CLS Aipmt-18-19 XII Che Study-Package-7 SET-2 Chapter-12 PDF

Chapter 12
Aldehydes, Ketones and Carboxylic Acids
Solutions
SECTION - A
Objective Type Questions
(Nomenclature and Methods of Preparation of Aldehydes and Ketones)

1. The general formula of both aldehyde and ketone is
(1) CnH2n+2O (2) CnH2nO (3) CnH2n–2O (4) CnH2n+4O
Sol. Answer (2)
The general formula of aldehyde and ketone is CnH2nO.
2. The IUPAC name of following structure is
CH3
|
CH3 — CH — C— CH2 — CH2OH
||
O
(1) 1-Hydroxy-4-methylpentan-3-one (2) 2-Methyl-5-hydroxy-3-pentanone
(3) 4-Methyl-3-oxo-1-pentanol (4) Hexanol-1-one-3
Sol. Answer (1)
3
5 4 2 OH
1-hydroxy-4-methylpentan-3-one
3. IUPAC name of CCl3CHO is

(1) Chloral (2) Trichloro acetaldehyde
(3) 1,1,1-trichloroethanal (4) 2,2,2-trichloroethanal
Sol. Answer (4)
CCl3 – CHO
2, 2, 2 – trichloroethanal
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184 Aldehydes, Ketones and Carboxylic Acids Solutions of Assignment (Set-2)
4. Which of the following is mixed ketone?

(1) Pentanone (2) Acetophenone (3) Benzophenone (4) Propanone
Sol. Answer (2)
O
C CH3
This is mixed ketone.

O
||
H2
5. In the following reaction product P is R — C— Cl 
PdBaSO
P
4
(1) RCH2OH (2) RCOOH (3) RCHO (4) RCH3

Sol. Answer (3)
O
||
H2
R — C— Cl 
PdBaSO
 R  CHO
4
6. Dry heating of calcium acetate gives

(1) Acetaldehyde (2) Ethane (3) Acetic acid (4) Acetone
Sol. Answer (4)

Ca(CH3COO)2 Dry
CH3 CH3
R
7. CH3 — CH2 — C  CH 
 Butanone, R is
H3O
(1) Hg+2 (2) KMnO4 (3) KClO3 (4) K2Cr2O7

Sol. Answer (1)
O
R
C CH H
+
2+
R Hg
8. Which of the following pathways produces 2-hexanone?

(i) 1-Hexyne is treated with Hg2/dil. H2SO4.
(ii) 3-Methylhept-2-ene is treated with O3 followed by hydrolysis.
(iii) n-butyl magnesium bromide reacts with acetaldehyde followed by hydrolysis and then oxidation with
chromic acid.
(iv) Hydroboration-oxidation of 1-hexyne.
(1) (i), (ii) and (iii) (2) (i) and (ii) only (3) (i), (ii) and (iv) (4) (i) and (iii) only
Sol. Answer (1)
O
+2
Hg /dil
1 Hexyne
H2SO4
9. An alkene of molecular formula C9H18 on ozonolysis gives 2,2-dimethylpropanal and butan-2-one, then the
alkene is
(1) 2,2,4-trimethylhex-3-ene (2) 2,2,6-trimethylhex-3-ene
(3) 2,3,4-trimethylhex-2-ene (4) 2,2,4-trimethylhex-2-ene
Solutions of Assignment (Set-2) Aldehydes, Ketones and Carboxylic Acids 185
Sol. Answer (1)
(1) O3
+
(2) Zn
CHO
(i) O
10. X  3
(ii) Zn H O
 O. 'X' can be
2
CH3
(1) (2) (3) (4)
Sol. Answer (1)

O3
2 O
11. Select the reagent for the following reaction.
OHC — (CH2)4 — CHO
(1) SeO2 (2) O3, Zn/H2O

(3) O3, H2O2—CH3COOH (4) PCC
Sol. Answer (2)
X
CHO—(CH2)4—CHO
X Must be O3, Zn/H2O

(Physical and Chemical Properties of Aldehydes and Ketones)
12. Acetyl chloride is reduced with LiAlH4, the product formed is

(1) Methyl alcohol (2) Ethyl alcohol (3) Acetaldehyde (4) Acetone
Sol. Answer (2)
O
+ LiAlH4
Cl OH
13. Which factors will increase the reactivity of C O group?

(i) Presence of a group with positive inductive effect
(ii) Presence of a group with (–ve) inductive effect
(iii) Presence of large alkyl group
(1) Only (i) (2) Only (ii) (3) Both (i) & (iii) (4) Both (ii) & (iii)
Sol. Answer (2)
O If Z is (–I) effect group, then reactivity will increases because such gp increases more partial the
Z
charge density on carboxyl carbon. Which inhances nucleophilic substitution (SN) reaction and nucleophilic
addition reaction.
14. Correct order of reactivity of CH3CHO, C2H5COCH3 and CH3COCH3 with HCN
(1) CH3CHO > CH3COCH3 > CH3COC2H5 (2) C2H5COCH3 > CH3COCH3 > CH3CHO
(3) CH3COCH3 > CH3CHO > C2H5COCH3 (4) CH3COCH3 > C2H5COCH3 > CH3CHO
Sol. Answer (1)

Nucleophilic addition on carbonyl compound follows as
E – Nu  E+ + Nu–
Nu
Since, the first step is attack of Nu on carbonyl carbon, so more is the positive charge on carboxyl ‘C’ more
the probability of attack on it. Because of this, the reactivity order follows as
> >
15. The increasing order of the rate of HCN addition to compounds A–D is
(A) HCHO (B) CH3COCH3 (C) PhCOCH3 (D) PhCOPh
(1) A < B < C < D (2) D < B < C < A (3) D < C < B < A (4) C < D < B < A
Sol. Answer (3)
O O
O
H CHO > > C CH3 > C
CH 3 CH3
Because more is the positive charge on carboxyl carbon more is the reactivity.
16. The correct order of reactivity of PhMgBr towards given compounds
O O O
|| || ||
Ph — C— Ph CH3 — C— H CH3 — C— CH3
(i) (ii) (iii)
(1) (i) > (ii) > (iii) (2) (iii) > (ii) > (i) (3) (ii) > (iii) > (i) (4) (i) > (iii) > (ii)
Sol. Answer (3)
O
O
CH3 CHO > > C
Because more is the positive charge on carboxyl carbon more is the reactivity.
17. Predict the product

O
(i) CH3MgBr
+
(ii) H3O
O OH O
CH3 OH
CH3
(1) (2) (3) (4)
CH3 CH3
Sol. Answer (2)
O O
(i). CH3MgBr
+
(ii). H3O
CH3
CH3MgBr tautomerism
OMgBr O H
+
(ii). H3O
CH3 CH3
R
R
18. Reaction CO + HCN R—C—OH is
R
CN
(1) Electrophilic substitution (2) Nucleophilic addition
(3) Nucleophilic substitution (4) Electrophilic addition
Sol. Answer (2)
R
R + –
O + H CN R—C—OH
R
CN
This is nucleophilic addition.
19. Reaction of aldehyde with HCN followed by hydrolysis gives a compound which shows
(1) Optical isomerism (2) Geometrical isomerism
(3) Metamerism (4) Tautomerism
Sol. Answer (1)
H H H
+
H3O
R C O R C OH R C OH
–
CN CN COOH
(Optically active)
Due to presence of chiral center.
NaCN H O
20. (CH3 )2 CO 
(HCl)
 A 
3

B.
In the above sequence of reactions A and B are

(1) (CH3)2C(OH)CN, (CH3)2C(OH)COOH (2) (CH3)2C(OH)CNH2, (CH3)2C(OH)2
(3) (CH3)2C(OH)CN, (CH3)2CHCOOH (4) (CH3)2C(OH)CNH2, (CH3)2C == O
Sol. Answer (1)
OH +
OH
O + NaCN H
CN COOH
A B
21. Aldol condensation will not be observed in

