PATI SIR CHEMISTRY

IMPORTANT QUESTIONS
Class- XII || ALDEHYDES, KETONES & CARBOXYLIC ACIDS || CHEMISTRY

1. Name the reagent to bring about the following transformations:

(a) Pent-3-en-2-ol to pent-3-en-2-one, (b) But-1-yne to butan-2-one, (c) p-
nitrotoluene to p-nitrobenzaldehyde.
2. Name the product obtained when calcium acetate is heated strongly and distilled.
3. What happens when the vapours of acetic acid are passed over manganous oxide at 575 K?
4. Name the compound from which pinacol is obtained.
5. Name the reaction and the reagent used for the conversion of acid chlorides to the
corresponding aldehydes.
6. Name one reagent used to convert phenol into salicylaldehyde.
7. Name the reagent used to convert benzene into benzaldehyde in Gatterman-Koch aldehyde
synthesis.
8. What happens when benzyl chloride is boiled with copper nitrate solution in a current of CO2?
9. What type of reactions are given by the carbonyl group in aldehydes and ketones?
10. What happens when hydrogen peroxide reacts with formaldehyde in pyrogallol?
11. Name two methods which are commonly used to convert C = O group into a CH2 group.
12. What are the products obtained by the reductive ozonolysis of penta-1,3-diene?
13. Give the structure and IUPAC name of an aliphatic aldehyde having five carbon atoms
which undergoes Cannizzaro reaction.
14. Arrange the following in order of their increasing reactivity towards HCN:
CH3CHO, CH3COCH3, HCHO, C2H5COCH3.
15. Name the product obtained when acetaldehyde reacts with excess of ethyl alcohol in
presence in dry HCl gas.
16. How will you convert acetone into 2-methyl propane-2-ol?
17. How will you convert acetaldehyde into propan-2-ol?
18. How will you convert benzaldehyde into 1-phenyl-1-ethanol?
19. Name the reaction when ketones are reduced to secondary alcohols with aluminum
isopropoxide in 2-propanol solution.
20. Write one chemical reaction to illustrate Wacker’s process for converting ethylene into
ethanal.
21. Write chemical reaction of formic acid and Fehling’s solution.
22. How does formic acid react with Tollens’ reagent?
23. What makes acetic acid stronger acid than phenol?
24. Write the structure of active valeric acid.
25. Give a suitable example of HVZ reaction.
26. How is acetic acid obtained from methanol in one step?
27. Suggest a suitable oxidizing agent for the conversion of
(CH3)2 C = CHCOCH3 → (CH3)2C = CHCOOH

O
28. Why carboxylic acid (⎯ C ⎯ OH) do not form oximes?
29. Why does benzoic acid not undergo Friedel-Craft reaction?
30. What happens when benzoic acid is heated with hydrazoic acid in presence of conc. H2SO4?

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31. Write the structures of the following compounds.
(i) a-Methoxypropionaldehyde (ii) 3-Hydroxybutanal
(iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal
(v) Di-sec. butyl ketone (vi) 4-Fluoroacetophenone
32. Give names of the reagents to bring about the following transformations:
(i) Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone
(iii) p-Fluorotoluene to p-fluorobenzaldehyde (iv) Ethanenitrile to ethanal
(v) Allyl alcohol to propenal (vi) But-2-ene to ethanal
33. Write the structures of products of the following reactions:

34. Arrange the following compounds in the increasing order of their boiling points:
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2-O-C2H5, CH3CH2CH2CH3
35. Arrange the following compounds in increasing order of their boiling points.
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
36. Would you expect benzaldehyde to be more reactive or less reactive in nucleophilic
addition reactions than propanal? Explain your answer.
37. An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate
with 2,4-DNP reagent and gives yellow precipitate on heating with iodine in the presence
of sodium hydroxide. It neither reduces Tollens’ or Fehlings’ reagent, nor does it
decolourise bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it
gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A)
and (B) and explain the reactions involved.
38. Arrange the following compounds in increasing order of their reactivity in nucleophilic
addition reactions.
(i) Ethanal, Propanal, Propanone, Butanone.
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
Hint: Consider steric effect and electronic effect.
39. Predict the products of the
following reactions:

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40. Give the IUPAC names of the following compounds:
(i) Ph CH2CH2COOH (ii) (CH3)2C=CHCOOH

