Sure Shot Questions

Chapter – 08
Aldehydes, Ketones and Carboxylic Acids
MCQ 4. The reagent which does not react with both,
acetone and benzaldehyde is ________.
1. Addition of water to alkynes occurs in acidic
(a) Sodium hydrogensulphite
medium and in the presence of Hg2+ ions as a
(b) Phenyl hydrazine
catalyst. Which of the following products will be
(c) Fehling’s solution
formed on addition of water to but-1-yne under
(d) Grignard reagent
these conditions?
5. Cannizzaro’s reaction is not given by ______.

6.

Structure of ‘A’ and type of isomerism in the above

reaction are respectively
(a) Prop-1-en-2-ol, metamerism
2. The correct order of increasing acidic strength is
(b) Prop-1-en-1-ol, tautomerism
_______.
(c) Prop-2-en-2-ol, geometrical isomerism
(a) Phenol < ethanol < chloroacetic acid < acetic
(d) Prop-1-en-2-ol, tautomerism.
acid
7. Compounds (A) and (C) in the following reactions
(b) Ethanol < phenol < chloroacetic acid < acetic
are
acid
(c) Ethanol < phenol < acetic acid < chloroacetic
acid
(d) Chloroacetic acid < acetic acid < phenol <
(a) Identical
ethanol
(b) Positional isomers
(c) Functional isomers
3. Compound can be prepared by (d) Optical isomers.
reaction of _____. 8. Which is the most suitable reagent for the
(a) Phenol and benzoic acid in the presence of following conversion?
NaOH
(b) Phenol and benzoyl chloride in the presence of
pyridine
(c) Phenol and benzoyl chloride in the presence of
(a) Tollens’ reagent
ZnCl2
(b) Benzoyl peroxide
(d) Phenol and benzaldehyde in the presence of
(c) I2 and NaOH solution
palladium
(d) Sn and NaOH solution

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9. Which of the following compounds will give 16. Assertion: The final product in Aldol condensation
butanone on oxidation with alkaline KMnO4 is always  ,  -unsaturated carbonyl compound.
solution? Reason:  ,  -unsaturated carbonyl compounds
(a) Butan-1-ol (b) Butan-2-ol
are stabilized due to conjugation.
(c) Both of these (d) None of these
(a) Both Assertion (A) and Reason (R) are true
10. In Clemmensen reduction, carbonyl compound is
and Reason (R) is the correct explanation of
treated with ________.
the Assertion (A)
(a) Zinc amalgam + HCl
(b) Both Assertion (A) and Reason (R) are true,
(b) Sodium amalgam + HCl
but Reason (R) is not the correct explanation
(c) Zinc amalgam + nitric acid
of the Assertion (A)
(d) Sodium amalgam + HNO3
(c) Assertion (A) is true, but Reason (R) is False.
11. Iodoform test is not given by [2020]
(d) Assertion (A) is false, but Reason (R) is true.
(a) ethanol (b) ethanal
17. Assertion (A): Reactivity of ketones is more than
(c) pentan-2-one (d) pentan-3-one
aldehydes.
Reason (R): The carbonyl carbon of ketones is less
12. What is the correct IUPAC name of the given
electrophilic as compared to aldehydes.
compound? [2020]
(a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) is the correct
explanation of the Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct
(a) 2, 2-Dimethylbutanoic acid statements, but Reason (R) is not the correct
(b) 2-Carboxyl – 2 – methylbutane explanation of the Assertion (A).
(c) 2-Ethyl-2-methylpropanoic acid (c) Assertion (A) is correct, but Reason (R) is
(d) 3-Methylbutanecarboxylic acid incorrect statement.
13. Which one of the following has lowest pKa value? (d) Assertion (A) is incorrect, but Reason (R) is
[2023] correct statement. [2020]
(a) CH3  COOH 18. Assertion (A) : Oxidation of ketones is easier than
(b) O2 N  CH 2  COOH aldehydes.
Reason (R): C-C bond of ketones is stronger than
(c) Cl  CH 2  COOH
C-H bond of aldehydes.
(d) HCOOH (a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) is the correct
explanation of the Assertion (A).
14. The oxidation of toluene to benzaldehyde by (b) Both Assertion (A) and Reason (R) are correct
chromyl chloride is called statements, but Reason (R) is not the correct
(a) Etard reaction explanation of the Assertion (A).
(b) Riemer-Tiemann reaction (c) Assertion (A) is correct, but Reason (R) is
(c) Stephen's reaction wrong statement.
(d) Cannizzaro's reaction. (d) Assertion (A) is wrong, but Reason (R) is
15. Which of the following tests/ reactions is given by correct statement. [2020]
aldehydes as well as ketones? [2022 – 23] 19. Assertion: Benzoic acid does not give Friedel-Crafts
(a) Fehling's test (b) Tollens' test reaction.
(c) 2,4-DNPtest (d) Cannizzaro reaction Reason: The carboxyl group is deactivating and
gets bonded to Lewis acid AICI3.
 Assertion-Reasoning (a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) is the correct
explanation of the Assertion (A).