(1) Chloral (2) Phenyl acetaldehyde
(3) Hexanal (4) Ethanal
Sol. Answer (1)
Chloral (CCl3–CHO) will not give Aldol reaction.
22. Which of the following gives aldol condensation reaction?
O
||
(1) C6H5OH (2) C6H5 C— C6H5
(3) CH3 CH2 — C— CH3 (4) (CH3 )3 C — C— C(CH3 )3

|| ||
O O
Sol. Answer (3)
CH3 CH2 C CH3 have  hydrogen. So it will given aldol reaction.
23. The diketone
O O
|| ||
CH3 — C— (CH2 )2 — C— CH3
on intramolecular aldol condensation gives the final product
O O O O
OH
(1) (2) (3) (4)
CH3 CH3 CH3
Sol. Answer (3)
O
O O
OH
H3C C CH2 CH2 C CH3 
More H3C
acidic ‘H’ OH
O O
1 2 3 4 5
H2C C CH2 CH2 C
CH3
+ H2O
O O
H 2
3
1 –H2O
4
5 CH3
HO
CH3
24. What will be the product, when carboxy phenol, obtained by Reimer-Tiemann's process, is deoxidised with Zn
powder?
OH CHO
CHO
(1) (2)
OH COOH
(3) (4)
Sol. Answer (4)
OH COOH
COOH
Zn
Dust
25. Benzyl alcohol and sodium benzoate is obtained by the action of concentrated sodium hydroxide on
benzaldehyde. This reaction is known as
(1) Perkin reaction (2) Cannizzaro reaction
(3) Sandmeyer reaction (4) Claisen condensation
Sol. Answer (2)
– –
CHO + OH COO +
OH
This is Cannizzaro reaction.
26. When m-chlorobenzaldehyde is treated with 50% Ba(OH)2 solution, the product(s) obtained is(are)
OH OH
–
COO CH2OH
CH—CH
(1) (2) +
OH OH OH
OH OH
–
COO CH2OH
CH—CH
(3) + (4)
Cl Cl Cl Cl
Sol. Answer (3)
–
CHO –
COO
OH OH
+
(50%)
Cl Cl Cl
It is an example of intermolecular Cannizzaro reaction.
CHO (i) conc. NaOH

27. + ?
(ii) H2O/H
CHO
COOH COOH COOH CH2OH

(1) (2) (3) (4)
COOH CH2OH OH CHO
Sol. Answer (2)
–
CHO –
COO
OH
OH
CHO
+
H
COOH
OH
28. Which of the following compound will exhibits positive Fehling test as well as iodoform test?
(1) Methanal (2) Ethanol (3) Propanone (4) Ethanal
Sol. Answer (4)
H3C O
29. Dimethyl ketones are usually characterised through

(1) Tollens reagent (2) Iodoform test (3) Schiff's test (4) Benedict's reagent
Sol. Answer (2)
–
+ I2 / OH
30. Trichloroacetaldehyde, CCl3CHO reacts with chlorobenzene in presence of sulphuric acid and produces
Cl
Cl
(1) Cl C Cl (2) Cl C Cl
CH2Cl H
OH
(3) Cl C Cl (4) Cl CH Cl
Cl CCl3
Sol. Answer (4)
H
+
H
CCl3 CHO + Cl Cl C Cl
CCl3
(DDT)
31. An aromatic compound 'X' with molecular formula C9H10O gives the following chemical tests
(i) Forms 2,4-DNP derivative
(ii) Reduce Tollens reagent
(iii) Undergoes Cannizzaro reaction and
(iv) On vigorous oxidation, 1,2-benzenedicarboxylic acid is obtained
The compound
CHO O CHO
C2H5 CHO C
(1) (2) (3) CH3 (4)
CH3 C2H5
C2H5
Sol. Answer (1)
CHO
+ 2, 4 DNP Test
+ Tollen's Test
+ Cannizzaro reaction
O
OH(–)
32. CHO + 'X' CH CH C . Identify 'X'
293K
O
(1) CH2—CHO (2) CH2–CH2–OH (3) C CH3 (4) CH CH2
Sol. Answer (3)
O
CHO + C CH3
–
OH
O
CH CH C
(Nomenclature and Methods of Preparation of Carboxylic Group)
33. The IUPAC name of phthalic acid

(1) Benzene-1,2-dicarboxylic acid (2) Benzene-1,4-dioic acid
(3) Cyclo-1,3,5-trien-1,2-dioic acid (4) Benzene-1,3-dicarboxylic acid
Sol. Answer (1)
COOH
Benzene –1, 2-dicarboxylic acid.
COOH
34. Saponification of ethyl benzoate with caustic soda as alkali gives

(1) Benzyl alcohol and ethanoic acid (2) Sodium benzoate and ethanol
(3) Benzoic acid and sodium ethoxide (4) Phenol and ethanoic acid
Sol. Answer (2)
C O KOH COO + OH
–
CH3
CH3 CH2
35. The major product obtained on reaction of phenol with sodium hydroxide and carbon dioxide is
(1) Benzoic acid (2) Salicylaldehyde (3) Salicylic acid (4) Phthalic acid
Sol. Answer (3)
–
OH + CO 2 + OH OH
COOH
36. Acetic acid is obtained when

(1) Methyl alcohol is oxidised with potassium permanganate
(2) Calcium acetate is distilled in the presence of calcium formate
(3) Acetaldehyde is oxidised with potassium dichromate and sulphuric acid
(4) Glycerol is heated with sulphuric acid
Sol. Answer (3)
K Cr O , H
CH3CHO 
2 2 7
CH3COOH
(Physical and Chemical Properties of Carboxylic Acids)
37. Which of the following is optically active?

(1) Ethylene glycol (2) Oxalic acid (3) Glycerol (4) Tartaric acid
Sol. Answer (4)
Tartaric acid has chiral centre.
38. Which of the following does not give benzoic acid on hydrolysis?
(1) Phenyl cyanide (2) Benzoyl chloride (3) Benzyl chloride (4) Methyl benzoate
Sol. Answer (3)
+ H2O
Cl OH
39. A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a fruity smell
was formed. The liquid was
(1) CH3OH (2) HCHO (3) CH3COCH3 (4) CH3COOH
Sol. Answer (4)
+
H
+ Ester
CH3 OH
CH 3 OH
40. Which of the following aromatic acids is most acidic?
COOH COOH COOH COOH

OH
(1) (2) (3) (4)
OH
OH
Sol. Answer (2)
COOH
OH
This is most acidic because of ortho effect.

41. CH3 COOH 
PO
 X . Identify X
2 5
(1) CH3COCH3 (2) CH3CHO (3) (CH3CO)2O (4) CH4

Sol. Answer (3)

+
OH HO P2O5
42. Which one of the following orders of acid strength is correct?

(1) RCOOH > HC  CH > HOH > ROH (2) RCOOH > ROH > HOH > HC  CH
(3) RCOOH > HOH > ROH > HC  CH (4) RCOOH > HOH > HC  CH > ROH
Sol. Answer (3)
Stability order of CB’s R  CO2  OH  R  O  C  CH
 Acidic strength order R  CO2H  H2O  R  OH  HC  CH
43. Which of the following presents the correct order of the acidity in the given compounds?
(1) CH3COOH > BrCH2COOH > ClCH2COOH > FCH3COOH
(2) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH
(3) BrCH2COOH > ClCH2COOH > FCH2COOH > CH3COOH
(4) FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
Sol. Answer (4)
FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
44. The correct order of acidic strength of the carboxylic acid is

(1) Formic acid < Benzoic acid < Acetic acid (2) Formic acid < Acetic acid < Benzoic acid
(3) Acetic acid < Formic acid < Benzoic acid (4) Acetic acid < Benzoic acid < Formic acid
Sol. Answer (4)
Acidic strength order
> >
> >
Because the S.O of CB' is
As, the acidic strength order 1 > 2 > 4 > 3.
So, BrCH2CH2CO2H is weakest acid and hence it has smallest value of dissociation constant.
45. Which of the following acids has the smallest value of dissociation constant?
(1) CH3CHFCOOH (2) FCH2CH2COOH
(3) BrCH2CH2COOH (4) CH3CHBrCOOH
Sol. Answer (3)
As, the acidic strength order 1 > 2 > 4 > 3. So, BrCH2CH2CO2H is weakest acid and hence it has smallest
value of dissociation constant.

 
BrCH2CH2COO  H
BrCH2CH2COOH
46. Treatment of benzoic acid with Cl2/FeCl3 will give

(1) p-chlorobenzoic acid (2) o-chlorobenzoic acid
(3) 2-4-dichlorobenzoic acid (4) m-chlorobenzoic acid
Sol. Answer (4)
COOH COOH
Cl2/FeCl3
Cl
(m - chlorobenzoic acid)
47. In esterification
(1) OH– of acid is replaced by C6H5OH (2) H+ of acid is replaced by sodium metal
(3) OH– of alcohol is replaced by chlorine (4) OH– of acid is replaced by RO– group
Sol. Answer (4)
R – O H + HO – C – R
R O C R
48. The reaction,
P
CH3COOH + Cl2   ClCH2COOH + HCl
is called
(1) Hell-Volhard-Zelinsky reaction (2) Birch reaction
(3) Rosenmund reaction (4) Hunsdiecker reaction
Sol. Answer (1)
P
CH3 C OH + Cl2 Cl CH2 COOH
+
HCl
This is H–V–Z reaction.
COOH
NH3
49.  A. Identify 'A'
COOH
(1) Benzene (2) Phthalimide (3) Benzamide (4) Acetaldehyde
Sol. Answer (2)
O O
OH NH3
N H Phthalimide
OH 
O O
50. Identify the wrong statement from the following.

