26 Chapter

ALDEHYDES, KETONES AND

CARBOXYLIC ACIDS

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Analysis of NEET and AIIMS (Year 2010-2018)

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2
1
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2010 2011 2012 2013 2014 2015 2016 2017 2018
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Analysis of JEE Main and BITSAT (Year 2010-2018)

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NEET 4 Nucleophilic addition reactions of
AIIMS 3 aldehydes and ketones, chemical 4/5 9
JEE Main 3 reactions of aldehydes and ketones,
Carboxylic acids and its derivatives.
BITSAT 2
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ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 365
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Exercise 1 : Topic-wise MCQs

Topic 1: Nomenclature and Structure of Carbonyl Group 7. IUPAC name of the following compound is
O
1. Choose the correct IUPAC name for
CH3 - C H - CHO H
|
CH2 -CH 3
(a) Butan - 2- aldehyde (a) 2-(2-propenyl) butanal
(b) 2- methylbutanal (b) 2-(1-propenyl) butanal
(c) 3- methylisobutyraldehyde (c) 4-formyl 4-ethyl but-2-ene
(d) 2- ethylpropanal (d) 2-ethyl pent-3-en-l-al
2. The IUPAC name of CH3COCH(CH3)2 is
(a) 2-methyl-3-butanone Topic 2: Preparation of Aldehydes and Ketones
(b) 4-methylisopropyl ketone
(c) 3-methyl-2-butanone 8. Which alkene on ozonolysis gives CH3CH2CHO and
(d) Isopropylmethyl ketone CH3CCH3
3. IUPAC name of following will be ||
O
CHO
CH3
CH3 (a) CH3CH2CH = C (b) CH3CH2CH = CHCH2CH3
CH3
(c) CH3CH2CH = CH CH3 (d) CH 3 - C = CHCH 3
|
CH3
OH 9. An aldehyde group can be present
(a) 4-formyl 3-methyl 1-hydroxy benzene
(a) in between carbon chain
(b) 4-formyl 3-methyl phenol
(b) at any position in carbon atom
(c) 4-hydroxy 2-methyl benzaldehyde
(c) only at the end of carbon chain
(d) 4-hydroxy 2-methyl carbaldehyde
4. In > C = O group sigma bond is formed by (d) at the second carbon atom of the carbon chain
(a) sp2-p-overlapping (b) sp3-p-overlapping 10. Benzaldehyde is obtained from Rosenmund’s reduction of
(c) sp-p-overlapping (d) s-p-overlapping O O
5. Which of the following is correct for carbonyl compounds?
(a) CH3 (b) X
R R d+ d–
d– d+
(a) C=O (b) C=O
R¢ R¢ O
Cl
(c) d+ d– (d) d+ d–
(c) Cl (d) OH
R–C=O R–C=O

R¢ R¢ 11. Product of the following reaction is

6. Match the columns CN
Column-I Column-II SnCl +HCl
+ 2(H) ¾¾¾¾®
2
?
(Common names) (IUPAC names) H O+ 3
(A) Cinnamaldehyde (p) Pentanal
(B) Acetophenone (q) Prop-2-enal COOH CHO
(C) Valeraldehyde (r) 4-Methylpent-3-en-2-one (a) (b)
(D) Acrolein (s) 3-Phenylprop-2-enal
(E) Mesityl oxide (t) 1-Phenylethanone
O
(a) A – (s), B – (t), C – (p), D – (q), E – (r)
NH2
(b) A – (p), B – (q), C – (s), D – (t), E – (r) C ¾ CH3
(c) A – (t), B – (s), C – (p), D – (r), E – (q) (c) (d)
(d) A – (q), B – (t), C – (r), D – (s), E – (p)
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 367

12. Find out B in the given reactions 19. Product of the following reaction is
CN MgX
AlCl3 CrO 3 in (CH 3CO) 2O
+ CH 3 – X A B dry ether
H3O+ +
+
H3O
(a) acetophenone
O
(b) benzaldehyde
(c) cyclohexyl carbaldehyde
(d) benzoic acid (a) (b) OH
13. The reaction
CHO O
AlCl3
+ CO + HCl ¾¾¾®

(c) (d)
(a) Rosenmund’s reaction (b) Stephen’s reaction
(c) Cannizzaro’s reaction (d) Gatterman-Koch reaction
14. Which aldehyde cannot be obtained by Rosenmund’s Topic 3: Physical Properties
reaction? 20. Propanal and propanone, both have same molecular
(a) CH3CHO (b) HCHO formula(C3H6O), what do you expect about their boiling
(c) CH3CH2CHO (d) All of these points?
15. The conversion PhCN ® PhCOCH 3 , can be achieved (a) Both have same boiling point
most conveniently by reaction with (b) Boiling point of propanal is higher than the boiling
point of propanone.
(a) CH3MgBr followed by hydrolysis
(c) Boiling point of propanal is lower than the boiling point
(b) I2 – NaOH, CH3I
of propanone
(c) Dil. H2SO4 followed by reaction with CH2N2 (d) Nothing can be predicted
(d) LiAlH4 followed by reaction with CH3I 21. Assertion : The boiling points of aldehydes and ketones
16. Which of the following is used to prepare ketone in good are higher than hydrocarbons and ethers of comparable
yield from acyl chloride ? molecular masses.
(a) R-MgX (b) R2Cd Reason : There is a weak molecular association in aldehydes
(c) CO + HCl (d) CrO3 and ketones arising out of the dipole-dipole interactions.
17. In the given reaction (a) Assertion is correct, reason is correct; reason is a
CH3 CHO correct explanation for assertion.
Cl2/hu H2O (b) Assertion is correct, reason is correct; reason is not a
A correct explanation for assertion.
373K
(c) Assertion is correct, reason is incorrect.
A is (d) Assertion is incorrect, reason is correct.
CH2Cl CHCl2 22. The boiling points of aldehydes and ketones lie in between
(a) (b) alkanes and alcohols of comparable masses because
(a) alkanes are polar
(b) aldehydes and ketones are non-polar
CCl3 CH3 (c) alkanes are polar and aldehydes and ketones contain
(c) (d)
Cl C = O group and lower alcohols have H-
polar
18. Which of the following statement(s) is/are true regarding
preparation of aldehydes and ketones? bonding.
(i) Both can be prepared by the oxidation of the concerned (d) alkanes are held together by weak van der Waal’s
alcohol with copper at about 250ºC. forces (being polar), aldehydes and ketones contain
(ii) Both can be prepared by the oxidation of the concerned
alcohol by Oppenauer oxidation. C = O group and held together by strong
polar
(iii) Both can be prepared by the oxidation of respective
alcohol with acidic dichromate.
dipole-dipole attraction and lower alcohols have H-
(a) (i) only (b) (ii) and (iii) bonding, which is stronger than dipole-dipole
(c) (i) and (iii) (d) All the three attraction.
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34. A compound does not react with 2, 4-dinitrophenylhydrazine,

