WORKSHEET OF CARBONYL COMPOUNDS

1. Write the structure of 3-oxopentanal. (Delhi 2009)

Answer:

2. Write the structural formula of 1-phenylpentan- 1-one.

3. What is Tollen’s reagent? Write one usefulness of this reagent.
4. Arrange the following compounds in an increasing order of their reactivity in nucleophilic
addition reactions : ethanal, propanal, propanone, butanone.
5. Give a chemical test to distinguish between Ethanal and Propanal.
6. Give a chemical test to distinguish between Propanal and Propanone.
7. Formaldehyde does not take part in Aldol condensation. Why ?
8. Aldehydes and Ketones have lower boiling points than corresponding alcohols. Why ?
9. Give the structure and IUPAC name of the product formed when propanone is reacted with
methylmagnesium bromide followed by hydrolysis. (Comptt. All India 2012)
10. Write the structure of the product formed in the following reaction : (Comptt. All India 2012)

11. Rearrange the following compounds in the increasing order of their boiling points: (All India
2013)
CH3 — CHO, CH3 — CH2 — OH, CH3 — CH2— CH3
12. Carboxylic acids do not give characteristic reactions of carbonyl group. Explain why?
13. Give a chemical test to distinguish between benzoic acid and phenol.
14. Give a test to distinguish between propan-2-one and pentan-3-one. (Comptt. All India 2014)
15. What type of aldehydes undergo Cannizaro reaction?
16. What type of aldehydes undergo Aldol condensation?
17. Arrange the following compound groups in the increasing order of their property indicated:
Propanol, Propane, Propanal
18. Name the reagents used in the following reactions : (Delhi 2015)

19. Write the reagents required in the following reactions : (All India 2015)

20. Arrange the following compounds in increasing order of their property as indicated :
(i) CH3COCH3, C6H5COCH3, CH3CHO
(reactivity towards nucleophilic addition reaction)
(ii) Cl—CH2—COOH, F—CH2—COOH, CH3—COOH (acidic character) (All India 2015)
(iii) p-nitrophenol, o- nitrophenol , m- nitrophenol, phenol( acidic character)
21. Write the equations involved in the following reactions:
(i) Wolff-Kishner reduction
(ii) Etard reaction (Delhi 2017)
22. Write the reactions involved in the following:
(i) Hell-Volhard Zelinsky reaction
(ii) Decarboxylation reaction (Delhi 2017)
23. Write the reactions involved in the following reactions: (Delhi 2017)
(i) Clemmensen reduction
(ii) Cannizzaro reaction
24. Predict the products of the following reactions : (Delhi 2015)

25. Predict the products of the following reactions : (All India 2015)
26. Write structures of compounds A, B and C in each of the following reactions: (Delhi 2017)

27. Do the following conversions in not more than two steps:

(i) Benzoic acid to benzaldehyde
(ii) Ethyl benzene to Benzoic acid
(iii) Propanone to Propene
28. (a) Illustrate the following name reactions by giving example :
(i) Cannizzaro’s reaction
(ii) Clemmensen reduction
29. (a) How are the following obtained?
(i) Benzoic acid from ethyl benzene, (ii) Benzaldehyde from toluene.
(b) Complete each synthesis by giving the missing material, reagent or products : (Delhi 2009)

30. (a) Arrange the following compounds in an increasing order of their indicated property :
(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid
strength)
(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,
(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)
(b) How would you bring about the following conversions :
(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde
(iii) Bromobenzene to 1-phenylethanol (All India 2009)

31. (a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or
a ketone.
(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute
sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic
acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the
reactions involved. (Delhi 2010)
(b) Since the organic compound (A) with molecular formula (M.F.) C 8H16O2 upon hydrolysis with
dil. H2SO4 gives carboxylic acid (B) and the alcohol (C) therefore it must be an ester. Further
since oxidation of (C) with chromic acid produces the acid (B), therefore both the carboxylic acid
(B) and the alcohol (C) must ’.contain the same number of carbon atoms.