(1) Salicylic acid is a monobasic acid
(2) Methyl salicylate is an ester
(3) Salicylic acid gives violet colour with neutral ferric chloride as well as brisk effervescence with sodium
bicarbonate
(4) Methyl salicylate does not occur in natural oils
Sol. Answer (4)
Methyl salicylate does not occur in natural oils.
SECTION - B
Objective Type Questions
(Nomenclature and Methods of Preparation of Aldehydes and Ketones)
MgBr
dry
ether H2O
1. HCN + A B , B is
(1) Cyclopropanol (2) Cyclopropanal
(3) Cyclopropanecarbaldehyde (4) Cyclopropanenitrile
Sol. Answer (3)
MgBr
dry
HCN +
This is wrong question because acid base reaction will dominate over nucleophilic addition reaction.
O3/Zn
2. H2O Product. The product is
(1) O = CH—CH2—C—(CH2)4—CHO (2)

|| CHO
O O O
O
O
(3) (4)
CHO O
CHO CHO CHO
Sol. Answer (3)
H
O3 / Zn
3. Clemmensen reduction of a ketone is carried out in the presence of which of the following?
(1) H2 and Pt as catalyst (2) Glycol with KOH (3) Zn-Hg with HCl` (4) LiAlH4
Sol. Answer (3)
Zn-Hg with HCl. (Clemmensen reduction)
4. In the following sequence of reactions

KCN H O LiAlH
CH3  Br   A 
3
 B  4
ether
 C,
the end product (C) is

(1) Acetaldehyde (2) Ethyl alcohol (3) Acetone (4) Methane
Sol. Answer (2)
H LiAlH
CH3  Br  CN  CH3CN 
 CH3COOH 
4
 CH3CH2OH
(Physical and Chemical Properties of Aldehydes and Ketones)
SeO2 HIO4 CaO

5.

A 
B 
C
H2SO5

D
C and D are respectively
(1) Adipic acid, -lectone
(2) Cyclobutane, -lectone
(3) Cyclobutanone, -lectone
(4) Adipic acid, -lectone
Sol. Answer (3)
O O
O
(1) SeO2
(2) HIO4  O O
H2SO5 O
O

O C OH
(3) CaO
+ CaCO3

C OH
Cyclobutanone
O
6. In the reaction
CHO
Conc. KOH
+ HCHO Product
If one equivalent of each is taken, the major product will be

O O
C CH2 OH C CHO CH2OH
(1) + HCOOH (2) +
OH COOH
CH2 CH CHO
(3) + HCOOH (4)
Sol. Answer (3)

–
CHO COO CH2OH
–
OH –
+ HCHO HCOO + +
+ CH3OH
The products shown in boxes are major product.
In cross-cannizzaro reaction, the carbonyl carbon having more positive charge is oxidised to acid and the other
carbonyl is reduced to alcohol.
LiAlH4
CH = CH – CHO Product
7. .
Product of the reaction is
(1) CH2 – CH2 – CHO (2) CH2 – CH2 – CHO
CH2 – CH2CH2 OH CH = CH – CH2OH

(3) (4)
Sol. Answer (4)

CHO CH2OH
LiAlH4
8. The number of total final products formed in given reaction

–
OH
CH 3 CHO 
(1) 1 (2) 2 (3) 3 (4) 4
Sol. Answer (2)
O
–
OH
CH3 CHO  H C CH CH CH3
E&Z
9. Iodoform reaction is given by
O O
(1) CH = CH – C – CH3 (2) C
(3) CH3 – CH2 – CHO (4) All of these

Sol. Answer (1)
C
CH3
_
I2/OH
–
O
CHI3 +
10. Aromatic aldehydes undergoes condensation on heating with an ethanolic solution of KCN. This reaction is
called as
(1) Perkin reaction (2) Benzoin condensation
(3) Claisen condensation (4) Cannizzaro’s reaction
Sol. Answer (2)
O OH
–
CHO + CN C CH
This is benzoin reaction.
11. Which of the following carbonyl compound can give Cannizzaro reaction?
(1) CCl3CHO (2) (CH3)3CCHO (3) CH3CH2CHO (4) Both (1) & (2)
Sol. Answer (2)
–
CHO OH Cannizzaro reaction
12. The reactivity of carbonyl compounds towards nucleophilic addition reaction gets affected by
(1) Magnitude of positive charge on carbonyl carbon atom
(2) Steric hindrance
(3) Presence of electron withdrawing groups surrounding carbonyl group
(4) All of these
Sol. Answer (4)
R electrophilicity
O
R Steni Hindirance
13. Which of the following statement is incorrect about the reaction of ammonia derivatives with carbonyl compounds?
(1) pH of solution is maintained between 3 to 4
(2) Addition of ammonia derivatives occurs followed by elimination of H2O
(3) At very low pH (less than 3) ammonia derivatives are protonated and do not act as nucleophile
(4) At very high pH reaction becomes explosive
Sol. Answer (4)
At very high temperature and at high pH reaction becomes explosive.
14. An organic compound does not reacts with Tollen’s reagent but undergoes Baeyer Villiger oxidation. The compound
is CHO
O
(1) CH  C–CH2COCH3 (2) (3) CH3CHO (4) CH 3 – C – CH 3
O
Sol. Answer (4)
No Tollen's test
+ B.V. Oxidation
15. Following compounds are given
a. CH3CH2OH b. CH3COCH3 c. CH 3 CHOH d. CH3OH
CH 3
Which of the above compound(s), on being warmed with iodine solution and NaOH, will give iodoform?
(1) a, c & d (2) Only b (3) a, b & c (4) a & b
Sol. Answer (3)
–
I2, OH
CH3CH2OH CHI3
–
I2, OH
CHI3
–
I2, OH
CH3 CH OH CHI3
CH3
16. A strong base can abstract an -hydrogen from

(1) Alkane (2) Alkene (3) Ether (4) Ketone
Sol. Answer (4)
O O
CH3 C CH2 CH3 C CH2
H – –
OH O
CH3 C CH3
17. Iodoform test is not given by

(1) Ethanal (2) Ethanol
(3) 2-pentanone (4) 3-pentanone
Sol. Answer (4)
–
+ I2, OH No reaction
18. Which of the following reactions will not result in the formation of carbon-carbon bonds?
(1) Friedel-Craft’s acylation
(2) Reimer-Tiemann reaction
(3) Cannizzaro reaction
(4) Wurtz reaction
Sol. Answer (3)
Cannizzaro reaction do not involve C—C bond formation.
(Nomenclature and Methods of Preparation of Carboxylic Group)
SOCl2 benzene HCN

19. In a set of reactions acetic acid yielded a product D. CH 3 COOH   A   B 
anhy. AlCl3
The structure of D would be HOH
C  D
COOH CN
C – CH3 C–CH3
(1) (2)
OH OH
OH OH
CH2–C–CH3 (CH2)2–C–CH3
(3) (4)
CN CN
Sol. Answer (1)

O OH
O O +
HCN, H3O
+ HOCl2 C CH3 CH3
OH (A) Cl AlCl3 (B)
(D) COOH
20. An organic compound 'A' on treatment with NH3 gives 'B' which on heating gives 'C' when treated with Br2 in
presence of KOH produces ethylamine. Compound 'A' is
(1) CH3 — CHCOOH (2) CH3CH2COOH (3) CH3COOH (4) CH3CH2CH2COOH
CH3
Sol. Answer (2)

OH NH2 –
Br2OH
+ NH3 NH2
O O
21. Which of the following compound gives benzoic acid on hydrolysis?