Topic 4: Chemical Reactions
the compound is :
23. Less reactivity of ketone is due to (a) Acetone (b) Acetaldehdye
(a) + I inductive effect decreases positive charge on (c) CH3OH (d) CH3CH2COCH3
carbonyl carbon atom 35. Which gives lactic acid on hydrolysis after reacting with
(b) steric effect of two bulky alkyl groups HCN ?
(c) sp2 hybridised carbon atom of carbonyl carbon atom (a) HCHO (b) CH3CHO
(d) Both (a) and (b) (c) C6H5CHO (d) CH3COCH3
24. Which of the following statement is false ? 36. The most appropriate reagent to distinguish between
(a) Cannizzaro reaction is given by aldehydes in presence acetaldehyde and formaldehyde is :
of alkali (a) Fehling’s solution
(b) Aldol condensation is given by aldehydes in presence (b) Tollen’s reagent
of alkali (c) Schiff’s reagent
(c) Aldol condensation is given by aldehydes and ketones (d) Iodine in presence of base
in presence of acids 37. 2-Pentanone and 3-pentanone can be distinguished by :
(d) None of the above (a) Cannizzaro's reaction (b) Aldol condensation
25. If formaldehyde and KOH are heated, then we get (c) Iodoform reaction (d) Clemmensen's reduction
(a) methane (b) methyl alcohol 38. Cross aldol condensation occurs between
(c) ethyl formate (d) acetylene (a) two same aldehydes
26. The reagent which can be used to distinguish acetophenone (b) two same ketones
from benzophenone is (c) two different aldehydes and ketones
(a) 2,4- dinitrophenylhydrazine (d) None of these
(b) aqueous solution of NaHSO3 39. Ketone upon treatment with Grignard reagent gives
(c) benedict reagent (a) primary alcohol (b) secondary alcohol
(d) I2and Na2CO3 (c) tertiary alcohol (d) aldehyde
27. Benzaldehyde reacts with ethanoic KCN to give 40. When acetaldehyde reacts with alcohol then produce
(a) C6H5CHOHCN (b) C6H5CHOHCOC6H5 (a) Acetal (b) Ketal (c) Acetone (d) None
(c) C6H5CHOHCOOH (d) C6H5CHOHCHOHC6H5 41. The product formed in Aldol condensation is
28. Acetaldehyde reacts with semicarbazide and forms (a) a beta-hydroxy aldehyde or a beta-hydroxy ketone
semicarbazone. Its structure is (b) an alpha-hydroxy aldehyde or ketone
(a) CH3CH = NNHCON = CHCH3 (c) an alpha, beta unsaturated ester
(b) CH3CH = NNHCONH2 (d) a beta-hydroxy acid
42. Which of the following products is formed when
(c) CH 3 CH = N — N — CONH 2 benzaldehyde is treated with CH3MgBr and the addition
|
OH product so obtained is subjected to acid hydrolysis ?
(d) CH3CH = N—CONHNH2 (a) A secondary alcohol (b) A primary alcohol
29. Iodoform test is not given by (c) Phenol (d) tert-Butyl alcohol
43. During reduction of aldehydes with hydrazine and
(a) 2-Pentanone (b) Ethanol
potassium hydroxide, the first step is the formation of
(c) Ethanal (d) 3-Pentanone
30. Phenylmethyl ketone can be converted into ethylbenzene (a) R — CH — — N — NH 2 (b) R — C º N
in one step by which of the following reagents? (c) R — C— NH 2 (d) R — CH— — NH
||
(a) LiAlH4 (b) Zn-Hg/HCl O
(c) NaBH4 (d) CH3MgI 44. A and B in the following reactions are
31. Which of the following compound will show positive silver OH
HCN B
mirror test ? R–C–R' KCN A R– C
(a) HCOOH (b) CH3(CHOH)3CHO R' CH2NH2
O
(c) CH3CO(CHOH)CH3 (d) Both (a) and (b) CN
32. Aldehydes and ketones are distinguished by which of the (a) A = RR'C , B = LiAlH4
following test ? OH
(a) Lucas test OH
(b) Tollen’s test (b) A = RR'C , B = NH3
(c) KMnO4 solution (Baeyer’s test) COOH
(d) None of these CN
33. In which reaction, > C = O can be reduced to > CH2? (c) A = RR'C , B = H 3O Å
(a) Wolf-Kishner reaction (b) Reimer-Tiemann reaction OH
(c) Wurtz reaction (d) None of these (d) A = RR'CH2CN, B = NaOH
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 369