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 (b) Both Assertion (A) and Reason (R) are correct
statements, but Reason (R) is not the correct
explanation of the Assertion (A).
(c) Assertion (A) is correct, but Reason (R) is
incorrect statement.
(d) Assertion (A) is incorrect, but Reason (R) is
correct statement. [2021 C]
20. Assertion (A) ; Benzoic acid does not undergo
Friedal-Crafts reaction.
Reason (R) : The carboxyl group is activating and
undergoes electrophilic substitution reaction.
(a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) is the correct
explanation of the Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct
statements, but Reason (R) is not the correct
explanation of the Assertion (A).
(c) Assertion (A) is correct, but Reason (R) is
incorrect statement.
(d) Assertion (A) is incorrect, but Reason (R) is
correct statement. [2020]
21. Assertion : Carboxylic acids are more acidic than
phenols.
Reason: Phenols are ortho and pora-directing.
(a) Assertion and reason both are correct
statements and reason is correct explanation for
assertion.
(b) Assertion and reason both are correct
statements but reason is not correct explanation
for assertion.
(c) Assertion is correct statement but reason is
wrong statement.
(d) Assertion is wrong statement but reason is
correct statement. [2020 – 21]

Case study Questions

22. Read the text carefully and answer the questions:
(A), (B) and (C) are three non - cyclic functional
isomers of a carbonyl compound with molecular
formula C4H8O. Isomers (A) and (C) give positive
Tollens test whereas isomer (B) does not give
Tollen’s test but gives positive iodoform test.
Isomers (A) and (B) on reduction with Zn(Hg)/conc.
HCl give the same product (D).
23. Read the text carefully and answer the
questions: When an aldehyde with noα - hydrogen
reacts with concentrated aqueous NaOH, half the
aldehyde is converted to carboxylic acid salt and other
half is converted to an alcohol. In other words, half of
the reactant is oxidized and other half is reduced. This
reaction is known as Cannizzaro reaction.

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Questions
24. Write the reaction involved in the following: Stephen reduction.
25. How do you convert the following:
Toluene to benzoic acid?
26. Do the following conversion in not more than two steps:
Ethyl benzene to benzoic acid
27. Write the equations involved in the following reactions: [Delhi 2017]
(i) Clemmensen reduction
(ii) Cannizzaro reaction
28. (a) Write the product in the following reaction:

(b) Give simple chemical test to distinguish between the following pair of compounds:
Butanal and Butan – 2 – one. [2/5, Al 2017]
29. An organic compound ‘A’ having the molecular formula C3H8O on treatment with Cu at 573K, gives ‘B’. ‘B’ does
not reduce Fehling’s solution but gives a yellow precipitate of the compound ‘C’ with l2/NaOH. Deduce the
structures of A, B and C.

30. (i) Distinguish with a suitable chemical test:

(1) CH3COCH2CH3 and CH3CH2CH2CHO
(2) Ethanal and Ethanoic acid

(ii) Write the structure of oxime of acetone.

(iii) Identify A to D.

