is taken, the amount of the final product
obtained is
(A) 0.68mol (B) 0.22mol (C) 0.54mol (D) 0.58mol

45. Above conversion can be brought about in an alternate route. Select the best choice
of reagents in order of use in the alternate route.
(A) LiAlH4 then H2O ; H+/ ; RCO3H
(B) LiAlH4 then H2O ; POCl3/pyridine ; RCO3H
(C) Sn/HCl ; H+/ ; RCO3H D) None
 KEY
1.A 2.A 3.B 4.B 5.A 6.A 7.B 8.D 9.B 10.A
11.A 12.D 13.C 14.A 15.A 16.B 17.A 18.A 19.B 20.A
21.D 22.B 23.D 24.C 25.B 26.B 27.BC 28.ABD 29.BCD 30.ABD
31.AB 32.AC 33.AB 34.ACD 35.ABCD 36.BD 37.CD 38AB 39.BD 40.AB
41.AB 42.BCD 43.D 44.B 45.B

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