45. Which one gives positive iodoform test ? X

55. C6H5CH=CHCHO ¾¾® C6H5CH=CHCH2OH
(a) (CH 3 ) 2 CHCH 2 OH In the above sequence X can be :
(b) C 6 H 5 - OH (a) H2/Ni (b) NaBH4
H (c) K2Cr2O7/H+ (d) Both (a) and (b)
| 56. Two compounds benzyl alcohol and benzoic acid are formed
(c) CH 3 - CH 2 - C - CH 2 - CH 3 from a compound, when it is heated in the presence of
| conc.NaOH, this compound is.
OH
(a) Benzaldehyde (b) Benzylalcohol
(d) CH 3CH 2 OH
(c) Acetophenone (d) Benzophenone
46. The compound that neither forms semicarbazone nor oxime 57. Which of the following compounds will give butanone on
is oxidation with alkaline KMnO4 solution?
(a) HCHO (b) CH3COCH2Cl (a) Butan-1-ol (b) Butan-2-ol
(c) CH3CHO (d) CH3CONHCH3
(c) Both of these (d) None of these
47. Schiff’s reagent gives pink colour with
58. Read the following statements and choose the correct option
(a) acetaldehyde (b) acetone
(c) acetic acid (d) methyl acetate (i) The carbonyl carbon atom is sp2 -hybridised
48. Benzophenone can be converted into benzene by using (ii) The carbonyl carbon is an electrophilic (Lewis acid)
(a) fused alkali centre
(b) anhydrous AlCl3 (iii) The carbonyl oxygen is a nucleophilic (Lewis base)
(c) sodium amalgam in water centre
(d) acidified dichromate (iv) Carbonyl compounds are non- polar in nature.
49. In the reaction of NaHSO3 with carbonyl compounds to (a) (i), (ii) and (iv) are correct
form bisulphite product, the nucleophile is (b) (i), (ii) and (iii) are correct
(a) HSO3– (b) SO3Na (c) (ii), (iii) and (iv) are correct
(c) SO3– – (d) None of the above
(d) (ii) and (iv) are correct
50. Wolf-Kishner reduction is
(a) reduction of carbonyl compound into alcohol 59. Aldehydes are generally more reactive than ketones in
(b) reduction of carbonyl compound into alkene nucleophilic addition reactions. Which of the following
(c) reduction of carboxyl compound into alkane statements accounts for this ?
(d) reduction of nitro compound into aniline (i) Sterically, the presence of two relatively large
substituents in ketones hinders the approach of
R OR nucleophile to carbonyl carbon
51. Compound of general formula C are called (ii) Aldehydes show resonance whereas ketones do not
(iii) Electronically, the presence of two alkyl groups reduce
H OR
the electrophilicity of the carbonyl carbon more
(a) diester (b) acid anhydride effectively.
(c) hemiacetal (d) acetal (iv) Electronically carbonyl carbon atom in ketones is more
52. Imine derivatives of aldehyde and ketone is called as electrophilic than in aldehydes
(a) Schiff’s reagent (b) Fehling’s reagent (a) (i) and (iii) (b) (i) and (iv)
(c) Schiff’s base (d) Schiff’s acid (c) (ii) and (iii) (d) (ii) and (iv)
53. Which reaction is used for detecting the presence of
OH -
carbonyl group? 60. 2C6 H5CHO ¾¾¾® C6 H5CH 2OH + C6 H5COO -
(a) Reaction with hydrazine H 2O
(b) Reaction with phenylhydrazine Which of the following statements are correct regarding the
(c) Reaction with hydroxylamine above reduction of benzaldehyde to benzyl alcohol?
(d) All of the above (i) One hydrogen is coming from H2O as H+ and another
54. The difference between aldol condensation and from C6H5CHO as H–
Cannizzaro’s reaction is that: (ii) One hydrogen is coming from H2O as H– and another
(a) the former takes place in aldehydes having no from C6H5CHO as H+
a-H-atom. (iii) One hydrogen from H2O and another from C6H5CHO,
(b) the former takes place in aldehydes having no both in the form of H–
a-H-atom. (iv) The reduction is an example of disproportionation
(c) the former takes place in aldehydes having no reaction
b-H-atom. (a) (i), (ii) and (iii) (b) (i) and (iv)
(d) none of the above (c) (ii), (iii) and (iv) (d) (iii) and (iv)
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61. Match the columns 66. Which of the following is an example of nucleophilic
Column-I Column-II addition ?
Zn - Hg / HCl O NNH 2
(A) R - CO - CH 3 ¾¾ ¾ ¾ ¾® (p) Friedel-Craft’s
|| NH 2 NH 2 ,H + ||
R - CH 2 - CH 3 reaction (a) C 6 H 5 C CH 3 ¾¾ ¾ ¾ ¾¾® C 6 H 5 C CH 3
NaOH
(B) 2C6 H5 CHO ¾¾¾® (q) Kolbe’s reaction O OH
|| |
C6 H5 COONa + C6 H5 CH 2 OH LiAlH
(b) C6 H 5 CCH 3 ¾¾¾¾
4 ® C H CHCH
6 5 3

(C) C6 H 6 + CH 3 COCl ¾¾¾¾

Anhyd.
® (r) Clemmensen’s (c) Both (a) and (b)
AlCl3 (d) None of the two
C6 H5 COCH3 reaction 67. Match the columns
(D) C 6 H 5 OH + CO 2 + NaOH ® (s) Cannizzaro’s Column-I Column-II
HOC6 H 4COONa reaction R
(A) C = NH (p) Oxime
(a) A – (p), B – (q), C – (r), D – (s) R
(b) A – (q), B – (p), C – (r), D – (s)
R
(c) A – (r), B – (s), C – (p), D – (q)
(B) C = NOH (q) Semicarbazone
(d) A – (s), B – (r), C – (p), D – (q) R
62. Match the columns
R
Column-I Column-II
(C) C = N – NH2 (r) Imine
(Reactions) (Reagents) R
(A) Benzophenone ® (p) LiAlH4
O
Diphenylmethane
R
(B) Benzaldehyde ® (q) DIBAL–H (D) C = N – NH – C – NH 2 (s) Hydrazone
1-Phenylethanol R
(C) Cyclohexanone ® (r) Zn(Hg)/conc. HCl (a) A – (q), B – (s), C – (p), D – (r)
Cyclohexanol (b) A – (r), B – (p), C– (s), D– (q)
(D) Phenyl benzoate ® (s) CH3MgBr (c) A – (r), B – (s), C – (p), D– (q)
Benzaldehyde
(d) A – (s), B – (r), C – (q), D– (p)
(a) A – (p), B – (s), C – (r), D – (q)
68. Acetal formation is a reversible reaction
(b) A – (q), B – (s), C – (p), D – (r)
+
(c) A – (s), B – (r), C – (q), D – (p) R H R OH R'OH, H +
C = O + R'OH C
(d) A – (r), B – (s), C – (p), D – (q) H H OR'
63. Observe the following structures and pick up the correct
statement. R OR'
+ H2O
C
+ H OR'
C=O C = OH Under what conditions, the reaction can be forced to proceed
I II only in right (forward) direction ?
(a) Carbonyl carbon of I is more electrophilic than that (a) Using excess of alcohol
of II (b) Using high temperature
(b) Carbonyl carbon of I is less electrophilic than that (c) Using dilute acid and excess of alcohol
of II (d) Using dry acid and excess of alcohol
(c) Carbonyl carbon of both structures have equal 69. In the crossed Cannizzaro reaction involving HCHO as one
electrophilic character of the components
(d) It depends upon the complete structure of the (a) HCHO is always oxidised because of electronic effect
compound (b) HCHO is always oxidised because of steric effect
64. Which of the following reagent reacts in different ways with (c) both of the above statements are true
CH3CHO, HCHO and C6H5CHO ?
(d) none of the above statement is true
(a) Fehling solution (b) C6H5NHNH2
70. When ethanal reacts with propanal in the presence of a
(c) Ammonia (d) HCl
base, the number of products formed is
65. A new carbon - carbon bond is formed in
(a) 2 (b) 3 (c) 4 (d) 5
(i) Aldol condensation (ii) Kolbe’s reaction
71. Which of the following compound will undergo self aldol
(iii) Reimer-Tiemann reaction
condensation in the presence of cold dilute alkali ?
(iv) Wurtz Fittig reaction
(a) (i) and (iii) (b) (ii) and (iii) (a) CH2=CH - CHO (b) CH º C - CHO
(c) (i), (ii) and (iiv) (d) All the four (c) C 6 H 5 CHO (d) CH 3 CH 2 CHO .
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 371

