EXCEL 2022

ALDEHYDE & KETONE

ALDOL AND CANNIZARO 07 I

Marking Scheme : Single Correct (+3,-1) M M: 177 Time : 2 hr

1. Mixed aldol reactions require
(a) Only one of the reactants to be able to form an enolate
(b) One of the reactants to be more reactive towards the nucleophile
(c) Much stronger bases (d) B and C
2. Benzyl alcohol is obtained from benzaldehyde by-
(a) Fittig's reaction (b) Cannizaro's reaction (c) Kolbe's reaction (d) Wurtz's reaction
CHO

10% NaOH (1) NaOCl

3. + Acetone 30°C
A (2) H
 B(major product) . ‘B’ is

COO Na COONa Ph COOH

(a) Ph
(b) Ph (c) COOH
(d) Ph
O
OH
4. Predict the product of the following aldol condensation. 2 H –H 2O

O H H O O H O H

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

5. Predict the major product of the following reaction.

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

6. Choose the major product of the following reaction.

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

7. Predict the product of the following reaction:

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

8. What starting material is required for the following reaction?

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

9. If formaldehyde and potassium hydroxide are heated, then we get-

(a) Acetylene (b) Methane (c) Methyl alcohol (d) Ethyl formate

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 O
H NaOH
10. Predict the product of the following reaction.
O O O
O

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

11. Identify compound (A)

(a) CH3CHO (b) CH3CH2CHO (c) CHO (d) CHO

12. Choose the major product of the following aldol reaction.

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

13. Predict the major product of the following reaction.

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

14. Predict the product of the following reaction sequence.

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

15. Choose the product of the following reaction sequence.

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

16. What compound results from the aldol cyclization of

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

17. The aldol cyclization of produces which of these ?

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

18. What would be the product, C, of the following reaction sequence ?

(C)

(a) (CH3)3CCH2CH2CH2OH (b) (c)

(d) (e)

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19. Which reagents would you use to synthesize this compound by an aldol condensation ?

(a) and (b) and

(c) and (d) and (e) and

20. Which of these is not among the reaction products when a crossed aldol addition occurs between ethanal
and butanal ?

(a) (b) (c)

(d) (e)

21. What would be the major product of the following reaction ?

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

22. Which is the only one of these compounds which cannot self-condense in the presence of dilute aqueous
alkali ?
(a) Phenylethanal (b) Propanal (c) 2-Methylpropanal (d) 3-Methylpentanal (e) 2,2-Dimethylpropanal
23. Aldehyde V was treated with base to give the product shown. Which of the following aldehydes is
compound V ?

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

24.

(a) Final product B is (b) Final product B is

(c) Final product B is (d) A B is intermolecular aldol.

25. Which of the following is the product of aldol condensation?

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

26. Number of -bond present in compound B.

(a) 6 (b) 7 (c) 8 (d) 9

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27. The product of the following reaction are:

(a) and (b) and

(c) and (d) and

28.

Number of possible intramolecular aldol products.(Excluding 100ereo)

(a) 1 (b) 2 (c) 3 (d) 4

conc. KOH H
29. M N 
O

O
Compound M is obtained by which of the following reaction
O
CH2–OH C–O–Et
2 moles of PCC 2 moles of
(a) in CH 2Cl 2
(b) DIBAL-H
CH2–OH C–CH3
O

O O
C–O–Et
2 moles of CH3MgBr
(c) DIBAL-H (d)
C–CH3
O

OH

CHCl 3 + KOH 50% KOH

30. The end product(s) of the reaction X 
Y .is/are:

OH OH OH OH

(a) (b) OH and COOH

OH OH O
OH
C COOK
(c) OH and COOK (d)

31. ; (X) is:

(a) (b)

(c) (d)

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  
32. In Cannizzaro reaction given below, 2PhCHO  ÖH PhCH2OH + PhCÖ 2
The slowest step is:
(a) the abstraction of proton from the carboxylic group (b) the deprotonation of PhCH2OH

(c) the attack of ÖH at the carboxyl group (d) the transfer of hydride to the carbonyl group