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31. Draw the structures of the following:
(i) 𝑝 − 𝑀𝑒𝑡ℎ𝑦𝑙𝑏𝑒𝑛𝑧𝑎𝑙𝑑𝑒ℎ𝑦𝑑𝑒
(ii) 4 − 𝑀𝑒𝑡ℎ𝑦𝑙𝑝𝑒𝑛𝑡 − 3 − 𝑒𝑛 − 2 − 𝑜𝑛𝑒

32. Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction:
𝐶𝐻3 𝐶𝐻𝑂, 𝐶6 𝐻5 𝐶𝑂𝐶𝐻3 , 𝐻𝐶𝐻𝑂

33. Complete each synthesis by giving missing starting material, reagent or products.

34. Give chemical tests to distinguish between the following pairs of compound :
(i) Propanal and Propanone
(ii) Acetophenone and Benzophenone
(iii) Phenol and Benzonic acid

35. How would you bring about the following conversions? Write the complete equation in each case.
(i) Ethanal to 3-hydroxybutanal
(ii) Benzoic acid to m – nitrobenzyl alcohol
(iii) Benzaldehyde to benzophenone

36. Arrange the following in order of property indicated for each set.
(i) 𝐶𝐻3 𝐶𝐻𝑂, 𝐶𝐻3 𝐶𝐻2 𝑂𝐻, 𝐶𝐻3 𝑂𝐶𝐻3 , 𝐶𝐻3 𝐶𝐻2 𝐶𝐻3(increasing order of boiling points)
(ii) (𝐶𝐻3 )2 𝐶𝐻𝐶𝑂𝑂𝐻, 𝐶𝐻3 𝐶𝐻2 𝐶𝐻(𝐵𝑟)𝐶𝑂𝑂𝐻, 𝐶𝐻3 𝐶𝐻(𝐵𝑟)𝐶𝐻2 𝐶𝑂𝑂𝐻(increasing order of their acid strengths )
(iii) ethanol, propanal, propanone, butanone (increasing order of reactivity in nucleophilic addition reactions)

37. A and B are two functional isomers of compound 𝐶3 𝐻6 𝑂. On heating with Na OH and 𝐼2 , isomer A forms yellow
precipitate of iodoform whwereas isomer B does not form any precipitate. Write the formulae of A and B.

38. An alkene ‘A’ molecular formula (𝐶5 𝐻10 ) on ozonolysis give a mixture of two compounds ‘B’ and ‘C’. Compound
‘B’ gives positive Fehling’s test and also reacts with iodine and 𝑁𝑎𝑂𝐻 solution. Compound ‘C’ does not give
Fehling’s test but forms iodoforms. Identify the compounds ‘A’, ‘B’ and ‘C’ giving suitable explanation and write
the reactions of ozonolysis and iodoform formation from either ‘B’ or ‘C’.

39. Write down functional isomers of a carbonyl compound with molecular formula 𝐶3 𝐻6 𝑂. Which isomer will react
faster with HCN and why? Explain the mechanism of the reaction also. Will the reaction lead to the completion

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 with the conversion of whole reactant into product at reaction conditions? If a strong acid is added to the
reaction mixture what will be the effect on concentration of the product and why?

40. An organic compound with the molecular formula 𝐶9 𝐻10 𝑂 forms 2, 4-DNP derivative, reduces Tollens’ reagent
and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2- benzenedicarboxylic acid , Identify the
compound.

41. Arrange the following in the decreasing order of their acidic character.
(i) HCOOH, 𝐶𝐻3 𝐶𝐼𝐶𝑂𝑂𝐻, 𝐶𝐹3 𝐶𝑂𝑂𝐻, 𝐶𝐶𝐼3 𝐶𝑂𝑂𝐻
(ii) 𝐶6 𝐻5 𝐶𝑂𝑂𝐻, 𝐹𝐶𝐻2 𝐶𝑂𝑂𝐻, 𝑁𝑂2 𝐶𝐻2 𝐶𝑂𝑂𝐻
(iii) 𝐶𝐻3 𝐶𝐻2 𝑂𝐻, 𝐶𝐻3 𝐶𝑂𝑂𝐻, 𝐶𝐼𝐶𝐻2 𝐶𝑂𝑂𝐻, 𝐹𝐶𝐻2 𝐶𝑂𝑂𝐻, 𝐶6 𝐻5 𝐶𝐻2 𝐶𝑂𝑂𝐻

42. How would you account for the following:

(i) Aldehydes are more reactive than ketones towards nucleophiles.
(ii) The boiling points of aldehydes and ketones are lower than of the correspoinding acids.
(iii) The aldehydes and ketones undergo a number of addition reactions.