72. Identify X, undergoes Cannizzaro reaction but not aldol, then possible
H3C product due to nitration is
CH MgI (a) 3–nitroacetophenone
C = O ¾¾¾¾3 ® Intermediate ¾¾¾
H 2O
®X
H3C dry ether (b) (2–nitro)–2–phenylethanal
(c) (2–nitro)–1–phenylpropan–2–one
(a) CH3OH (b) Ethyl alcohol
(d) 3–nitrobezaldehyde
(c) Methyl cyanide (d) tert-Butyl alcohol
73. An organic compound of formula, C3H6O forms phenyl Topic 5: Nomenclature and Structure of Carboxyl Group
hydrazone, but gives negative Tollen’s test. The compound is
(a) CH3CH2COCH3 (b) CH3CH2CHO 81. Which of the following best represents the structure of the
(c) CH3COCH3 (d) Both (a) and (c) carboxylate ion ?
– –
R NH3 Hydrolysis d d
74. C = O HCN (A) (B) (C) O O
R
(a) R– C (b) R – C
Compound (C) in above reaction is
O O–
(a) a-hydroxy acid (b) a-amino acid d+ d
(c) a-amino alkanol (d) a-amino b-hydroxy acid
75. Benzaldehyde is less reactive than propanal because d+
(i) the carbon atom of the carbonyl group of benzaldehyde O
is less electrophilic as in propanal. (c) R– C (d) None of these
(ii) the carbon atom of the carbonyl group of benzaldehyde O
is more electrophilic as in propanal. d+
(iii) carbonyl group in benzaldehyde is more polar due to 82. Structure of the compound whose IUPAC name is 3-ethyl-
resonance 2-hydroxy-4-methylhex-3-en-5-ynoic acid is :
(iv) carbonyl group in benzaldehyde is less polar due to OH OH
resonance
(a) (i) and (iii) (b) (i) and (iv) (a) COOH (b) COOH
(c) (i) only (d) (iv) only
76. Addition of hydrogen cyanide to aldehydes and ketones
occurs in presence of a base.The role of base is to OH
(i) catalyse the reaction COOH
(ii) generate CN– ion (c) (d) COOH
(iii) slow down the reaction OH
(iv) to stabilize the cyanohydrins
83. Match the columns
(a) (i) and (iii) (b) (i) and (ii)
Column-I Column-II
(c) (i) and (iv) (d) (ii) and (iv)
77. When benzaldehyde and acetaldehyde undergoes reaction COOH
with the 2, 4–DNP ? (A) CH2 (p) Glutaric acid
(a) Benzaldehyde reacts slowly than acetaldehyde COOH
(b) Acetaldehyde reacts slowly than benzaldehyde
(c) Both reacts equally CH2 COOH
(d) Both do not react with 2, 4-DNP (B) (q) Adipic acid
78. Suppose the reaction of compound containing ketone as CH2 COOH
functional group is carried in basic medium of NaOH. Which
(C) CH2 COOH (r) Succinic acid
of the following will one use to protect the unwanted reaction
due to presence of carbonyl moiety?
CH2
(a) NaHSO3
(b) HCN
CH2 COOH
(c) ethylene glycol and HCl
(d) None of these
79. A compound C5H10O forms orange–red precipitate upon (D) CH2 COOH (s) Malonic acid
reaction with 2,4–DNP, but does not give positive Tollen’s
test and iodoform test. Possible compound is CH2
(a) 2, 2–dimethylpropanal (b) 3–methylbutan–2–one
(c) Pentan–3–one (d) None of the above CH2
80. Nitration of the compound is carried out, this compound
gives red–orange ppt. with 2,4–DNP, this compound CH2 COOH
 EBD_7374
372 CHEMISTRY

(a) A – (q), B – (p), C – (s), D – (r) 88. In the given reaction,

(b) A – (r), B – (p), C – (s), D – (q) H O
2 ®I
(C6 H5 CO) 2 O ¾¾¾
(c) A – (s), B – (r), C – (p), D – (q)
H O
2 ® II
(d) A – (r), B – (q), C – (s), D – (p) C6 H 5 COOCOCH 3 ¾¾¾
Identify the product(s) formed in the given reaction.
Topic 6: Methods of Preparation of Carboxylic Acids I II
(a) 2 molecules of benzoic acid 2 molecules of ethanoic acid
84. R HCl gas R O CH2 (b) 2 molecules of benzoic acid 1 molecule of benzoic acid
C = O +A C + H2O and 1 molecule of ethanoic acid
R dil HCl R O CH2 (c) 1 molecule of ethanoic acid 1 molecule of benzoic acid
A is (d) 1 molecule of benzoic acid 1 molecule of butanoic acid
(a) CH3OH (b) CH3COOH 89. Select the acid(s) which cannot be prepared by Grignard
CH 2COOH CH 2OH reagent.
(c) (d) (a) Acetic acid (b) Succinic acid
CH 2COOH CH2OH (c) Formic acid (d) All of the above
90. Through which of the following reactions number of carbon
85. Which of the following can not be oxidised to give carboxylic
atoms can be increased in the chain?
acid?
(i) Grignard reaction (ii) Cannizzaro’s reaction
CH2CH2CH3 (iii) Aldol condensation (iv) HVZ reaction
CH3 Choose the correct option.
(a) (a) Only (iii) and (i) (b) Only (iii) and (ii)
(b)
(c) Only (iii) and (iv) (d) (i), (ii), (iii) and (iv)
K 2Cr2O 7+H2SO4
CH3 91. Z. Here Z is
CH3
HC CH3 C CH3
CH3 (a) HOOC
(c) (d) (b) (CH3)3CCOOH
(c) Both (a) and (b)
86. MgBr (d) HOOC COOH

(i) CO Topic 7: Physical Properties

¾¾¾¾
2®
P
(ii) H 3O Å
92. Lower carboxylic acids are soluble in water due to
(a) low molecular weight (b) hydrogen bonding
In the above reaction product 'P' is
(c) dissociation into ions (d) easy hydrolysis
CHO COOH 93. Dimerisation of carboxylic acids is due to
(a) ionic bond
(b) covalent bond
(a) (b) (c) coordinate bond
(d) intermolecular hydrogen bond
94. Boiling points of carboxylic acids are
OH (a) lower than corresponding alcohols
O (b) higher than corresponding alcohols
|| (c) equal to that of corresponding alcohols
(c) (d) C6 H5 - C - C 6 H5 (d) None of the above
Topic 8: Chemical Reaction
87. The end product B in the sequence of reactions, 95. In the anion HCOO– the two carbon-oxygen bonds are found
-
CN
R - X ¾¾¾® A ¾¾¾¾
® B is
NaOH to be of equal length. What is the reason for it?
(a) Electronic orbitals of carbon atom are hybridised
(a) an alkane (b) The C=O bond is weaker than the C–C bond
(b) a carboxylic acid (c) The anion HCOO– has two reasonating structures
(c) sodium salt of carboxylic acid (d) The anion is obtained by removal of a proton from the
(d) a ketone acid molecule
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 373