(1) Chlorobenzene (2) Benzoyl chloride (3) Chlorophenol (4) Chlorotoluene
Sol. Answer (2)
O O
C Cl + H2O C OH
22. In a set of reactions, ethyl benzene yielded a product D.
KMnO4 Br2 C2H5OH
CH2CH3 KOH B FeCl3 C H
+ D
‘D’ would be
COOC2H5
CH2–CH–COOC2H5
(1) (2)
Br Br
Br COOH
(3) (4)
Br OCH2CH3
CH2COOC2H5
Sol. Answer (1)

O O
COOH COOH C Et C O Et
KMnO4 Br2 OH
+3 +
Fe H
Br Br Br
(B) (C) (D)
23. What is Z in following sequence of reactions?
Zn CH Cl
alkaline
Phenol 
 X  
3
 Y   Z
dust anhydrous AlCl3 KMnO 4
(1) Benzene (2) Toluene (3) Benzaldehyde (4) Benzoic acid
Sol. Answer (4)

O
Zn (i) CH3Cl, AlCl3
OH – C
(ii) KMnO4, OH
OH
24. Which of the following is the correct sequence of decreasing reactivity towards hydroxide ion promoted hydrolysis
among the following compounds?
O H O H O H O H
NO2 || | || |
|| | || |
CH3–C–N CH3–C–N CH3–C–N NO2 CH3–C–N
(I) (II) (III) (IV)
(1) I > II > III > IV (2) II > I > IV > III (3) III > II > IV > I (4) I > III > II > IV
Sol. Answer (3)
The correct order is (3). It will depend on stability of anion.
+
P2 O 5 H /H2 O
25. CH3CH2COONH4 X Y.

Y and X respectively are
(1) CH3CH2COOH, CH3CH2CN (2) CH3CH2CN, CH2CH2COOH
(3) CH3CH2CH2COOH, CH3CH2CH3 (4) CH3CH3, CH3CH2COOCH3
Sol. Answer (1)
+
P2O5 H
CH3CH2COONH4 CN COOH

(X) (Y)
(Physical and Chemical Properties of Carboxylic Acids)
26. Acetic acid exist in dimer state in benzene due to

(1) Condensation reaction (2) Hydrogen bonding
(3) Presence of carbonyl group (4) Strong polar nature
Sol. Answer (2)
CH3
O H O
O CH3
H O
Hydrogen bonding
27. When HCOOH acid is heated with conc. H2SO4, the gas evolved is
(1) Only CO2 (2) CO + CO2 (3) SO2 + CO2 (4) CO
Sol. Answer (4)
HCOOH  H2SO4 
 CO 
28. The correct order of decreasing acid strength of trichloroacetic acid (A), trifluoroacetic acid (B), acetic acid (C) and
formic acid (D) is
(1) A > B > C > D (2) A > C > B > D (3) B > A > D > C (4) B > D > C > A
Sol. Answer (3)
F Cl
F C COOH > Cl C COOH > HCOOH > CH3COOH
F Cl
29. Which one of the following products is formed when adipic acid is heated?
CH2CH2CO CH2CH2COOH CH2 CH2 CH2—CH2

(1) O (2) (3) O (4) C=O
CH2CH2CO CH2CH2COOH CH2 CH2 CH2—CH2
Sol. Answer (4)
Adipic acid O
30. Aspirin is an acetylation product of
(1) m-Hydroxybenzoic acid
(2) o-Dihydroxybenzene
(3) o-Hydroxybenzoic acid
(4) p-Dihydroxybenzene
Sol. Answer (3)
O
OH O C CH3
O
COOH COOH
+ CH3 C Cl
31. Which one of the following compounds will react with NaHCO3 solution to give sodium salt and carbon dioxide?
(1) Acetic acid
(2) n-hexanol
(3) Phenol
(4) Both (2) & (3)
Sol. Answer (1)
O
O
– +
+ NaHCO 3 CH3 C O Na + CO 2+ H2O
CH 3 OH
32. Ethyl benzoate can be prepared from benzoic acid by using

(1) Ethyl alcohol (2) Ethyl alcohol and dry HCl
(3) Ethyl chloride (4) Sodium ethoxide
Sol. Answer (2)
C Et COOH
+
H +
OH
33. In a set of the given reactions, acetic acid yielded a product C

C6H6 C2H5MgBr
CH3COOH + PCl5  A B ether
C
Anh. AlCl3
Product C would be C2H5
(1) CH3CH(OH)C2H5 (2) CH3COC6H5 (3) CH3CH(OH)C6H5 (4) CH3–C(OH)C6H5
Sol. Answer (4)
O Et
O O
, AlCl3 MgBr, ether
+ PCl5 C CH3 CH3 C C6H5
OH Cl
OH
34. The OH group of an alcohol or carboxylic acid can be replaced by –Cl using
(1) Phosphorus pentachloride (2) Hypochlorous acid
(3) Chlorine (4) Hydrochloric acid
Sol. Answer (1)
O O
R C OH + PCl5 R C Cl
35. Propionic acid with Br2 / P yields a dibromo product. Its structure would be
Br
(1) CH3 C COOH (2) CH2Br—CHBr—COOH
Br
Br
(3) H C CH2COOH (4) CH2Br—CH2—COBr
Br
Sol. Answer (1)
Br
CH3 C COOH
Br
Br / P excess of NH
36. CH3 CH2COOH 2
 A    
3
 Y.
The product Y is
(1) Lactic acid (2) n-propyl amine (3) Ethylamine (4) Alanine
Sol. Answer (4)
Br
Br2/P
H3C CH2 CO2H H3C CH CO2H
(A)
NH3
(xs)
NH2
H3C CH CO2H
Alanine
O
16 18 dil. H2SO4
37. CH3 – C – O – H + R – O – H 
Major product.
Product of the reaction is
O O O
18 16 18
(1) CH3 – C – O – R (2) CH3 – C – O – R (3) R – C – O – CH3 (4) R – C – O – R
16
Sol. Answer (1) O
O
16 + R
1
O 18
OH
+
H , H
O
18 1
CH3 C O R
38. The product D of the reaction
KCN H2O/H+ NH3 
CH3Cl A B C D is
(1) HCONH2 (2) CH3CN (3) CH3CH2NH2 (4) CH3CONH2
Sol. Answer (4)
+
– H NH3
CH3Cl + CN CH3CN CH3COOH CH3CONH2
H2O
(D)
39. The relative reactivities of acyl compounds towards nucleophilic substitution are in the order of
(1) Acyl chloride > Ester > Acid anhydride > Amide
(2) Acyl chloride > Acid anhydride > Ester > Amide
(3) Ester > Acyl chloride > Amide > Acid anhydride
(4) Acid anhydride > Amide > Ester > Acyl chloride
Sol. Answer (2)
O O O O O
R C Cl > CH3 C O C CH 3 > R C OR > R C NH2 Order of reactivity
SECTION - C
Previous Years Questions

1. Carboxylic acids have higher boiling points than aldehydes, ketones and even alcohols of comparable molecular
mass. It is due to their [NEET-2018]
(1) Formation of intramolecular H-bonding
(2) Formation of carboxylate ion
(3) Formation of intermolecular H-bonding
(4) More extensive association of carboxylic acid via van der Waals force of attraction
Sol. Answer (3)
Due to formation of intermolecular H-bonding in carboxylic acid, association occurs. Hence boiling point
increases and become more than the boiling point of aldehydes, ketones and alcohols of comparable molecular
masses.
2. Compound A, C8H10O, is found to react with NaOI (produced by reacting Y with NaOH) and yields a yellow
precipitate with characteristic smell. [NEET-2018]
A and Y are respectively
(1) H3C CH2 – OH and I2
(2) CH2 – CH2 – OH and I2
CH3
(3) CH3 OH and I2
(4) CH – CH3 and I2

OH
Sol. Answer (4)

Option (4) is secondary alcohol which on oxidation gives phenylmethyl ketone (Acetophenone). This on reaction
with I2 and NaOH form iodoform and sodium benzoate.
2NaOH  I2  NaOI  NaI  H2O

NaOI
CH – CH3 C – CH3
OH O
Acetophenone
(A)
I2
COONa + CHI3 NaOH
Iodoform
Sodium benzoate (Yellow PPt)
3. Of the following, which is the product formed when cyclohexanone undergoes aldol condensation followed by
heating? [NEET-2017]
(1) (2) (3) (4)
OH O OH O O
Sol. Answer (2)
O O
H
(i) OH(–)
+ H
(ii) 
4. Consider the reactions :

