C HE M IS T R Y

MAHA YUDH
DPP -1
BATCH ST
CLASSROOM PRACTICE PROBLEMS

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ALDEHYDE, KETONE & CARBOXYLIC ACID

Type-1 (Nucleophilic Addition)

1. The increasing order of the following compounds towards HCN addition is
H3CO CHO CHO
(i) (ii)
NO2
CHO O2N CHO
(iii) (iv)
OCH3
[JEE Main 2020]
(1) (i) < (iii) < (iv) < (ii) (2) (iii) < (iv) < (i) < (ii)
(3) (iii) < (iv) < (ii) < (i) (4) (iii) < (i) < (iv) < (ii)

2. In the following reaction,

HCl
Aldehyde + Alcohol   Acetal
t
HCHO BuOH
CH3CHO MeOH
The best combination is
(1) CH3CHO and MeOH (2) CH3CHO and tBuOH
(3) HCHO and MeOH (4) HCHO and tBuOH

O O
Ethylene Glycol
3. +
A
OC2H5 H (Major Product)
The product "A" in the above reaction is :
OH
O O O
(1) OH (2) O O
OC2H5 OC2H5
O
OC2H5 O
(3) (4) O O
OH
OH
 Type-2 (Grignard Reagent)
4. The product formed in the first step of the reaction of
Br
CH3–CH2–CH–CH2–CH–CH3 with excess Mg/Et2O(Et = C2H5) is: [JEE Main 2021]

Br

(1) CH3–CH2–CH–CH2–CH–CH3 (2) CH3–CH2–CH–CH2–CH–CH3

CH3–CH–CH2–CH–CH2–CH3 CH3–CH2–CH–CH2–CH–CH3

MgBr
CH2
(3) CH3–CH (4) CH3CH2–CH–CH2–CH–CH3
CH–CH3
MgBr

CN
5. (i) C 6H5MgBr Ether (1.0 equivalent ), dry
 (ii) H O
3
 X Major Product

OCH3
The structure of X is :

(1) NH2 (2) NH2

C6H5 OCH3
O O

C6H5 C6H5
(3) (4)
C6H5

C6H5 OCH3

6. Reaction of Grignard reagent, C2H5MgBr with C8H8O followed by hydrolysis gives compound
"A" which reacts instantly with Lucas reagent to give compound B, C10H13Cl.
The Compound B is :
Cl
CH3

(1) CH3 (2)

Cl

CH3 Cl CH3
Cl
(3) CH3 (4) CH3
7. Choose the correct option(s) for the following set of reaction [Adv. 2018]
(i) MeMgBr Conc.HCl
C6H10O Q S
(ii) H2O
(major)
20% H3PO4, 360 K

(i) H2, Ni HBr, benzoyl peroxide

T R U
(major) (ii) Br2, h (major)  (major)
CH3 H3C H3C Br CH3
Br
Cl Cl
(1) (2)

S T U S
H3C Cl CH3 CH3 H3C Br
Br Br
(3) (4)

S U U S

8. Choose the correct option(s) from the reaction below :

Ph — CH  CH — C — H (1) CH CH MgBr
(2) H O
 X Cu, 
3
Y 2

|| 3

O
(1) X is 1, 4-addition product ; Y is Ph — C — CH CH — CH2 — CH3
||

O
(2) X is 1, 2-addition product ; Y is Ph — CH CH — C — CH2 — CH3
||

O
(3) X is 1, 4-addition product; Y is Ph — CH CH — C — CH2 — CH3
||

O
(4) X is 1, 2-addition product, Y is Ph — C — CH CH — CH2 — CH3
||

O

9. Point out the following incorrect Grignard synthesis.

OH
Br CH–Ph
(i) Mg, ether
(ii) PhCH=O
(1) N N
(iii) H3O
H H
O O O O
(i) Mg, ether
(2) (ii) PhCH=O
Br (iii) H3O HOCH2
O
MgBr
(3) CH3–C–CH3 OH
H3O
O HO CH2CH3
(i) CH3CH2MgBr
(4) ether
(ii) H3O
OH OH
 Type-3 (Oxidizing Reagent Based)
10. Which of the following reagent is used for the following reaction ? [JEE Main 2021]
?
CH3CH2CH3   CH3CH2CHO
(1) Manganese acetate (2) Copper at high temperature and pressure
(3) Molybdenum oxide (4) Potassium permanganate