96. Carboxylic acids are more acidic than phenol and alcohol 107. Which of the following statements are false?
because of (i) No aldehyde can be prepared by the oxidation of primary
(a) intermolecular hydrogen bonding alcohol with acidic KMnO4.
(b) formation of dimers (ii) Aldehydes having a boiling point less than 100°C can
(c) highly acidic hydrogen be prepared by the oxidation of primary alcohol with
(d) resonance stabilization of their conjugate base acidic dichromate.
97. Which of the following has the maximum acidic strength ? (iii) Secondary alcohols on oxidation with PCC in
(a) o-nitrobenzoic acid (b) m-nitrobenzoic acid dichloromethane give carboxylic acids having lesser
(c) p-nitrobenzoic acid (d) p-nitrophenol number of carbon atoms
98. Which one of the following esters is obtained by the (iv) Tertiary alcohols can't be oxidised at all
esterification of propan-2-ol with ethanoic acid ? (a) (ii) and (iii) (b) (ii), (iii) and (iv)
(a) (CH3)2CHCOOCH3 (b) CH3COOCH2CH3 (c) (i), (iii) and (iv) (d) (i), (ii) and (iii)
(c) CH3COOCH(CH3)2 (d) (CH3)2CHCOOCH2CH3 108. Which of the following statement(s) is/are true regarding
99. Among the following acids which has the lowest pK a esterification of a carboxylic acid with an alcohol ?
(i) It is carried out in presence of a strong acid which acts
value?
as a catalyst.
(a) CH 3 CH 2 COOH (b) (CH3 ) 2 CH - COOH
(ii) The strong acid makes the carbonyl carbon more
(c) HCOOH (d) CH 3COOH electrophilic, and hence causes the alcohol, a strong
100. Which reagent can convert acetic acid into ethanol ? nucleophile to attack on the carbonyl carbon.
(a) Na + alcohol (b) LiAIH4 + ether (iii) The strong acid makes the carbonyl group more
(c) H2 + Pt (d) Sn + HCl electrophilic which is thus attacked easily by an
101. Benzoic acid may be converted to ethyl benzoate by reaction alcohol, a weak nucleophile.
with (iv) Esterification can be done even in absence of a strong
(a) sodium ethoxide (b) ethyl chloride acid.
(c) dry HCl—C2H5OH (d) ethanol (a) (i) and (ii) (b) (i) and (iii)
102. Benzoic acid reacts with conc. HNO3 and H2SO4 to give : (c) (i) only (d) (iv) only
(a) 3-Nitrobenzoic acid 109. Assertion : Compounds containing –CHO group are easily
(b) 4-Benzene sulphonic acid oxidised to corresponding carboxylic acids.
(c) 4-Nitrobenzoic acid Reason : Carboxylic acids can be reduced to alcohols by
(d) 2-Nitrobenzoic acid treatment with LiAlH4.
103. The yield of ester in esterification can be increased by (a) Assertion is correct, reason is correct; reason is a
CH 3 CH 2 OH + CH 3COOH ‡ˆˆ ˆˆ† correct explanation for assertion.
CH3COOCH2CH3 + H 2O (b) Assertion is correct, reason is correct; reason is not a
(a) removing water correct explanation for assertion.
(b) taking ethanol in excess (c) Assertion is correct, reason is incorrect.
(c) taking acetic acid in excess (d) Assertion is incorrect, reason is correct.
(d) all the above factors 110. Which of the following is the correct decreasing order of
104. A carboxylic acid can best be converted into acid chloride acidic strength of
by using (i) Methanoic acid (ii) Ethanoic acid
(a) PCl5 (b) SOCl2 (iii) Propanoic acid (iv) Butanoic acid
(c) HCl (d) ClCOCOCl (a) (i) > (ii) > (iii) > (iv) (b) (ii) > (iii) > (iv) > (i)
105. The strongest acid among the following is – (c) (i) > (iv) > (iii) > (ii) (d) (iv) > (i) > (iii) > (ii)
(a) Salicylic acid (b) m-hydroxybenzoic acid 111. Ethanoic acid can’t be obtained by which of the following
(c) p-hydroxybenzoic acid (d) Benzoic acid reaction ?
106. Arrange the following carboxylic acid in their decreasing (i) KCN
(i) C2 H5Cl ¾¾¾¾¾
+®
acidity. (ii) H3O

1. COOH Oxalic acid (ii)

(i) AgCN
CH3Cl ¾¾¾¾¾ ®
+
(ii) H3O
COOH KMnO / OH -
2. HOOC – CH2 – COOH Malonic acid (iii) CH 3CH = CH 2 ¾¾¾¾¾¾
4 ®
heat
3. CH2– COOH Succinic acid (i) Mg
(iv) CH3Br ¾¾¾¾¾
®
(ii) CO2
CH2– COOH (iii) H3O +

(a) 3 > 2 > 1 (b) 1 > 2 > 3 (a) (iii) and (iv) (b) (i) and (ii)
(c) 2 > 3 > 1 (d) 2 > 1 > 3 (c) (ii) and (iii) (d) (i) and (iv)
 EBD_7374
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112. In a set of the given reactions, acetic acid yielded a (a) FCH 2 COOH > CH 3COOH > BrCH 2 COOH >
product C. ClCH2COOH
CH C H Br (b) BrCH2COOH > ClCH2COOH > FCH2COOH > CH3COOH
CH3 COOH + PCl5 ¾¾
® A ¾¾¾®
6 6
Anh.AlCl
B ¾¾¾¾
2 5 ®C
(c) FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
3 Ether
(d) CH3 COOH > BrCH2 COOH > ClCH2COOH >
Product C would be FCH2COOH
C2 H 5 115. The correct order for the acidic character of the following
| carboxylic acids is
(a) CH 3 - C (OH)C 6 H 5 (b) CH 3 CH (OH) C 2 H 5
COOH
(c) CH 3 COC 6 H 5 (d) CH 3 CH (OH ) C 6 H 5 COOH COOH
113. Kolbe’s electrolytic method can be applied on OH

(i) CH 2 COONa (ii) CHCOONa

| || OH
I II
CH 2 COONa CHCOONa III
COOH COOH
(iii) C6 H5COOK (iv) CH3COOK CH3 HO OH
(a) (i), (ii) and (iv) (b) (i), (ii) and (iii)
(c) (ii), (iii) and (iv) (d) (iii) and (iv)
IV V
114. Which of the following represents the correct order of the (a) IV > I > II > III > V (b) V > II > III > I > IV
acidity in the given compounds? (c) V > II > IV > III > I (d) V > II > IV > I > III