33. (x) and (y) are:

(a) (b) (c) (d) None

34. (A) major. Product (A) is:

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

35. The Cannizzaro reaction is not given by

(a) trimethyl acetaldehyde (b) acetaldehyde (c) benzaldehyde (d) formaldehyde
36. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives:
(a) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(b) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(c) m-chlorobenzyi and m-hydroxybenzyl alcohol
(d) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
37. Total number of different cross aldol condensation product (only structural) obtained when a mixture of
(S) 2-methyl cyclohexanone and 2-butanone is treated with aqueous sodium hydroxide:

(a) 2 (b) 3 (c) 4 (d) 5

38. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
(a) benzyl alcohol and sodium formate (b) sodium benzoate and methyl alcohol
(c) sodium benzoate and sodium formate (d) benzyl alcohol and methyl alcohol
39. The number of aldol reaction (s) that occurs in the given transformation is:

(a) 1 (b) 2 (c) 3 (d) 4

CHO OHC

(1) NaOH (excess) 100°C

40. (2) H / H 2O
any one of the products formed is:

CHO OHC O
COOH HOOC CH 2OH HOH2C CH 2OH HOOC O

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

O
COOH HOOC CH 2OH HOH2C COOH HOH2C
O

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41. Find out the product of the following reaction:
conc. KOH


H O

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

OCOO K
COO K OH COO K COO K COO K CH 2OH
OH

42. Predict the major product of the following reaction sequence.

O O
OLi

CH3 H3 C –H2O 1.
+ NaOH  2. H 2O

CH3 CH3

O O O O O O O O

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

CH 3 CH 3
O3 KOH
43. Zn A 
B Major product B is:
O O O O

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

44. Products (P) and (Q) respectively are:

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

45. (x) can't be:

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

46. Which of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding
alcohol and acid ?
(a) Phenol (b) Benzoic acid (c) Butanai (d) Benzaldehyde
47. Total number of intramolecular aldol condensation products possible from given compound is (excluding
stereoisomer).

(a) 1 (b) 2 (c) 3 (d) 4

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 (1) O 3, Zn
(2) conc KOH
OH + HCO 2K
48. A Major product B is:
HBr
CCl 4 B (major)

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

Br
Br
OH

PCC dil. KOH

49. A + HCHO B Major product B is:
O O O O
OH

OH
(a) (b) CH 3 (c) (d)

50. If ; Possible structure of X is:

CH 3

(a) (b) (c) H 3C (d)

H 3C CH3 CH3 CH 3
51. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the

following lactone as the only product?

COOCH 3 COOH CHO COOH

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

COOH CHO CHO COOH
52. In a Cannizzaro reaction the intermediate which is the best hydride doner is:
H H H H
O O
(a) C6H5 C O (b) C6H5 C O (c) (d)
O2N O CH3O O
OH O
53. Tischenko reaction is a modification of:
(a) Aldol condensation (b) Claisen condensation (c) Cannizzaro reaction (d) Pinacol-pinacolon rxn.
54. Which is the major product (B) of the following reaction?
O O
(1) EtONa, EtOH (2) NaOH / I 2
 A B
H 3C CH3
O O O O

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

O3 conc. KOH H
55. Identify Z from the following reaction? Zn X Y  Z
(Phenanthrene)

O O
O
C OK
(a) CH2 OH (b) O (c) O (d) C O
CH2 CH2

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56. Find the compound B In the given reaction sequence.

(1) OH NH2NH 2 / OH
(2) C6H 5CHO /  A B

(a) CH C6H5 (b) (c) CH 2 C6H5 (d)

CH C 6H5 CH2 C6H5

57. What would be the major product of the following reaction at 100°C?
O O

H3CCCH 3
H 3C CH + OH
100°C

(a) (b) (c)

(d) (e)

58. The aldol reaction of cyclohexanone produces which of these self-condensation products?
O O O O O O

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

OH H
59. Choose the reactant that would give the product shown. ?
O O O

CH 3 O COOCH 3
(a) (b) (c) (d)
O O O O

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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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