32. (a) Give chemical tests to distinguish between the following pairs of compounds :
(i) Ethanal and Propanal (ii) Phenol and Benzoic acid
(b) How will you bring about the following conversions?
(i) Benzoic acid to benzaldehyde (ii) Ethanal to but-2-enal (iii) Propanone to propene
Give complete reaction in each case. (Delhi 2010)

33. (a) Illustrate the following name reactions giving a chemical equation in each case :
(i) Clemmensen reaction (ii) Cannizzaro’s reaction
(b) Describe how the following conversions can be brought about :
(i) Cyclohexanol to cyclohexan-1-one (ii) Ethylbenzene to benzoic acid
(iii) Bromobenzene to benzoic acid (All India 2010)

34. How are the following conversions carried out:

(i) Ethylcyanide to ethanoic acid (ii) Butan-l-ol to butanoic acid
(iii) Methylbenzene to benzoic acid
Write chemical equations for the involved reactions. (All India 2010)

35. (a) Give chemical tests to distinguish between

(i) Propanal and Propanone, (ii) Benzaldehyde and Acetophenone.
(b) How would you obtain
(i) But-2-enal from Ethanal, (ii) Butanoic acid from Butanol,
(iii) Benzoic acid from Ethylbenzene? (Delhi, All India 2011)

36. Complete the following chemical equations (Delhi 2011)

37. Complete each synthesis by giving missing reagents or products in the following : (All India
2011)

38. Illustrate the following reactions giving a suitable example for each.
(i) Cross aldol condensation (ii) Decarboxylation
(b) Give simple tests to distinguish between the following pairs of compounds :
(i) Pentan-2-one and Pentan-3-one (ii) Benzaldehyde and Acetophenone
(iii) Phenol and Benzoic acid (Delhi 2012)

39. a) Give a plausible explanation for each one of the following :

(i) There are two – NH2 groups in semicarbazide. However, only one such group is involved in
the formation of semicarbazones.
(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.
(b) An organic compound with molecular formula C9H10O forms 2, 4, – DNP derivative, reduces
Tollens’ reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-
benzene-di- carboxylic acid. Identify the compound. (Delhi 2012)

40. (a) Give chemical tests to distinguish between

(i) Phenol and Benzoic acid (ii) Benzophenone and Acetophenone
(b) Write the structures of the main products of following reactions : (Delhi 2012)

41. (a) An organic compound ‘A’ with molecular formula C 8H8O forms an orange red precipitate
with 2,4-DNP reagent and gives yellow precipitate on heating with I2 and NaOH. It neither
reduces Tollen’s reagent nor Fehling’s reagent nor does it decolourize bromine water or
Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a carboxylic acid ‘W having
molecular formula C7H6O2. Identify the compounds ‘A’ and ‘B’ and explain the reactions
involved.
(b) Write the mechanism of esterification of carboxylic acids. (Comptt. Delhi 2012)

42. (a) An organic compound ‘A’ which has characteristic odour, on treatment with NaOH forms
two compounds ‘B’ and ‘C’. Compound ‘B’ has the molecular formula C 7H8O which on oxidation
with CrO3 gives back compound ‘A’. Compound ‘C’ is the sodium salt of the acid. ‘C’ when
heated with soda lime yields an aromatic hydrocarbon ‘D’. Deduce the structures of ‘A’, ‘B’, ‘C’
and ‘D’.
(b) Give reasons :
(i) Electrophilic substitution in Benzoic acid takes place at meta position.
(ii) Carboxylic acids do not give characteristic reactions of carbonyl group. (Comptt. Delhi 2012)

43. (a) Give chemical tests to distinguish between the following pairs of compounds :
(i) Benzene amide and 4-aminobenzoic acid (ii) Methyl acetate and Ethyl acetate
(b) An organic compound with molecular formula C9H10O forms 2, 4-DNP derivative and reduces
Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation, it gives 1,2-
benzenedicarboxylic acid. Identify the compound and write chemical equations for the reactions.
(Comptt. All India 2012)

44. (a) Although phenoxide ion has more number of resonating structures than carboxylate ion,
carboxylic acid is a stronger acid than phenol. Give two reasons.
(b) How will you bring about the following converstions?
(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde
(iii) Ethanal to but-2-enal (Delhi 2013)

45. a) How will you convert the following :

(i) Propanone to Propan-2-ol (ii) Ethanal to 2-hydroxy propanoic acid
(iii) Toluene to benzoic acid
(b) Give simple chemical test to distinguish between :
(i) Pentan-2-one and Pentan-3-one (ii) Ethanal and Propanal (All India 2013)
46. a) Write the products of the following reactions :

b) Which acid of each pair shown here would you expect to be stronger? (All India 2013)

47. Two moles of organic compound ‘A’ on treatment with a strong base gives two compounds
‘B’ and ‘C’. Compound ‘B’ on dehydrogenation with Cu gives ‘A’ while acidification of ‘C’ yields
carboxylic acid ‘D’ with molecular formula of CH 2O2. Identify the compounds A, B, C and D and
write all chemical reactions involved. (Comptt. Delhi 2013)

48. a) How will you carry out the following conversions?