+
Cu / [Ag(NH3)2]
X A Silver mirror observed
573 K –OH, 
(C2H6O)
–OH, 
Y
O
NH2 – NH – C – NH2
Z
Identify A, X, Y and Z [NEET-2017]
(1) A-Methoxymethane, X-Ethanoic acid, Y-Acetate ion, Z-hydrazine
(2) A-Methoxymethane, X-Ethanol, Y-Ethanoic acid, Z-Semicarbazide
(3) A-Ethanal, X-Ethanol, Y-But-2-enal, Z-Semicarbazone
(4) A-Ethanol, X-Acetaldehyde, Y-Butanone, Z-Hydrazone
Sol. Answer (3)
Since 'A' gives positive silver mirror test therefore, it must be an aldehyde or -Hydroxyketone.
Reaction with semicarbazide indicates that A can be an aldehyde or ketone.
Reaction with OH– i.e., aldol condensation (by assuming alkali to be dilute) indicates that A is aldehyde as
aldol reaction of ketones is reversible and carried out in special apparatus.
These indicates option (3).
+ –
Cu [Ag(NH3)2] ,OH
CH3–CH2OH CH3–CHO CH3–COOH
573 K 
(X) (A)
ethanal
O
OH
–
H2N – NH – C – NH2 OH
CH3 – CH – CH2 – CHO
O
3-Hydroxybutanal
CH3 – CH = N – NH – C – NH2 
(Z)
CH3 – CH = CH – CHO
(Y)
But-2-enal
5. The correct structure of the product A formed in the reaction
O
H2(gas, 1 atmosphere)
A
Pd/carbon, ethanol
is [NEET-(Phase-2)-2016]
OH O OH OH
(1) (2) (3) (4)
Sol. Answer (2)
O O
H2(gas, 1 atm.)
Pd/carbon, ethanol
6. The correct order of strengths of the carboxylic acids
COOH COOH COOH
O
O
I II III
is [NEET-(Phase-2)-2016]
(1) I > II > III (2) II > III > I
(3) III > II > I (4) II > I > III
Sol. Answer (2)
On the basis of –I effect, the correct acidic strength would be
COOH COOH COOH

> >
O
O
II III I
7. Reaction of a carbonyl compound with one of the following reagents involves nucleophilic addition followed by
elimination of water. The reagent is [Re-AIPMT-2015]
(1) Hydrocyanic acid (2) Sodium hydrogen sulphite
(3) A Grignard reagent (4) Hydrazine in presence of feebly acidic solution
Sol. Answer (4)
Feebly acidic
C = O + H2N – NH2 C – OH
NH
NH2
–H2O
C = N – NH2
8. Which one of the following esters gets hydrolysed most easily under alkaline conditions? [Re-AIPMT-2015]
OCOCH3 OCOCH3
(1) (2)
Cl
OCOCH3 OCOCH3
(3) (4)
O2N H3CO
Sol. Answer (3)
Since –NO2 has strong –I and –R effect, it will favour hydrolysis of ester most.
9. The oxidation of benzene by V2O5 in the presence of air produces [Re-AIPMT-2015]

(1) Benzoic acid (2) Benzaldehyde
(3) Benzoic anhydride (4) Maleic anhydride
Sol. Answer (4)
Fact.
10. Treatment of cyclopentanone O with methyl lithium gives which of the following species?
[AIPMT-2015]
(1) Cyclopentanonyl biradical (2) Cyclopentanonyl anion
(3) Cyclopentanonyl cation (4) Cyclopentanonyl radical
Sol. Answer (2)

CH3 Li —
O O
CH3
11. An organic compound "X" having molecular formula C5H10O yields phenyl hydrazone and gives negative response
to the Iodoform test and Tollen's test. It produces n-pentane on reduction. 'X' could be : [AIPMT-2015]
(1) n-amyl alcohol (2) Pentanal (3) 2-pentanone (4) 3-pentanone
Sol. Answer (4)
X
[C5H 10O] yields phenylhydrazone which confirm the presence of carbonyl gp.
O
 It gives negative response to the iodoform test and tollen's test which confirm the absence of C CH3
gp.
 Therefore, from above condition it is obvious that ‘X’ is 3-Pentanone.
O
H3C CH2 C CH2 CH3
12. Which of the following will not be soluble in sodium hydrogen carbonate? [AIPMT-2014]
(1) 2,4,6 -trinitrophenol (2) Benzoic acid
(3) o-Nitrophenol (4) Benzenesulphonic acid
Sol. Answer (3)
o-nitrophenol is weaker acid than HCO3–.
13. Which one is most reactive towads Nucleophilic addition reaction? [AIPMT-2014]
CHO CHO
CHO COCH3
(1) (2) (3) (4)
CH3 NO2
Sol. Answer (4)

The gp which increases more positive charge on carbonyl carbon, increases reactivity of nucleophilic addition.
Now, As ‘–NO2’ gp is –M and –I effecting gp therefore it increases the positive charge on carbonyl carbon and
hence reactivity of nucleophilic addition reaction.
14. Reaction by which Benzaldehyde cannot be prepared [NEET-2013]
COCl
(1) + H2 in presence of Pd-BaSO4 (2) +CO+HCl in presence of anhydrous AlCl3
COOH CH3
(3) + Zn/Hg and conc. HCl (4) +CrO2Cl2 in CS2 followed by H3O+
Sol. Answer (3)
15. The correct order of decreasing acid strength of trichloroacetic acid (A),trifluoroacetic acid (B), acetic acid (C) and
formic acid (D) is [AIPMT (Prelims)-2012]
(1) A > B > C > D (2) A > C > B > D (3) B > A > D > C (4) B > D > C > A
Sol. Answer (3)
Electron withdrawing group increases the acidic character.
CF3COOH > CCl3COOH > HCOOH > CH3COOH
16. In the following sequence of reactions
KCN H O LiAlH
CH3– Br   A 
3
B  4
ether
 C,
the end product (C) is [AIPMT (Prelims)-2012]
(1) Acetaldehyde (2) Ethyl alcohol (3) Acetone (4) Methane
Sol. Answer (2)
+
KCN H3O
CH3Br CH3CN CH3COOH
A LiAlH4
B ether
CH3CH2OH
17. Predict the products in the given reaction

CHO
50% KOH
Cl
[AIPMT (Prelims)-2012]
–
CH2OH COO
– CH2OH COO
(1) (2) +
+
Cl Cl OH OH
–
CH2OH CH2COO CH2OH OH
(3) + (4) +
Cl Cl OH OH
Sol. Answer (1)
–
CHO COO
50% OH
+
KOH
Cl Cl Cl
18. Which of the following acids does not exhibit optical isomerism? [AIPMT (Prelims)-2012]
(1) Lactic acid (2) Tartaric acid (3) Maleic acid (4) -amino acids
Sol. Answer (3)
Maleic acid.
19. CH3CHO and C6H5CH2CHO can be distinguished chemically by [AIPMT (Prelims)-2012]

(1) Tollen's reagent test (2) Fehling solution test (3) Benedict test (4) Iodoform test
Sol. Answer (4)
–
I2, OH
CH3 CHO +ve Tollen's test
–
I2, OH
CH2 CHO –ve Tollen's test
20. Acetone is treated with excess of ethanol in the presence of hydrochloric acid. The product obtained is
OH OC2H5
(1) (CH3)2C (2) (CH3)2C
OC2H5 OC2H5
O O
(3) CH 3CH2CH 2—C—CH 3 (4) CH3CH2CH2—C—CH2CH2CH3

Sol. Answer (2)
O OC2H5
HCl
CH3 — C — CH3 + C2H5OH CH3 — C — CH3
(excess)
OC2H5
21. Consider the following reaction
COCl
H2
Pb – BaSO4
A
The product A is [AIPMT (Mains)-2012]

(1) C6H6CHO (2) C6H5OH (3) C6H5COCH3 (4) C6H5Cl
Sol. Answer (1)
O O
C Cl C H
H2
Pb – BaSO4
22. Consider the reaction

RCHO + NH2NH2  RCH = N – NH2
What sort of reaction is it? [AIPMT (Mains)-2012]
(1) Electrophilic addition - elimination reaction (2) Free radical addition - elimination reaction
(3) Electrophilic substitution - elimination reaction (4) Nucleophilic addition - elimination reaction
Sol. Answer (4)
R – CHO + NH2 – NH2  R – CH = N – NH2
This is nucleophilic addition elimination reaction.
23. In a set of reactions m-Bromobenzoic acid gave a product D. Identify the product D
COOH
SOCl2 NH3 NaOH
B C Br2
D
Br
A
COOH NH2
CONH2 SO2NH2
(1) (2) (3) (4)

Br Br NH2 Br
Sol. Answer (4)

