ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

1. The enol form of acetone, after treatment with D2O, gives

(a) (b)

(c) (d)

2. on aldol condensation followed by heating gives

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

3. The acid produced (A) in the sequence given below is

(a) Succinic acid (b) Malonic acid (c) Oxalic acid (d) Maleic acid
4. Acetic acid is obtained when
(a) methyl alcohol is oxidized with potassium permanganate
(b) calcium acetate is distilled in the presence of calcium formate
(c) acetaldehyde is oxidized with potassium dichromate and sulphuric acid
(d) glycerol is heated with sulphuric acid
5. HCOONa X + H2 is
(a) Na2CO3 (b) CO2 (c) (COONa)2 (d) CO

6.

Which of the following is not a possible product?

(a) (b)

(c) (d)

7. A liquid was mixed with ethanol and a drop of concentrated H 2SO4 was added. A compound with a
fruity smell was formed. The liquid was
(a) CH3OH (b) HCHO (c) CH3COCH 3 (d) CH3COOH
8. In Cannizzaro reaction given below

2PhCHO PhCH2OH + PhCOO– the slowest step is

(a) The attack of at the carboxyl group
(b) the transfer of hydride to the carbonyl group
(c) the abstraction of proton from the carboxylic group
(d) the deprotonation of PhCH2OH
9. Identify ‘Z’ in the given reaction

(a) (b)

(c) (d)

10. Benzoic acid on reaction with thionyl chloride gives

(a) o-chlorobenzoic acid (b) benzaldehyde
(c) acetophenone (d) benzoyl chloride
11. Which of the following will neither undergo aldol condensation nor Cannizzaro reaction?
(a) Formaldehyde (b) Ethanal (c) Benzophenone (d) Acetophenone
12. Friedel – Craft acylation of benzene with benzoyl chloride gives
(a) C6H5COCH3 (b) CH3COCH3 (c) C6H5COC6H5 (d) None of these
13. The correct order of acidic strength of the following compounds is

(a) I > II > III > IV (b) III < IV < II < I
(c) II > III > IV > I (d) II < III < IV < I
14. Identify ‘X’.

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

15. Which of the following is the correct IUPAC name of the given compound?

(a) 6-Formyl-5-hydroxy-3-oxohexan-1-oic acid (b) 3-Hydroxy-5-oxo-1-formylheptan-7-oic acid

(c) 1-Formyl-2-hydroxy-4-oxohexan-5-oic acid (d) 5-Hydroxy-3-oxo-6-formylhexan-1-oic acid
16. Identify the product of the following reactions.

(a) HOOC(CH2)4COOH (b)

(c) CH3(CH2)4CH3 (d) OHC(CH2)4CHO

17. Acetic acid on heating with P2O5 gives
(a) phthalic acid (b) terephthalic acid (c) acetic anhydride (d) none of these
18. Arrange the following compounds in decreasing order of reactivity towards nucleophilic addition
reaction.
Diethylketone (I), Benzaldehyde (II), Propanal (III), Acetaldehyde (IV)
(a) I > II > III > IV (b) IV > III > II > I
(c) II > III > I > IV (d) IV > III > I > II
19. Which of the following is the reaction product of the given reaction?
(CH3)2CO + NH2NHCONH2 
(a) (CH3)2C = NCONHNH2 (b)

(c) (CH3)2C = NNHCONH2 (d) Both (b) and (c)

20. Carbonyl compounds undergo nucleophilic addition reaction because of
(a) non-polar carbonyl group (b) electromeric effect
(c) more stable anion with negative charge on oxygen atom (d) none of these
21. Match the List I with the List II and select the correct answer using the code given below the lists:
List I List II
(Acids) (IUPAC names)
P. Phthalic acid 1. Hexane-1, 6-dioic acid
Q. Oxalic acid 2. Benzene-1, 2-dicarboxylic acid
R. Succinic acid 3. Ethane-1, 2-dioic acid
S. Adipic acid 4. Butane-1, 4-dioic acid
P Q R S
(a) 1 2 3 4
(b) 2 4 1 3
(c) 2 3 4 1
(d) 4 3 2 1
22. Match the List I with the List II and select the correct answer using the code given below the lists:
List I List II
(Pair of compounds) (Tests to distinguish)
P. C6H5CHO, HCHO 1. NaHCO3
Q. HCOOH, HCHO 2. NaHSO3
R. CH3CHO, HCHO 3. Fehling’s test
S. CH3COCH3, 4. Iodoform test
(CH3)2CHCOCH(CH3)2
P Q R S
(a) 1 3 2 4
(b) 3 1 2 4
(c) 4 3 2 1
(d) 3 1 4 2
23. Aldol condensation between the compounds followed by dehydration gives methyl vinyl ketone. Then,
the compounds are
(a) HCHO and CH3COCH3 (b) HCHO and CH3CHO
(c) Two molecules of CH3CHO (d) Two molecules of CH3COCH3

24.