11. The major product of the following reaction is:

H /CO
CH3CH2CH = CH2 2
Rh catalyst

(1) CH3CH2CH=CH–CHO (2) CH3CH2C=CH2
CHO
(3) CH3CH2CH2CH2CHO (4) CH3CH2CH2CHO]

12. Given below are two statements :

Statement-I : 2-methylbutane on oxidation with KMnO4 gives 2-methylbutan-2-ol.
Statement-II : n-alkanes can be easily oxidised o corresponding alcohol with KMnO4.
Choose the correct option :
(1) Both statement I and statement II are correct
(2) Both statement I and statement II are incorrect
(3) Statement I is correct but Statement II is incorrect
(4) Statement I is incorrect but Statement II is correct

Type-4 (Reducing Agent Based)

13. ?

O
Which of the following reagent is suitable for the preparation of the product in the above
reaction ? [JEE Main 2021]
 
(1) NaBH4 (2) NH2–NH2/ C2H5 ONa
(3) Ni/H2 (4) Red P + Cl2

O
O
14. i) DIBAL H, Toluene, 78ºC

ii) H O
 "P "
3 (Major Pr oduct )

The product "P" in the above reaction is :

OH

(1) COOH (2) CHO

O–C–H

(3) (4) CHO

15. Which one of the following reactions will not form acetaldehyde?
Cu (i)DIBAL H
(1) CH3CH2OH  573 K
 (2) CH3CN  (ii)H O
 2

Pd(II)/Cu(II) CrO3 H2SO4

(3) CH2 = CH2 + O2 
 H2 O
(4) CH3CH2OH 

 Type-5 (Aldol and Intramoleculer Aldol)
16. Identify A in the given chemical reaction,
CH2CH2CHO NaOH
A (Major product) [JEE Main 2021]
C2H5OH, H2O, 
CH2CH2CHO

CHO CH2CH2COOH
(1) (2)
CH2CH2CH2OH
O
C–H O
(3) (4)
O

17. The major product formed in the following reaction is

O CH3
O
dil. NaOH
H3C H +

O OH OH O

H3C H3C
(1) (2)

O OH
OH O
H H3C
(3) H C H (4)
3

18. The major product obtained in the following reaction is

CH3 O
NaOH
OHC 
CH3 CH3

CH3 H3C
(1) H (2) H (3) (4)
O CH3 O CH2 O O

19. In the following reactions, products A and B are

O O
Dil. NaOH H3O+
H 3C H [A] 
[B]
H3C CH3

O O

(1)
CH3 CH3
A= CH3 ; B= CH3
HO
 O O

(2)
CH3 CH3
A= CH3 ; B= CH3
HO
O
O
OH C CH3
H3C H H
(3) A= ; B=

H3C H3C
CH3 CH3
O
O
OH C H2C
H H
A= H3C ; B=
(4)
H3C H3C
CH3 CH3

20. The desired product X can be prepared reacting the major product of the reactions in List-I
with one or more appropriate reagent in List-II.
(Given, order of migratory aptitude : aryl > alkyl > hydrogen) [Adv. 2019]
O
Ph
OH
Me Ph
X
List-I List-II
Ph
HO
(P) Me + H2SO4 (1) I2, NaOH
Ph
OH
Me
Ph
H2N
(Q) H + HNO2 (2) [Ag(NH3)2]OH
Ph
OH
Me
Ph
HO
(R) Ph + H2SO4 (3) Fehling solution
Me
OH
Me
Ph
Br
(S) H + AgNO3 (4) HCHO, NaOH
Ph
OH
Me
(5) NaOBr
The correct option is
(1) P  1; Q  2, 3; R  1, 4; S  2, 4 (2) P  1, 5; Q  3, 4; R  4, 5; S  3
(3) P  1, 5; Q  3, 4; R  5; S  2, 4 (4) P  1, 5; Q  2, 3; R  1, 5; S  2, 3
 Type-6 (Cannizaro Reaction)
21. Identify A in the following chemical reaction
CHO
(i) HCHO,NaOH
A
(ii) CH3CH2,Br,NaH, DMF [JEE Main 2021]
CH3O (iii) HI, 