O
COOH COCl C – NH2 NH2
–
SOCl2 NH3 Br2, OH
Br Br Br Br
(B) (C) (D)
24. Which one is a nucleophilic substitution reaction among the following? [AIPMT (Prelims)-2011]
(1) CH3CHO + HCN  CH3CH(OH)CN

(2) CH3CH = CH2 + H2O H
 CH3– CH – CH3
OH
(3) RCHO + RMgX  R – CH – R
OH
CH3 CH3
(4) CH3– CH2– CH – CH2Br + NH3  CH3– CH2 – CH – CH2 NH2

Sol. Answer (4)
Fact.
25. Clemmensen reduction of a ketone is carried out in the presence of which of the following?
(1) H2 and Pt as catalyst (2) Glycol with KOH
(3) Zn-Hg with HCl (4) LiAlH4
Sol. Answer (3)
Zn-Hg
C O HCl CH 2 ; clemmensen reduction .
26. An organic compound 'A' on treatment with NH3 gives 'B' which on heating gives 'C' when treated with Br in
the presence of KOH produces ethylamine. Compound 'A' is [AIPMT (Mains)-2011]
(1) CH3 – CHCOOH (2) CH3CH2COOH (3) CH3COOH (4) CH3CH2CH2COOH

CH3
Sol. Answer (2)
O
NH3 –+
CH3 – CH2 – COOH CH3CH2C – ONH4
(A) (B)
O
CH3 – CH2 – C – NH2
(C)
KOH + Br2
CH3 – CH2 – NH2

Ethyl amine
27. Match the compounds given in Column-I with Column-II and select the suitable option using the code given below
Column-I Column-II
a. Benzaldehyde (i) Phenolphthalein
b. Phthalic anhydride (ii) Benzoin condensation
c. Phenyl benzoate (iii) Oil of wintergreen
d. Methyl salicylate (iv) Fries rearrangement [AIPMT (Mains)-2011]
(1) a(ii), b(iii), c(iv), d(i) (2) a(ii), b(i), c(iv), d(iii)
(3) a(iv), b(i), c(iii), d(ii) (4) a(iv), b(ii), c(iii), d(i)
Sol. Answer (2)
Fact.
28. The order of reactivity of Phenyl magnesium bromide (PhMgBr) with the following compounds
CH3 CH3 Ph
C = O, C = O and C=O
H H3C Ph
[AIPMT (Mains)-2011]
(1) I > III > II (2) I > II > III (3) III > II > I (4) II > I > III
Sol. Answer (2)
Electron density increases from I to III on carbonyl carbon.
29. Given are cyclohexanol(I), acetic acid(II), 2,4,6-trinitrophenol (III) and phenol(IV). In these the order of decreasing
acidic character will be [AIPMT (Prelims)-2010]
(1) III > II > IV > I (2) II > III > I > IV (3) II > III > IV > I (4) III > IV > II > I
Sol. Answer (1)
O
O2N NO2
NO2
Maximum resonance stabilized and maximum-I and –M effect due to three –NO2 groups, therefore more acidic
than CH3COOH.
30. In a set of reactions, ethyl benzene yielded a product D
CH2CH3 KMnO4 Br C H OH

KOH
 B 2
FeCl

 C 
2 5
 D
3 H
D would be [AIPMT (Prelims)-2010]

Br
CH2–CH–COOC2H5
(1) (2)
Br Br
CH2COOC2H5
COOH COOC2H5
(3) (4)
OCH2CH3 Br
Sol. Answer (4)
COOH COOC2H5
Br2 C2H5OH
COOH FeCl3 H+
Br Br
C D
B
31. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(1) CH3COOCH3 (2) CH3CONH2 (3) CH3COOCOCH3 (4) CH3COCl
Sol. Answer (4)
Cl– is a weakest base, therefore good leaving group.
32. Which of the following reactions will not result in the formation of carbon-carbon bonds ?
(1) Reimer-Tieman reaction (2) Cannizaro reaction
(3) Wurtz reaction (4) Friedel-Crafts acylation
Sol. Answer (2)
Cannizzaro reaction involves disproportionation.
33. Following compounds are given
a. CH3CH2OH b. CH3COCH3 c. CH3–CHOH d. CH3OH

CH3
Which of the above compound(s), on being warmed with iodine solution and NaOH, will give iodoform ?
[AIPMT (Mains)-2010]
(1) a, c and d (2) Only b (3) a, b and c (4) a and b
Sol. Answer (3)
O OH
Terminal CH 3 C or CH3 C show positive iodoform test.
34. Propionic acid with Br2|P yields a dibromo product. Its structure would be [AIPMT (Prelims)-2009]
Br Br
(1) H–C–CH 2COOH (2) CH2Br–CH2–COBr (3) CH3–C–COOH (4) CH2Br–CHBr–COOH
Br Br
Sol. Answer (3)
35. Trichloroacetaldehyde, (CCl3CHO) reacts with chlorobenzene in presence of sulphuric acid and produces
Cl
OH
(1) Cl C Cl (2) Cl C Cl
H Cl
Cl
(3) Cl CH Cl (4) Cl C Cl
CCl3 CH2Cl
Sol. Answer (3)
36. A strong base an abstract an -hydrogen from [AIPMT (Prelims)-2008]

(1) Alkane (2) Alkene (3) Amine (4) Ketone
Sol. Answer (4)
37. The relative reactivities of acyl compounds towards nucleophilic substitution are in the order of
(1) Acyl chloride > Ester > Acid anhydride > Amide (2) Acyl chloride > Acid anhydride > Ester > Amide
(3) Ester > Acyl chloride > Amide > Acid anhydride (4) Acid anhydride > Amide > Ester > Acyl chloride
Sol. Answer (2)
38. Acetophenone when reacted with a base, C2H5ONa, yields a stable compound which has the structure ?
CH—CH— C=CH—C–
(1) (2)
OH OH CH3 O
CH3 CH3
CH—CH2C
(3) (4) C C
CH3 O
OH OH
Sol. Answer (2)
39. Which of the following presents the correct order of the acidity in the given compounds ?
(1) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH
(2) BrCH2COOH > ClCH2COOH > FCH2COOH > CH3COOH
(3) FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
(4) CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH
Sol. Answer (3)
40. The product formed in Aldol condensation is [AIPMT (Prelims)-2007]

(1) An alpha, beta unsaturated ester (2) A beta-hydroxy acid
(3) A beta-hydroxy aldehyde or a beta-hydroxy ketone (4) An alpha-hydroxy aldehyde or ketone
Sol. Answer (3)
Aldol product is called -hydroxy aldehyde or -hydroxy ketone.
41. Reduction of aldehydes and ketones into hydrocarbons using zinc amalgam and conc. HCl is called
(1) Wolf-Kishner Reduction (2) Clemmensen Reduction
(3) Cope Reduction (4) Dow Reduction
Sol. Answer (2)
O
Zn(Hg), HCl
R – CHO & R R Clemmensen reduction
42. Consider the following compounds
(a) C6H5COCl (b) O 2N COCl (c) H 3C COCl (d) OHC COCl
The correct decreasing order of their reactivity towards hydrolysis is [AIPMT (Prelims)-2007]
(1) (b) > (d) > (a) > (c) (2) (b) > (d) > (c) > (a) (3) (a) > (b) > (c) > (d) (4) (d) > (b) > (a) > (c)
Sol. Answer (1)
43. Which of the compounds with molecular formula C5H10 yields acetone on ozonolysis ? [AIPMT (Prelims)-2007]
(1) 2 – Methyl – 1 – butene (2) 2 – Methyl – 2 – butene
(3) 3 – Methyl – 1 – butene (4) Cyclopentane
Sol. Answer (2)
44. In a set of reactions propionic acid yielded a compound D
SOCl2 NH2 KOH 

CH3CH2COOH  B  C 
Br2
D
The structure of D would be [AIPMT (Prelims)-2006]

(1) CH3CH2CH2NH2 (2) CH3CH2CONH2 (3) CH3CH2NHCH3 (4) CH3CH2NH2
Sol. Answer (4)
45. A carbonyl compound reacts with hydrogen cyanide to form cyanohydrin which on hydrolysis forms a racemic
mixture of –hydroxy acid. The carbonyl compound is [AIPMT (Prelims)-2006]
(1) Acetaldehyde (2) Acetone (3) Diethylketone (4) Formaldehyde
Sol. Answer (1)
OH
–
CH3 CHO CN CH3 CH
CN
46. Nucleophilic addition reaction will be most favoured in [AIPMT (Prelims)-2006]
O
(1) CH3 – CH2 – CH2C – CH3 (2) (CH3)2C = O
(3) CH2CH2CHO (4) CH3CHO