Exercise 2 : Exemplar & Past Year MCQs

NCERT Exemplar MCQs 3. The correct order of increasing acidic strength is ........ .
(a) phenol < ethanol < chloroacetic acid < acetic acid
1. Addition of water to alkynes occurs in acidic medium and in
(b) ethanol < phenol < chloroacetic acid < acetic acid
the presence of Hg 2+ ions as a catalyst. Which of the
(c) ethanol < phenol < acetic acid < chloroacetic acid
following products will be formed on addition of water to
(d) chloroacetic acid < acetic acid < phenol < ethanol
but - 1-yne under these conditions?
O
O ||
|| 4. Compound Ph — O — C— Ph can be prepared by the
(a) CH 3 — CH 2 — CH 2 — C— H reactions of ............ .
(a) phenol and benzoic acid in the presence of NaOH
O
|| (b) phenol and benzoyl chloride in the presence of pyridine
(b ) CH3 — CH 2 — C — CH 3 (c) phenol and benzoyl chloride in the presence of ZnCl 2
(d) phenol and benzaldehyde in the presence of palladium
O 5. The reagent which does not react with both, acetone and
|| benzaldehyde?
(c) CH3 — CH 2 — C — OH + CO 2
(a) Sodium hydrogen sulphite
O O (b) Phenyl hydrazine
|| || (c) Fehling's solution
(d) CH 3 — C— OH + H — C— H (d) Grignard reagent
2. Which of the following compounds is most reactive towards 6. Cannizzaro's reaction is not given by ........ .
nucleophilic addition reactions? CHO
O O (a) (b) CHO
|| || CH3
(a) CH 3 — C — H (b) CH3 — C — CH 3 (c) HCHO (d) CH3CHO
7. Which product is formed when the compound
O O
|| ||
(c) —C—H (d) — C — CH 3 CHO is treated with concentrated aqueous KOH
solution?
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 375

+ – Past Year MCQs

(a) KO CHO
13. Which one is most reactive towards Nucleophilic addition
O reaction? [AIPMT 2014]
|| - +
(b) C– OK + CH2OH CHO COCH3
(a) (b)
O
+ – || - + + - – + CHO CHO
(c) KO C O K+ K O OK

(c) (d)
O
|| - + –+
(d) C— O K + OK CH3 NO2

40% H SO
14. Ethanoic acid on heating with ammonia forms compound A
8. CH3 — C º CH ¾¾¾¾¾®
2 4 A which on treatment with bromine and sodium hydroxide
1% HgSO 4
gives compound B. Compound B on treatment with NaNO2/
Isomerisation
¾¾¾¾¾¾ ® CH3 — C— CH3 dil. HCl gives compound C. The compounds A, B and C
|| respectively are [AIIMS 2014, S]
O
(a) ethanamide, methanamine, methanol
structure of 'A' and type of isomerism in the above reaction
are respectively (b) propanamide, ethanamine, ethanol
(a) Prop-1-en-2-ol, metamerism (c) N-ethylpropanamide, methaneisonitrile, methanamine
(b) Prop-1-en-1-ol, tautomerism (d) ethanamine, bromoethane, ethanedia-zonium chloride
(c) Prop-2-en-2-ol, geometrical isomerism CHO
(d) Prop -1-en-2-ol, tautomerism
9. Compounds A and C in following reaction are ........... . Dil. NaOH
15. + CH3CHO ¾¾¾¾¾
® A .
(Major)
(i ) CH MgBr H SO ,D
CH 3 CHO ¾¾¾¾¾¾
( )
3 ® ( A ) ¾¾¾¾¾
2 4 ® (B)
ii H 2O

Hydroboration oxidation
(A) will be – [AIIMS 2014, A]
¾¾¾¾¾¾¾¾¾® ( C )
OH
(a) identical (b) positional isomers |
(c) functional isomers (d) optical isomers (a) C6 H5 CH - CH 2CHO (b) C6H5CH = CH – CHO
10. Which is the most suitable reagent for the following
conversion? (c) C6H5CH2CH2CHO (d) Both (b) & (c)
16. Sodium phenoxide when heated with CO2 under pressure at
O 125ºC yields a product which on acetylation produces C.
||
CH3 — CH = CH — CH 2 — C— CH 3 ¾¾
® [JEE M 2014, S]
ONa 125° H+
O + CO2 ¾¾ ¾¾
5 Atm
® A ¾¾ ¾® C
Ac2 O
||
CH3 — CH = CH — CH 2 — C — OH The major product C would be
(a) Tollen's reagent (b) Benzoyl peroxide
(c) I2 and NaOH solution (d) Sn and NaOH solution OCOCH3 OH
11. Which of the following compounds will give butanone on COOH COCH3
oxidation with alkaline KMnO4 solution? (a) (b)
(a) Butan-1-ol (b) Butan-2-ol
(c) Both (a) and (b) (d) None of these COCH3
12. In Clemmensen reduction, carbonyl compounds is treated
with ......... . OH OCOCH3
(a) zinc amalgam + HCl
(b) sodium amalgam + HCl COOCH3
(c) (d)
(c) zinc amalgan + nitric acid COOH
(d) sodium amalgam + HNO3
 EBD_7374
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17. In the reaction, OCOCH3

LiAlH PCl alc.KOH (a)
CH 3 COOH ¾¾¾¾ 4 ® A ¾¾¾ 5 ® B ¾¾¾¾® C

the product C is: [JEE M 2014, S] ON

2
(a) Acetaldehyde (b) Acetylene OCOCH3
(c) Ethylene (d) Acetyl chloride
18. The correct order of decreasing acid strength of (b)
H CO
trichloroacetic acid (A), trifluoroacetic acid (B), acetic acid 3
(C) and formic acid (D) is : [BITSAT 2014, S] OCOCH3
(a) B > A > D > C (b) B > D > C > A (c)
(c) A > B > C > D (d) A > C > B > D
19. The reaction, [BITSAT 2014, S] OCOCH3
CO + H O
CH3 - CH = CH 2 ¾¾¾¾¾
2
® CH3- CH - CH 3 (d)
H+ |
COOH Cl
is known as 25. In a set of reactions m-bromobenzoic acid gave a product D.
(a) Wurtz reaction Identify the product D. [AIIMS 2015, S]
(b) Koch reaction
(c) Clemmensen reduction COOH
(d) Kolbe’s reaction SOCl2 NH3 NaOH
20. An organic compound 'X' having molecular formula C5H10O B C Br2
D
yields phenyl hydrazone and gives negative response to Br
the Iodoform test and Tollen's test. It produces n-pentane
on reduction. 'X' could be :- [AIPMT 2015, S] SO2NH2 COOH
(a) 2-pentanone (b) 3-pentanone (a) (b)
(c) n-amyl alcohol (d) pentanal
Br NH2