41. Write chemical reactions to affect the following transformations:

(i) Butan-1-ol to butanoic acid
(ii) Benzyl alcohol to phenylethanoic acid
(iii) 3-Nitrobromobenzene to 3-nitrobenzoic acid
(iv) 4-Methylacetophenone to benzene-1,4-dicarboxylic acid
(v) Cyclohexene to hexane-1,6-dioic acid
(vi) Butanal to butanoic acid.
42. Show how each of the following compounds can be converted to benzoic acid.
(i) Ethylbenzene (ii) Acetophenone
(iii) Bromobenzene (iv) Phenylethene (Styrene)
43. Which acid of each pair shown here would you expect to be stronger?
(i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H
(iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H

44. What is meant by the following terms ? Give an example of the reaction in each case.
(i) Cyanohydrin (ii) Acetal
(iii) Semicarbazone (iv) Aldol
(v) Hemiacetal (vi) Oxime
(vii) Ketal (vii) Imine
(ix) 2,4-DNP-derivative (x) Schiff’s base
45. Name the following compounds according to IUPAC system of nomenclature:
(i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl
(iii) CH3CH=CHCHO (iv) CH3COCH2COCH3
(v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH
(vii) OHCC6H4CHO-p
46. Draw the structures of the following compounds.
(i) 3-Methylbutanal (ii) p-Nitropropiophenone
(iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-en-2-one
(v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid
(vii) p,p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid
47. Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give
also common names.
(i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2CH(CH3)CHO
(iii) CH3(CH2)5CHO (iv) Ph-CH=CH-CHO
CHO
(v) (vi) PhCOPh

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48. Draw structures of the following derivatives.
(i) The 2,4-dinitrophenylhydrazone of benzaldehyde
(ii) Cyclopropanone oxime
(iii) Acetaldehydedimethylacetal
(iv) The semicarbazone of cyclobutanone
(v) The ethylene ketal of hexan-3-one
(vi) The methyl hemiacetal of formaldehyde
49. Predict the products formed when cyclohexanecarbaldehyde reacts with following
reagents.
(i) PhMgBr and then H3O+ (ii) Tollens’ reagent
(iii) Semicarbazide and weak acid (iv) Excess ethanol and acid
(v) Zinc amalgam and dilute hydrochloric acid
50. Which of the following compounds would undergo aldol condensation, which the
Cannizzaro reaction and which neither? Write the structures of the expected products of
aldol condensation and Cannizzaro reaction.
(i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde
(iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone
(vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal
51. How will you convert ethanal into the following compounds?
(i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid
52. Write structural formulas and names of four possible aldol condensation products from
propanal and butanal. In each case, indicate which aldehyde acts as nucleophile and
which as electrophile.
53. An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative,
reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it
gives 1,2-benzenedicarboxylic acid. Identify the compound.
54. An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute
sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic
acid produced (B). (C) on dehydration gives but-1-ene. Write equations for the reactions
involved.
55. Arrange the following compounds in increasing order of their property as indicated:
(i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity
towards HCN)
(ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid
strength)
(iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid
(acid strength)
56. Give simple chemical tests to distinguish between the following pairs of compounds.
(i) Propanal and Propanone (ii) Acetophenone and Benzophenone
(iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate
(v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone
(vii) Ethanal and Propanal
57. How will you prepare the following compounds from benzene? You may use any inorganic
reagent and any organic reagent having not more than one carbon atom
(i) Methyl benzoate (ii) m-Nitrobenzoic acid

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(iii) p-Nitrobenzoic acid (iv) Phenylacetic acid
(v) p-Nitrobenzaldehyde.
58. 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-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone
(v) Benzaldehyde to Benzophenone (vi) Bromobenzene to 1-Phenylethanol
(vii) Benzaldehyde to 3-Phenylpropan-1-ol
(viii) Benazaldehyde to a-Hydroxyphenylacetic acid
(ix) Benzoic acid to m- Nitrobenzyl alcohol
59. Describe the following:
(i) Acetylation (ii) Cannizzaro reaction
(iii) Cross aldol condensation (iv) Decarboxylation
60. Complete each synthesis by giving missing starting material, reagent or products

61. Give plausible explanation for each of the following:

(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone
does not.
(ii) There are two –NH2 groups in semicarbazide. However, only one is involved in the
formation of semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the
presence of an acid catalyst, the water or the ester should be removed as soon as
it is formed.
62. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The
molecular mass of the compound is 86. It does not reduce Tollens’ reagent but forms an
addition compound with sodium hydrogensulphite and give positive iodoform test. On
vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of
the compound.
63. Although phenoxide ion has more number of resonating structures than carboxylate ion,
carboxylic acid is a stronger acid than phenol. Why?

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