Sol. Answer (4)
CH3CHO is most reactive towards Nucleophilic addition reaction.
47. Self condensation of two moles of ethyl acetate in presence of sodium ethoxide yields
(1) Ethyl butyrate (2) Acetoacetic ester (3) Methyl acetoacetate (4) Ethyl propionate
Sol. Answer (2)
48. Which of the following is not chiral ? [AIPMT (Prelims)-2006]

(1) 2-Butanol (2) 2, 3-diBromopentane
(3) 3-Bromopentane (4) 2-Hydroxypropanoic acid
Sol. Answer (3)
49. Products of the following reaction

(1) O
CH3C  C.CH2CH3  3
(2) Hydrolysis
 ....... are [AIPMT (Prelims)-2005]
(1) CH3CHO + CH3CH2CHO (2) CH3COOH + CH3COCH3
(3) CH3COOH + HOOC . CH2CH3 (4) CH3COOH + CO2
Sol. Answer (3)
50. In a set of reactions, acetic acid yielded a product D
SOCL 2
CH3COOH  Benzene HCN HOH
 A 
Anhyd. AlCl
B   C  D
3
The structure of D would be [AIPMT (Prelims)-2005]

OH COOH
(1) C COOH (2) CH2–C–CH3

CH3 OH
OH CN
(3) CH2–C–CH3 (4) C CH3

CN OH
Sol. Answer (1)
51. In the conversion of

O
CH = CH – CH2 – C – CH3 X
OH
CH = CH – CH2 – CH
CH3
X is
(1) H2/Pt (2) Zn-Hg/HCl (3) Li/NH3 (4) NaBH4
Sol. Answer (4)
CH2 CH3
NaBH4 CH3
O OH
CH3
52. In Tollen’s test, aldehydes

(1) Are oxidised to acids (2) Are reduced to alcohol
(3) Neither reduced nor oxidised (4) Precipitate Ag+ as AgCl
Sol. Answer (1)
+ –
R – CHO + 2Ag + 3OH
–
R – COO + 2Ag + 2H2O
53. Which of the following compound will undergo self aldol condensation in the presence of cold dilute alkali?
(1) CH  C – CHO (2) CH2 = CH – CHO (3) C6H5CHO (4) CH3CH2CHO
Sol. Answer (4)
H
will undergo aldol reaction.
O
54. Which of the following compounds will give positive test with Tollen’s reagent?
(1) Acetic acid (2) Acetone (3) Acetamide (4) Acetaldehyde
Sol. Answer (4)
CH3CHO  2Ag  3OH 

 CH3COO  2Ag   2H2O
55. The order of reactivity of carbonyl compounds for nucleophilic addition is
(1) Ar2C = O >R2C = O > ArCHO > RCHO > H2C = O (2) H2C = O > R2C = O > Ar2C = O > RCHO > ArCHO
(3) H2C = O > RCHO > ArCHO > R2C = O > Ar2C = O (4) ArCHO > Ar2C = O > RCHO > R2C = O > H2C = O
Sol. Answer (3)
HCHO > R – CHO > ArCHO > R2C = O > Ar2C = O
56. The oxidation of toluene with CrO3 in the presence of (CH3CO)2O gives a product A, which on treatment with
aqueous NaOH, produces
(1) C6H5COONa (2) 2, 4-diacetyl toluene (3) C6H5CHO (4) (C6H5CO)2O
Sol. Answer (3)
CrO3
CH3 (CH3CO)2O
CHO
57. When aniline reacts with oil of bitter almonds (C6H5CHO) condensation takes place and benzal derivative is
formed. This is known as
(1) Schiff’s base (2) Benedict’s reagent (3) Million’s base (4) Schiff’s reagent
Sol. Answer (1)
C O + H2N
H 
C N
H
Schiff's base
58. Aldol condensation will not take place in

(1) CH3CHO (2) CH3COCH3 (3) HCHO (4) CH3CH2CHO
Sol. Answer (3)
HCHO  OH 
 No Aldol
59. The oxidation of toluene to benzaldehyde by chromyl chloride is called

(1) Etard reaction (2) Reimer-Tiemann reaction
(3) Wurtz reaction (4) Cannizzaro’s reaction
Sol. Answer (1)
etard reaction
CH3 CHO
60. Polarisation in acrolein can be described as

δ δ δ δ δ δ δ δ
(1) C H  CH  C HO (2) C H  CH  C HO (3) C H  CH  CH O (4) C H  CH  CH O
2 2 2 2
Sol. Answer (4)
+ –
CH 2 = CH – C = O CH2 – CH C–O
H H
61. First product of the reaction between RCHO and NH2NH2

(1) RCH = NNH2 (2) RCH = NH (3) RCH2NH2 (4) RCON3
Sol. Answer (1)
R – C = O + NH2 – NH2 R – C = N – NH2
H H
62. Which of the following is correct?

(1) On reduction, any aldehyde gives secondary alcohol
(2) Reaction of vegetable oil with H2SO4 gives glycerine
(3) Ethyl alcohol and iodine with NaOH gives iodoform
(4) Sucrose on reaction with NaCl gives inverted sugar
Sol. Answer (3)
CN
H3O
63. + CH3MgBr P
OCH3
Product ‘P’ in the above reaction is
OH O
CHO COOH
CH – CH3 C – CH3
(1) (2) (3) (4)

OCH3 OCH3
OCH3 OCH3
Sol. Answer (2)
O
CN
CH3
H3O
+ CH3MgBr
OCH3
OCH3
H . OH
64. In this reaction CH3CHO + HCN  CH3CH(OH)CN   CH3CH(OH)COOH an asymmetric centre is generated.
The acid obtained would be
(1) D-isomer (2) L-isomer
(3) 50% d + 50% l-isomer (4) 20% d + 80% l-isomer
Sol. Answer (3)
OH
65. A and B in the following reactions are R–C–R HCN/ B
A R—C
KCN
O R CH2NH2
CN
(1) A = RRC , B = H3O
OH
CN
(2) A = RRC , B = H2O/OH
OH
(3) A = RRCH2CN , B = NaOH
CN
(4) A = RRC , B = LiAlH4
OH
Sol. Answer (4)
OH OH
HCN B
R C R + R C R R C R
KCN LiAlH4
O CN CH2 NH2
66. Compound A has a molecular formula C2Cl3OH. It reduces Fehling’s solution and on oxidation, it gives a
monocarboxylic acid B. If A is obtained by the action of chlorine on ethyl alcohol, then compound A is
(1) Methyl chloride (2) Monochloroacetic acid (3) Chloral (4) Chloroform
Sol. Answer (3)
Charly, answer is Chloral.
67. Which one of the following on treatment with 50% aqueous sodium hydroxide yields the corresponding alcohol
and acid?
(1) C6H5CHO (2) CH3CH2CH2CHO (3) CH3 – C – CH3 (4) C6H5CH2CHO
Sol. Answer (1)

50% – +
CHO NaOH
COO Na +
OH
68. An ester (a) with molecular formula, C9H10O2 was treated with excess, of CH3MgBr and the complex, so formed,
was treated with H2SO4 to give an olefin (b). Ozonolysis of (b) gave a ketone with molecular formula C8H8O which
shows +ve iodoform test. The structure of (a) is
(1) H3COCH2COC6H5 (2) C2H5COOC6H5
(3) C6H5COOC2H5 (4) p-H3CO  C6H4  COCH3
Sol. Answer (3)

O OH
+
CH3 H
C – O C2H5 + CH3MgBr C C CH2
CH3 CH3
O3, Zn
O
C – CH3 + HCHO
SECTION - D
Assertion-Reason Type Questions
1. A : Aromatic aldehydes are less reactive than aliphatic aldehyde towards nucleophilic addition reaction.
R : In case of aromatic aldehyde, steric hinderance and –I effect of phenyl ring is present.
Sol. Answer (3)
Aromatic aldehydes are less reactive than aliphatic aldehyde towards nucleophilic addition reaction because
of +M effect of benzene decreases the positive charge density on its carbonyl carbon of aromatic aldehyde.
O O
C C
H R H
+ 1 + 2
t t
ec ec
eff eff
+I
+M
Order of the charge +1 < +2
on carbonyl carbon
O O
C > C
 Order of nucleophilic R H H addition reaction.
2. A : In crossed Cannizzaro's reaction in between HCHO and C6H5CHO, HCHO is oxidised.