21. Treatment of cyclopentanone =O with methyl

NH2 CONH2
lithium gives which of the following species? (c) (d)
[AIPMT 2015, C]
Br Br
(a) Cyclopentanonyl cation
(b) Cyclopentanonyl radical 26. Assertion : Benzaldehyde is more reactive than ethanol
(c) Cyclopentanonyl biradical towards nucleophilic attack.
(d) Cyclopentanonyl anion Reason : The overall effect of –I and + R effect of phenyl
22. The enolic form of ethyl acetoacetate as below has: group decreases the electron density on the carbon atom of
> C = O group in benzaldehyde. [AIIMS 2014, 2015, C]
[AIPMT 2015, S]
(a) Assertion is correct, reason is correct; reason is a
H H2 correct explanation for assertion.
H3C C O H3C C O (b) Assertion is correct, reason is correct; reason is not a
C C C C
correct explanation for assertion.
OH OC2H5 O OC2H5 (c) Assertion is correct, reason is incorrect.
(d) Assertion is incorrect, reason is correct.
(a) 16 sigma bonds and 1 pi - bond 27. Which compound would give 5 - keto - 2 - methylhexanal
(b) 9 sigma bonds and 2 pi - bonds upon ozonolysis ? [JEE M 2015, S]
(c) 9 sigma bonds and 1 pi - bond CH3
(d) 18 sigma bonds and 2 pi - bonds CH3
23. Reaction of a carbonyl compound with one of the following
reagents involves nucleophilic addition followed by (a) (b) H3C
elimination of water. The reagent is : [AIPMT 2015 RS, A]
(a) a Grignard reagent CH3
(b) hydrazine in presence of feebly acidic solution CH3
(c) hydrocyanic acid CH3
(d) sodium hydrogen sulphite
(c) CH3 (d)
24. Which one of the following esters gets hydrolysed most
easily under alkaline conditions? [AIPMT 2015 RS, A] CH3
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 377

28. The correct statement regarding a carbonyl compound with

a hydrogen atom on its alphacarbon, is : [NEET 2016, C] (c) and
(a) a carbonyl compound with a hydrogen atom on its alpha-
carbon never equilibrates with its corresponding enol.
(b) a carbonyl compound with a hydrgen atom on its alpha-
carbon rapidly equilibrates with its corresponding enol
and this process is known as aldehyde-ketone
(d) and
equilibration.
(c) a carbonyl compound with a hydrogen atom on its
alpha-carbon rapidly equilibrates with its
corresponding enol and this process is known as
carbonylation.
33. Consider the reactions :- [NEET 2017, A]
(d) a carbonyl compound with a hydrogen atom on its
alpha-carbon rapidly equilibrates with its Cu [Ag(NH3)2]
+

corresponding enol and this process is known as keto- X A Silver mirror

573K – OH/D
enol tautomerism. (C2H6O) observed
– OH/D
29. The product formed by the reaction of an aldehyde with a Y
O
primary amine is [NEET 2016, A]
(a) schiff base (b) ketone Nh2 – NH – C – NH2
(c) carboxylic acid (d) aromatic acid Z
30. Aldehydes that do not undergo aldol condensation are Identify A, X, Y and Z
[AIIMS 2016, C] (a) A-Methoxymethane, X-Ethanol, Y-Ethanoic acid, Z-
1. propanal 2. trichloroethanal Semicarbazide.
3. methanal 4. ethanal (b) A-Ethanal, X-Ethanol, Y-But-2-enal, Z-Semicarbazone
5. benzaldehyde (c) A-Ethanol, X-Acetaldehyde, Y- Butanone, Z- Hydrazone
(a) 3 and 4 only (b) 3 and 5 only (d) A-Methoxymethane, X-Ethanoic acid, Y-Acetate ion,
(c) 1, 2 and 3 only (d) 2, 3 and 5 only Z-hydrazine.
31. Assertion : The boiling points of aldehydes and ketones 34. Of the following, which is the product formed when
are higher than hydrocarbons and ethers of comparable cyclohexanone undergoes aldol condensation followed by
molecular masses. heating ? [NEET 2017, A]
Reason : There is a weak molecular association in aldehydes
and ketones arising out of the dipole-dipole interactions.
[AIIMS 2016, C] (a) (b)
(a) Assertion is correct, reason is correct; reason is a
correct explanation for assertion. O OH
(b) Assertion is correct, reason is correct; reason is not a
O
correct explanation for assertion.
(c) Assertion is correct, reason is incorrect.
(d) Assertion is incorrect, reason is correct. (c) (d)
32. The most likely acid-catalysed aldol condensation products
of each of the two aldehydes I and II will respectively be O O OH
[BITSAT 2016, S]
35. Aldol condensation will not be observed in
[AIIMS 2017, C]
CHO (I) and (II)
(a) chloral (b) phenylacetaldehyde
(c) hexanal (d) nitromethane
36. The reaction
(a) and
Red P
RCH 2 CH 2 COOH ¾¾¾® R - CH 2 - CH - COOH
Br2 |
Br
is called as [AIIMS 2013, 2017, C]
(a) Reimer- Tiemann reaction
(b) and (b) Hell-volhard Zelinsky reaction
(c) Cannizzaro reaction
(d) Sandmeyer reaction
 EBD_7374
378 CHEMISTRY

37. The correct sequence of reagents for the following

CH2 – OH CH2 – OH
conversion will be : [JEE M 2017, S]
(c) (d)
O HO CH3

CH2 – OH COOH

HO–CH3 O
CHO CH3
C – CH3
(a) [Ag(NH3)2]+ OH–, H+/CH3OH, CH3MgBr Br2
41. In the reaction ¾¾¾¾ ® product,
(b) CH3MgBr, H+/CH3OH, [Ag(NH3)2]+ OH– NaOH

(c) CH3MgBr, [Ag(NH3)2]+ OH–, H+/CH3OH

(d) [Ag(NH3)2]+ OH–, CH3MgBr, H+/CH3OH CH3
38. The major product obtained in the following reaction is : product is [AIIMS 2018, A]
O [JEE M 2017, S]
O O
O
C – CH2 – Br C – CH3
(a) (b)
DIBAL–H

CH3 CH2 – Br
COOH
OH O O
OH
C – CH3 Br C – CH3
(a) CHO (b) CHO (c) (d)
COOH
Br
CHO
CH3 CH3

CHO CH3
(c) (d) CHO | H2 /Pd
42. CH3– C = CH – CH2 – C – CH3 ¾¾¾¾ ®
COOH CHO ||
39. Carboxylic acids have higher boiling points than aldehydes, O
ketones and even alcohols of comparable molecular mass. No. of stereoisomers [AIIMS 2018, S]
It is due to their [NEET 2018, C] (a) 2 (b) 4 (c) 8 (d) 6
(a) Formation of intramolecular H-bonding O
(b) Formation of carboxylate ion
(c) Formation of intermolecular H-bonding 43. CH 3 NO 2
¾¾ ¾ ¾® [ A ] ¾
¾ ¾® [ B ]
(d) More extensive association of carboxylic acid via van C 2 H 5O -
der Waals force of attraction O
COOH
HONO
(i) B H ¾¾ ¾
¾®
40. ¾¾¾¾¾¾
2 6
® [AIIMS 2018, A] H+
(ii) DlBAL–H
(iii) H3OÅ Which reaction is/are involved in the above conversion?
CN [AIIMS 2018, S]
(a) Diazotisation and Beckmamn rearrangement
COOH CH2 – OH (b) Diazotisation and Robinson annulation
(a) (b) (c) Aldol condensation and diazotisation
(d) Diazotisation and pinacol type of rearrangement