O
C–OCH2CH3 CH2OH

(1) HO (2) CH3O

CH2I CH2OH

(3) HO (4) HO

22. Major products of the following reaction are

CHO
(i) 50% NaOH
+ HCHO
(ii) H3 O+

COOH
(1) CH3OH and HCO2H (2) CH3OH and

CH2OH CH2OH COOH

(3) HCOOH and (4) and

23. Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the
products contains sodium trichloroacetate ion and another compound. The other compound is
(1) 2, 2, 2-trichlorethanol (2) trichloromethanol
(3) 2, 2, 2-trichloropropanol (4) chloroform

24. The major product of the following reaction sequence is: [Adv. 2016]
O
(i) HCHO (excess)/NaOH, heat
+
(ii) HCHO/H (catalytic amount)

O O O O OH

(1) (2)

O O O OH
HO
(3) (4)

OH
25. Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of
Q and S is C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S
undergoes haloform reaction but not Cannizzaro reaction.
(i) P 
(i)O 3 /CH2Cl2
(ii) Zn/H O
Q
2 (C8H 8O)

(ii) R 
(i)O 3 /CH2Cl2
(ii) Zn/H O
S
2 (C8H 8O)

The option(s) with suitable combination of P and R, respectively, is (are)

H3C
CH3 CH3
(1) H3C and (2) and
CH3 CH3
H3C

H3C CH3
CH3 CH3
and
(3) CH3 (4) H3C and H3C
CH3 CH3

Type-7 (Acid and it’s derivations)

26. The decreasing order of ease of alkaline hydrolysis for the following esters is

COOC2H5 Cl COOC2H5 O2N COOC2H5 CH3O COOC2H5

I II III IV
(1) III > II > IV > I (2) III > II > I > IV (3) II > III > I > IV (4) IV > II > III > I

27. The major product obtained in the following reaction is

CO2Et
NaOEt/
O
O
O

O
(1) (2) CO2Et
CO2Et
O

O
(3) (4) CO2Et
CO2Et
 ANSWER KEY
1. (4) 2. (3) 3. (2) 4. (4) 5. (4)
6. (3) 7. (1,4) 8. (2) 9. (1,2,4) 10. (3)
11. (3) 12. (3) 13. (2) 14. (2) 15. (4)
16. (3) 17. (3) 18. (3) 19. (2) 20. (4)
21. (3) 22. (3) 23. (1) 24. (1) 25. (1,2)
26. (2) 27. (2)

SOLUTION
O O OH O
3. OH
O O C2H5
OC2H5 H
+ O

Br Br MgBr MgBr

4. Mg(Excess)

(dry ether )


Ph
+
CN – + C=N–MgBr
PhMgBr
5. Dry ether

OCH3 OCH3
H3O+

Ph Ph

C=N C=NH Br
+
H3O
+Mg
OH
OCH3 OCH3

10. MO2 O3
CH3–CH2–CH3   CH3–CH2–CH=O
The reagent used will be MO2O3

11. OXO PROCESS (Hydroformylation) :

Rh
CH3–CH2–CH = CH2 + CO + H2 
catalyst
 + CHO
CHO (Major)

12. Alkane are very less reactive, tertiary hydrogen can oxidise to alcohol with KMnO4.
H KMnO4 OH

2-methyl-butane
 (i) NH2–NH2
13. (ii) EtO–Na+/
O
To reduce the carbonyl groups into alkane wolf – kischner reduction is used, without affecting
the double bond.

O H
O OH C=O

(i) DIBAL-H
(ii) H3O
14.
DIBAL cannot reduce double bond It can reduce cyclic ester.

O
15.
CrO3 .H2SO4
CH3CH2OH   CH3–C–OH
Strong oxidising agent
(Carboxylic
acid is formed
by complete
oxidation)

O
CH2–CH–C–H
OH–
16. H
CH2–CH2–C–H
O O
2
CHO 3 1
H
H 
7 H
OH 4 6
5
O
C2H5OH/
CHO
–H2O
 O
C–H

NaOH 
21. + H–C–H Cannizaro H–C–ONa + H3CO CH2–OH

O O
OCH3
CH3–CH2–Br

H3C – O CH2 – O–CH2–CH3

I–H I–H

HI 

CH2–I

+ CH3–I+CH3–CH2–OH

 HI
OH
CH3–CH2–I