R : OH– firstly attacks on HCHO. So, HCHO is oxidised.
Sol. Answer (1)
As positive charge density on carbonyl carbon of is more,
 OH– first attacks on it and hence is oxidised.
3. A : HCOOH has less pKa than C6H5COOH.

R : In C6H5COOH, C6H5– group shows –I effect not +R effect.
Sol. Answer (3)
Acidic strength order HCO2H > C6H5CO2H
 Ka order HCO2H > C6H5CO2H { But C6H5 – group shows +I & +R effect }
So, pKa order HCO2H < C6H5CO2H
O
||
4. A : H2N—C—CH3 can give iodoform reaction.
O
||
R : Cl—C—CH3 can also give iodoform reaction due to presence of –COCH3 group.
Sol. Answer (4)

Both of them do not give iodoform reaction because both have gp NH2, & Cl which do not allow haloform
reaction.
5. A : 2-methyl propanal can give Cannizzaro reaction as well as aldol condensation.

R : It has -hydrogen atom.
Sol. Answer (2)
Because of presence of two –CH3 group on -‘C’ the -‘H’ is less acidic. So, it also gives Cannizzaro
reaction.
6. A : Primary alcohols on oxidation give aldehydes.

R : Aldehydes can be oxidized into the corresponding carboxylic acids.
Sol. Answer (2)
P.C.C. KMNO4
R CH2 OH
O.A.
7. A : Ethanal undergoes aldol condensation.

R : Ethanal has four -H atoms.
Sol. Answer (3)
; Ethanol undergoes aldol condensation reaction but it have only 3-H atom.
8. A : Formaldehyde undergoes Cannizzaro reaction in the presence of H.

R : Formaldehyde has two -Hydrogen atoms.
Sol. Answer (4)
O
C , Formaldehyde undergoes Cannizzaro reaction in presence of base, as it zero -‘H’.
H H
9. A : Esters on reduction with LiAlH4 forms alcohols.

R : Esters having at least two -Hydrogen atoms undergo Claisen condensation.
Sol. Answer (2)
O
LiAlH4
C R CH2 OH + R OH
R OR
10. A : Phenol is more acidic than ethanol.

R : Phenoxide ion is resonance stabilized.
Sol. Answer (1)
–
– O
O
> H3C CH2
Stability order of conjugate base
Resonance stabilized
 Acidic strength order
OH
> H 3C CH2 OH
11. A : Ethanol undergoes haloform reaction.

R : Ethanol can be oxidised into ethanal.
Sol. Answer (2)
OH
Because ethanol have 3 -‘H’ and I2 + NaOH is oxidising agent also, which oxidises to
H3C CH2
ethanol and hence halform reaction takes place.
12. A : Nitration of benzoic acid gives ortho and para derivatives of nitrobenzoic acids.
R : Carboxyl group is activating group.
Sol. Answer (4)
–CO2H is a deactivator because of its –M effect it gives meta product.
13. A : Aldehydes and ketones undergo nucleophilic addition reaction.

R : Aldehydes and ketones contain carbonyl group.
Sol. Answer (1)
Carboxyl group undergoes nucleophilic addition reaction.
14. A : Benzaldehyde is more reactive towards nucleophilic addition than acetaldehyde.

R : Benzaldehyde has less steric hindrance than acetaldehyde.
Sol. Answer (4)
O
O
C
C
H
H3C H
Order of nucleophilic addition reaction
t
t ec
eff
ec eff
+I +M
15. A : Benzaldehydes do not give possitive Fehling test.
R : Aldehydes give positive Tollen's test.
Sol. Answer (2)
Aldehydes are easily oxidised to acid because of presence of ‘H’ atom on carbonyl carbon which can be
converted into –OH group, without involving the cleavage of any other bond.
 But aromatic aldehyde (benzaldehyde) however do not reduce Fehling solution or Benedict solution. The
weaker oxidising agent. like Fehling's solution (or Benedict solution) fail to oxide benzaldehyde because the
C – H bond in aldehyde is strong (due to the increase of electron density in C – H bond of the aldehyde group)
and hence stronger oxidising agent are required.
16. A : Hydration of chloral gives a stable product.

R : It is due to high molecular weight.
Sol. Answer (3)
O O
H2O
Cl3C C Cl3CH + C
H HO H
17. A : Acetate ion is less basic than the methoxide ion.

R : The acetate ion is resonance stabilized.
Sol. Answer (1)
Acetate ion is less basic than methoxide ion because acetate ion is resonance stablised.

Stability order >
1
As basic strength order 
Stablity order
So, basic strength order >
18. A : Ozonolysis of benzene gives ethanal.

R : Benzene is an antiaromatic compound.
Sol. Answer (4)
(i) O3
3
(ii) Zn/H2O
Benzene is an aromatic compound.
19. A : Basic hydrolysis of ester is bimolecular in nature.

R : Acidic hydrolysis of ester is pseudo first order reaction.
Sol. Answer (2)
Basic hydrolysis of ester.
Acidic hydrolysis of order
As nucleophilicity order OH– > H2O

 We need to take H2O in large amount to form the product as nucleophilicity of H2O is less. Because of
this, the rate of hydrolysis of ester in acidic medium become independent of [H2O], so it is pseudo first order
reaction.
20. A : Formic acid is the strongest mono carboxylic acid.

R : Trifluoroacetic acid is weaker than formic acid.
Sol. Answer (4)
Acidic strength order .
Because of strong - I effect of ‘3’ ‘F’ atom. at  – c, its conjugate base is more stable.
S.O of conjugate base.


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Chapter 12

Aldehydes, Ketones and Carboxylic Acids

(Nomenclature and Methods of Preparation of Aldehydes and Ketones)

Sol. Answer (2)

The general formula of aldehyde and ketone is CnH2nO.

2. The IUPAC name of following structure is

Sol. Answer (1)

3. IUPAC name of CCl3CHO is

Sol. Answer (4)

4. Which of the following is mixed ketone?

This is mixed ketone.

(1) RCH2OH (2) RCOOH (3) RCHO (4) RCH3

6. Dry heating of calcium acetate gives

(1) Hg+2 (2) KMnO4 (3) KClO3 (4) K2Cr2O7

8. Which of the following pathways produces 2-hexanone?

Sol. Answer (1)

11. Select the reagent for the following reaction.

OHC — (CH2)4 — CHO

(1) SeO2 (2) O3, Zn/H2O

X Must be O3, Zn/H2O

12. Acetyl chloride is reduced with LiAlH4, the product formed is

13. Which factors will increase the reactivity of C O group?

Sol. Answer (1)

16. The correct order of reactivity of PhMgBr towards given compounds

17. Predict the product

In the above sequence of reactions A and B are

21. Aldol condensation will not be observed in

22. Which of the following gives aldol condensation reaction?

(3) CH3 CH2 — C— CH3 (4) (CH3 )3 C — C— C(CH3 )3

Sol. Answer (3)

CH3 CH2 C CH3 have  hydrogen. So it will given aldol reaction.

23. The diketone

on intramolecular aldol condensation gives the final product

Sol. Answer (3)

Sol. Answer (4)

Sol. Answer (3)

It is an example of intermolecular Cannizzaro reaction.

CHO (i) conc. NaOH

COOH COOH COOH CH2OH

29. Dimethyl ketones are usually characterised through

Sol. Answer (3)

(Nomenclature and Methods of Preparation of Carboxylic Group)

33. The IUPAC name of phthalic acid

34. Saponification of ethyl benzoate with caustic soda as alkali gives

Sol. Answer (2)

36. Acetic acid is obtained when

37. Which of the following is optically active?

40. Which of the following aromatic acids is most acidic?

COOH COOH COOH COOH

(1) CH3COCH3 (2) CH3CHO (3) (CH3CO)2O (4) CH4

42. Which one of the following orders of acid strength is correct?

Stability order of CB’s R  CO2  OH  R  O  C  CH

 Acidic strength order R  CO2H  H2O  R  OH  HC  CH

44. The correct order of acidic strength of the carboxylic acid is

46. Treatment of benzoic acid with Cl2/FeCl3 will give

48. The reaction,

50. Identify the wrong statement from the following.

(1) O = CH—CH2—C—(CH2)4—CHO (2)

Sol. Answer (3)

4. In the following sequence of reactions

the end product (C) is

(Physical and Chemical Properties of Aldehydes and Ketones)

SeO2 HIO4 CaO