The compound X is
(a) CH3COOH (b) BrCH2COOH (c) (CH3CO)2O (d) OHC – COOH
25. What is the product in the reaction?

(a) Acetaldehyde (b) Acetic acid (c) Formic acid (d) Formaldehyde
26. The reaction of HCOOH with conc.H2SO4 gives
(a) CO2 (b) CO (c) oxalic acid (d) acetic acid
27. In a set of reactions, acetic acid yielded product D.

The structure of D would be

(a) (b)

(c) (d)

28. Two isomeric compounds A and B have the formula C 3H6Cl2. With aq. KOH solution A gives propional-
dehyde and B gives acetone. Then A and B are
(a) CH3 – CCl2 – CH3 and CH3 – CH2 – CHCl2 (b) CH3 – CHCl – CHCl2 and CH3 – CH2 – CHCl2
(c) CH3 – CH2 – CHCl2 and CH3 – CCl2 – CH3 (d) CH3 – CHCl – CHCl2 and CH3 – CCl2 – CH3
29. End product of the following sequence of reaction is

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

30. On vigorous oxidation by permanganate solution,

(CH3)2C = CH – CH2 – CH3 gives

(a) (b)

(c) (d)

31. The correct product of the following sequence of reactions is

(a) (CH3)2CHCHBrCOOH (b) (CH3)2CHCH2COOH

(c) (CH3)2CHCH2CH2NH2 (d) (CH3)2C = CHCOOH
32. Which of the following combinations of reagents can bring about the given transformation?

(a) (b)

(c) (d) NaOH/Mg/ether, CO2, H2O/H+, CH3I

33. The strongest acid amongst the following compound is
(a) CH3COOH (b) HCOOH
(c) CH3CH2CH(Cl)CO2H (d) ClCH2CH2CH2COOH
34. Silver mirror test is given by which one of the following compounds?
(a) Acetaldehyde (b) Acetone (c) Butanoic acid (d) Benzophenone

35.

Products of the above reaction contain

(a) (b)

(c) (d) both (a) and (b)

36. Which catalyst is used for the reduction of methanal to methanol?
(a) Pyridine (b) Pd (c) V2O5 (d) K2Cr2O7
37. A colourless, pungent smelling liquid is strongly acidic to litmus. This is readily oxidized by KMnO 4 but
reduces mercuric chloride to mercurous chloride. Heating the original substance with excess of sulphuric
acid produces water and carbon monoxide. Give the structural formula of the compound.
(a) HCOOH (b) CH3COOH (c) (COOH)2 (d) both (a) & (c)
38. Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the
presence of
(a) a vinyl group (b) an isopropyl group
(c) an acetylene triple bond (d) two ethylenic double bonds
39. Which of the following acids will undergo HVZ reaction?
(a) CH3CH = CHCOOH (b) CH3CH2CBr2COOH
(c) C6H5COOH (d)

40. The order of reactivity of the following compounds is

(a) (i) > (ii) > (iii) > (iv) (b) (i) > (iii) > (iv) > (ii)
(c) (iii) > (i) > (iv) > (ii) (d) (ii) > (iv) > (iii) > (i)
41. Identify the reagent X in the following reaction.

CH3CH2C  N CH3CH2CHO
(a) LiAlH4/ether (b) H2/Pd-BaSO4
(c) SnCl2/HCl/H2O, boil (d) NaBH4/ether/H3O+
42. Hydrolysis of an ester is carried out in
(a) basic medium (b) acidic medium
(c) both (a) and (b) (d) neither (a) nor (b)
43. The oxidation of alcohols involves formation of carbon-oxygen double bond with the cleavage of
(a) O – H bond (b) C – H bond
(c) both O – H and C – H bond (d) neither O – H nor C – H bond
44. An organic compound with the molecular formula, C 9H10O forms 2, 4-DNP derivative, reduces Tollens’
reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives benzene-1, 2 dicarboxylic
acid. Identify the compound.

(a) (b)

(c) (d)
45. In a set of reactions m-bromobenzoic acid gave a product S. Identify the product S.

(a) (b)

(c) (d)

ANSWER KEY

1 2 3 4 5 6 7 8 9 10
b c a c c b d b c d
11 12 13 14 15 16 17 18 19 20
c c c c a a c d c c
21 22 23 24 25 26 27 28 29 30
c d a c b b a c b d
31 32 33 34 35 36 37 38 39 40
b a c a d b a a d b
41 42 43 44 45
c c c c d