CHO CHO
ALDEHYDES, KETONES AND CARBOXYLIC ACIDS 379

Exercise 3 : Try If You Can

1. When cylohexanone is treated with Na 2CO3 solution, we 7. Which of the following is an example of nucleophilic
get addition ?
O O O NNH 2
OH || NH NH ,H +
2 ¾2¾¾® C H C CH
||
(a) C 6 H 5 C CH 3 ¾¾ ¾ 6 5 3
(a) (b)
OH O OH
|| |
O (b) LiAlH 4
C 6 H 5 C CH 3 ¾¾ ¾¾® C 6 H 5 C HCH 3
OH
COOH (c) Both (a) and (b)
(c) (d) (d) None of the two
COOH
O
– ||
2. The reacion OH is an 4 ¾® Z ; Z is NH OH
O 8. CH 3 C C 2 H 5 + NaCN + NH 4 Cl ¾¾ ¾
O
CHO CH3 OH CH3 OH
example of C C
(a) (b)
(a) oxidation reaction (b) reduction C2H3 COOH C2H5 CN
(c) both (d) aldol condensation
3. When o-hydroxybenzaldehyde is heated with ethanoic CH3 NH2 CH3 CN
anhydride in presence sodium ethanoate, compound (c) C (d) C
C2H5 CN C2H5 COOH
formed during the reaction is
9. The compund having formula,
OH OH
O O
(a) (b) || ||
COOCH3 COOH CH 3 - C- CH 2 - C - OC 2 H 5
O O (a) forms dioxime
(c) (d) Both (b) and (c) (b) undergoes iodoform test
(c) both (a) and (b)
4. A new carbon - carbon bond is formed in (d) neither of the two
Aldol condensati on Kolbe' s reaction 10. Aldehydic group can be protected
I II (a) by acetal formation against alkaline oxidising agents.
Reimer - Tiemann reaction Wurtz Fittig reaction (b) by mercaptal formation against acidic oxidising agents
III IV (c) both (a) and (b)
(a) I, III (b) II, III (d) None of the above
(c) I, III, IV (d) All the four O
5. The correct stability order of the following three quinones +
H
is 11. X , most likely the compound X is
O O
O R R
O O OH OH

O (a) (b)
I II III R
R R R
(a) I > III > II (b) I = III > II
OH OH
(c) I = II > III (d) III > I > II
R R
OH - ,Cl R
6. CH 3 COCH 2 Cl ¾¾¾¾¾2®
Product P is (c) (d)
(a) ClCH2COCH2Cl (b) CH3COCHCl2
(c) both (a) and (b) (d) ClCH2COOH+CH3Cl R
 EBD_7374
380 CHEMISTRY

Ca(OH) COOH COOH

12. CH 3CHO + 4HCHO ¾¾¾¾2¾
®

1
C(CH 2 OH) 4 + (HCOO) 2 Ca (c) (d)
2
Cl
the above reaction is an example of
(a) aldol condensation Cl
(b) Cannizzaro reaction 14. Which of the followng acts as a nucleophile in the aldol
condensation of ethanal?
(c) both
(d) none (i) OH– (ii) H2O
13. Which of the following is expected to be least acidic ? (iii) –CH2CHO
(a) only (i) (b) (i) and (ii)
COOH Cl COOH (c) (i) and (iii) (d) All the three
Cl
(i) O3/ H2O
(a) (b) 15. A ; A is
(i) heat

(a) CH2(COOH)2 (b) CH3COOH

(c) HCOOH (d) HCHO

ANSWER KEYS
Exercise 1 : Topic-wise MCQs
1 (b) 13 (d) 25 (b) 37 (c) 49 (c) 61 (c) 73 (d) 85 (d) 97 (a) 109 (b)
2 (c) 14 (b) 26 (d) 38 (c) 50 (c) 62 (d) 74 (b) 86 (b) 98 (c) 110 (a)
3 (c) 15 (a) 27 (b) 39 (c) 51 (d) 63 (b) 75 (b) 87 (c) 99 (c) 111 (b)
4 (a) 16 (b) 28 (b) 40 (a) 52 (c) 64 (c) 76 (b) 88 (b) 100 (b) 112 (a)
5 (b) 17 (b) 29 (d) 41 (a) 53 (d) 65 (d) 77 (a) 89 (c) 101 (c) 113 (a)
6 (a) 18 (a) 30 (b) 42 (a) 54 (a) 66 (c) 78 (c) 90 (a) 102 (a) 114 (c)
7 (d) 19 (d) 31 (d) 43 (a) 55 (b) 67 (b) 79 (c) 91 (c) 103 (d) 115 (d)
8 (a) 20 (c) 32 (b) 44 (a) 56 (a) 68 (d) 80 (d) 92 (b) 104 (d)
9 (c) 21 (a) 33 (a) 45 (d) 57 (b) 69 (c) 81 (b) 93 (d) 105 (a)
10 (b) 22 (d) 34 (c) 46 (d) 58 (b) 70 (c) 82 (a) 94 (b) 106 (b)
11 (b) 23 (d) 35 (b) 47 (a) 59 (a) 71 (d) 83 (c) 95 (c) 107 (c)
12 (b) 24 (d) 36 (d) 48 (a) 60 (b) 72 (c) 84 (d) 96 (d) 108 (b)
Exercise 2 : Exemplar & Past Year MCQs
1 (b) 6 (d) 11 (b) 16 (a) 21 (d) 26 (d) 31 (a) 36 (b) 41 (a)
2 (a) 7 (b) 12 (a) 17 (c) 22 (d) 27 (d) 32 (b) 37 (a) 42 (a)
3 (c) 8 (d) 13 (d) 18 (a) 23 (b) 28 (d) 33 (b) 38 (b) 43 (c)
4 (b) 9 (b) 14 (a) 19 (d) 24 (a) 29 (a) 34 (a) 39 (c)
5 (c) 10 (c) 15 (b) 20 (b) 25 (c) 30 (d) 35 (a) 40 (b)
Exercise 3 : Try If You Can
1 (c) 3 (d) 5 (d) 7 (c) 9 (b) 11 (b) 13 (d) 15 (b)
2 (d) 4 (d) 6 (b) 8 (c) 10 (c) 12 (c) 14 (c)