43. An organic compound ‘X’ having molecular formula 𝐶4 𝐻8 𝑂 gives orange-red ppt. with 2, 4-DNP reagent. It does
not reduce Tollens’ reagent but gives yellow ppt. of iodoform on heating with 𝑁𝑎𝑂𝐼. Compound X on reduction
with 𝐿𝑖𝐴𝐼𝐻4 gives compound ‘Y’ which undergoes dehydration reaction on heating with conc. 𝐻2 𝑆𝑂4 to form but
-2-ene. Identfy the compounds X and Y.

44. Illustrate the following reactions giving a suitable example for each:
(i) Cross aldol condensation (ii)Decarboxylation

45. What is meant by the following terms? Give an example in each case.
(i) Cyanohydrin (ii) Semicarbazone (iii)Hemiacetal
(iv)Ketal (v) 2, 4-DNP derivative.

46. An organic compound ‘A’ with molecular formula 𝐶8 𝐻8 𝑂 gives positive DNP and iodoform test. It does not
reduce Tollens’ or Fehling’s reagent and does not decolourise bromine water also. On oxidation with chromic
acid (𝐻2 𝐶𝑟𝑂4 ), it gives a carboxylic acid (B) with molecular formula 𝐶7 𝐻6 𝑂2 . Deduce the structures of A and B.
47. Predict the products of the following reactions:

48. Complete each synthesis by giving missing starting material, reagent or products.

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49. (a) Account for the following:
(i) 𝐶𝐼 − 𝐶𝐻2 𝐶𝑂𝑂𝐻 is a stronger acid than 𝐶𝐻3 𝐶𝑂𝑂𝐻.
(ii) Carboxylic acids do not give reactions of carbonyl group.
(b) Out of 𝐶𝐻3 𝐶𝐻2 − 𝐶𝑂 − 𝐶𝐻2 − 𝐶𝐻3 𝑎𝑛𝑑 𝐶𝐻3 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝑂 − 𝐶𝐻3 , which gives iodoform test?

50. How will you bring about the following conversions in not more than two steps?
(i) Propanone to Propene
(ii) Benzoic acid to Benzaldehyde
(iii) Ethanol to 3-Hydrozybutanal
(iv) Benzene to m-Nitracetophenone
(v) Benzaldehyde to Benzophenone

51. Arrange the following compounds in increasing order of their property as indicated:
(i) 𝐶𝐻3 𝐶𝐻2 𝐶𝐻(𝐵𝑟)𝐶𝑂𝑂𝐻, 𝐶𝐻3 𝐶𝐻 (𝐵𝑟)𝐶𝐻2 𝐶𝑂𝑂𝐻, (𝐶𝐻3 )2 𝐶𝐻𝐶𝑂𝑂𝐻, 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝑂𝑂𝐻 (acid strength)
(ii) Benzoic acid, 4-Nitrobenzonic acid, 3, 4 – Dinitrobenzoic acid, 4- Methoxybenzoic and (acid strength)

52. Account for the following :

(a) Aromatic carboxylic acids do not undergo Friedel- Crafts reaction.
(b) 𝑝𝐾𝑎 value of 4-nitrobenzoic acid is lower than that of benzoic acid.

53. Give chemical tests to distinguish between:

(i) Acetaldehyde and benzaldehyde (ii) Propanone and propanol.

54. (a) Give reasons for the following:

(i) Ethanal is more reactive than acetone towards nucleophilic addition reaction.
(ii) (𝐶𝐻3 )3 𝐶 − 𝐶𝐻𝑂 does not undergo aldol condensation.
(iii) Carboxylic acids are higher boiling liquids than alcohols.
b) Give a simple chemical test to distinguish between:
(i) Acetophenone and Benzophenone
(ii) Benzaldehyde and Ethanal

55. Predict the products of following reactions

(𝑖)𝐾𝑀𝑛𝑂4 /𝐾𝑂𝐻
(i) 𝐶6 𝐻5 − 𝐶𝐻2 − 𝐶𝐻3 →
(𝑖)𝑁𝐻3 /∆
(ii) 𝐶𝐻3 𝐶𝑂𝑂𝐻 → ?

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