(i) Acetylene to Acetic acid (ii) Toluene to m-nitrobenzoic acid
(iii) Ethanol to Acetone
(b) Give reasons :
(i) Chloroacetic acid is stronger than acetic acid.
(ii) pH of reaction should be carefully controlled while preparing ammonia derivatives of carbonyl
compounds. (Comptt. Delhi 2013)

49. (a) How will you obtain the following :

(i) Benzaldehyde from Phenol (ii) Benzoic acid from Aniline
(b) Give reasons :
(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.
(ii) Electrophilic substitution in benzoic acid takes place at meta position.
(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.

50. (a) Write the products of the following reactions :

51. (a) Account for the following :
(i) CH3CHO is more reactive than CH3COCH3 towards reaction with HCN.
(ii) Carboxylic acid is a stronger acid than phenol.
(b) Write the chemical equations to illustrate the following name reactions :
(i) Wolff-Kishner reduction (ii) Aldol condensation (iii) Cannizzaro reaction (Delhi 2014)

52. (a) Write the products formed when CH3CHO reacts with the following reagents :
(i) HCN (ii) H2N – OH (iii) CH3CHO in the presence of dilute NaOH
(b) Give simple chemical tests to distinguish between the following pairs of compounds :
(i) Benzoic acid and Phenol (ii) Propanal and Propanone. (All India 2014)

53. a) Account for the following :

(i) Cl – CH2COOH is a stronger acid than CH3COOH.
(ii) Carboxylic acids do not give reactions of carbonyl group.
(b) Write the chemical equations to illustrate the following name reactions :
(i) Rosenmund reduction (ii) Cannizzaro’s reaction
(c) Out of CH3CH2 – CO – CH2 – CH3 and CH3CH2 – CH2 – CO – CH3, which gives iodoform
test? (All India 2014)

54. (a) Draw the structures of the following compounds:

(i) 4-chloropentan-2-one (it) But-2-en-l-al
(b) Write the product(s) in the following: (Comptt. Delhi 2014)

55. (a) Describe the following actions

(i) Acetylation (ii) Aldol condensation
(b) Write the main product in the following equations : (Comptt. Delhi 2015)
56. (a) Draw the structures of the following derivatives :
(i) Propanone oxime (ii) Semicarbazone of CH3CHO
(b) How will you convert ethanal into the following compounds? Give the chemical equations
involved. (Comptt. All India 2015)

57. Write the structures of A, B, C, D and E in the following reactions : (Delhi 2016)

58. (a) Write the chemical equation for the reaction involved in Cannizzaro reaction.
(b) Draw the structure of the semicarbazone of ethanal.
(c) Why pKa of F—CH2—COOH is lower than that of Cl—CH2—COOH?
(d) Write the product in the following reaction:

59. A and B are two functional isomers of compound C 3H6O. On heating with NaOH and I2,
isomer B forms yellow precipitate of iodoform whereas isomer A does not form any precipitate.
Write the formulae of A and B. (All India 2016)

60. a) Write the product(s) in the following :

61. (a) Give reasons :

(i) CH3—CHO is more reactive than CH3COCH3 towards HCN.
(ii) 4-nitrobenzoic acid is more acidic than benzoic acid.
(b) Describe the following :
(i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation (Comptt. Delhi 2016)

62. (b) Complete the following : (Comptt. All India)

63. Write the product(s) in the following reactions. (Delhi 2017)

64. (a) Write the product(s) in the following reactions:

65. a) Write the reactions involved in the following:

(i) Etard reaction (ii) Stephen reduction
(b) How will you convert the following in not more than two steps:
(i) Benzoic acid to Benzaldehyde (ii) Acetophenone to Benzoic acid
(iii) Ethanoic acid to 2-Hydroxyethanoic acid
66. a) How will you convert:
(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol
(b) Give reasons :
(i) Electrophilic substitution in benzoic acid takes place at meta position.
(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of
comparable molecular masses.
(iii) Propanal is more reactive than propanone in nucleophilic addition reactions. (Comptt. Delhi
2017)

67. a) Write the products of the following reactions :

68. a) Write structures of A, B, C and D in the following reaction sequence :

(b) Arrange the following compounds in the increasing order of their boiling points :
CH3CHO, CH3CH2OH, CH3OCH3, CH3COOH. (Comptt. All India 2017)