Chemistry

ALDEHYDE PREPARATION
JEE main - Chemistry

C2 H5 O

1. X −−−−→
⊕
H O
3

Find correct structure of X:

a) b)

c) d)

na
2. In the given reaction

−
−
H

−→
2

⊕
O

(P) + (Q)
ata
kh
Identify P and Q:
rav

a) b)
and and

c) d) All of these
u

and
Ga

3. Which of the following reagents may be used to accomplish the conversion?

C6H5CH = CH - CH2OH ⟶ C6H5CH = CHCHO

a) b) [(CH3)3 CO]3 Al,

c) All of these d) MnO2

4. Which one of the following combinations gives compound (X)?

a) b)

c) d)

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5. Formonitrile on treatment with ethyl magnesium chloride in presence of dry ether and subsequent hydrolysis gives
________.

a) propanone b) butan-2-one

c) butanal d) propanal
CrO2 C l2 in H2 , Pd - BaS O4

6. X −−−−−−−→ C6H5-CHO ←−−−−−−−− Y. Predict X and Y.

+
C S2 , H3 O quinoline

a) X = C6H5CN b) X = C6H5CH3

Y = C6H5COOCH3 Y = C6H5COCl

c) X = C6H5CH2OH d) X = C6H5COOH
Y = C6H5CH2CN Y = C6H5CH2CH3

na
7. In the following reaction A is:

ata
kh

a) b)
u rav

c) d)
Ga

8. Identify compound (A) in the following reaction:

H2 /P d/H aSO4

A −−−−−−−−→

a) Acetophenone b) Benzoyl chloride

c) Toluene d) Benzoic acid

9. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis?

a) b)

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 c) d)

na
10. Compound A on treatment with alcoholic KOH forms compound B. B further undergoes reductive ozonolysis to form C
and D. Both C and D are capable of undergoing oxidation with Tollen’s reagent to form isovaleric acid and formic acid
respectively. Predict the structure of A.

a) ata b)
kh
c) d)
rav

11. An alkene X (C3H6) undergoes reductive ozonolysis in dichloromethane to form products Y and Z. The mixture of Y

and Z together are treated with dilute NaOH solution followed by dehydration to form W. Predict the structure of W.

a) b)
u
Ga

c) d)

12. Compound A, C8H10O, is found to react with NaOI (produced by reacting Y with NaOH) and yields a yellow precipitate
with characteristic smell. A and Y are respectively ________.

a) b)
- OH and I2
- CH3 and I2

c) d)

and I2 - CH2 - OH and I2

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13. The products obtained in the reaction
C onc. NaOH

−−−−−−−→ Products:
Δ

a) PhCHO and HC OO ⊖
Na
⊕
b) P hC OO
⊖
Na
⊕
, PhCH2OH and
⊖ ⊕
HC OO Na

c) Ph - CH2OH and CHCl3 d) Ph— CHO and CHCl3

14. A compound (A), C4H8C12, on hydrolysis gives a product (B) which forms a 2, 4-DNP derivative, but does not reduce

Tollen’s reagent. The compound (A) has the structure:

a) CH3CH2CH2CHCl2 b) CH3CH2CCl2CH3

c) CH3CH2CHClCH2Cl d) CH3CHClCHClCH3

O3 KOH , Δ

15. −−−−−→ A −−−−−→ B

Zn−H2 O

a
Compound B is:

tan
a) b)
ha
c) d)
vk

16.

(P) will be:

ura

a) b)

c) d)
Ga

17. Match the following:

Column A Column B
C uC l2

i. CH2 = CH2 + PdCl2 + H2O −−−→ a. Rosenmund reaction

O2

H2 , P d/BaSO4

ii. −−−−−−−−→ b. Etard reaction

quinoline

[H ], SnC l2

iii. −−−−−−−−−→ c. Wacker process

+
conc. H C l, H3 O

C r O2 C l2

iv. −−−−−→ d. Friedel-Crafts acylation

C C l4

e. Stephen reduction

a) i - c, ii - a, iii - e, iv - b b) i - c, ii - d, iii - a, iv - b

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 c) i - e, ii - c, iii - b, iv - d d) i - e, ii - a, iii - c, iv - d
18. Which one of the following alcohols cannot be oxidized by K2CrO4?

a) Isopropyl alcohol b) Ethanol

c) Allyl alcohol d) Tert butyl alcohol

19. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further
treatment with aqueous KOH yields compound F. Compound F is

a) b)

c) d)

na
20. The reagent used in Etard reaction is ________.

a) CrO2Cl2 in CCl4 b) PCC in CH2Cl2

c) CrO3, H2SO4 in CH3COCH3

21. Consider the following sequence of reaction

ata d) CrO3 in (CH3CO)2O
kh
+2
Hg NaN3

P h − C ≡ CH −−−−→ A −−−−→ B(M ajor)

H2 SO4 H2 SO4

The structure of major product B is:

rav

a) b)
u

c) d)
Ga

Δ CHl aq.KOH

22. −−−→ A −−→ B−−−−−→ C ; Product C is:

−C O2

a) b)

c) d)

23. Allyl alcohol → Prop-2-enal. Predict x.

a) COCl2, anhydrous AlCl3, Δ b) CrO2Cl2 in CCl4

c) C5H5NH+CrO3Cl- in CH2Cl2 d) SnCl2/conc. HCl-H3O+

24. Compound X (C4H6) on treatment with two moles of dilute hydrogen bromide forms Y which on alkaline hydrolysis

forms a carbonyl compound Z. Predict X, Y and Z.

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 a) X = Buta-1,3-diene b) X = But-2-yne
Y = 2,3-Dibromobutane Y = 2,2-Dibromobutane
Z = Butanal Z = Butan-2-one

c) X = Buta-1,3-diene d) X = But-1-yne
Y = 1,3-Dibromobutane Y = 2-Bromobut-2-ene
Z = Butane-1,3-diol Z = Butan-2-ol
t
AlO Bu in i. dil NaOH

25. X −−−−−−→ Prop-2-en-1-al ←−−−−−− Y

+
acetone ii.Δ, H

a) X = b)
X=
Y = Methanal + Ethanal Y = 2 moles of ethanal

c) d)
X=
X=

Y = Ethanal + Acetone
Y = 2 moles of methanal

a
26. The intermediate formed in the following reaction is ________.

tan
i. 273 − 283 K

+ CrO3 + (CH3CO)2O −−−−−−−−→ + 2CH3COOH

+
ii. H3 O , heat
ha
a) b)
vk

c) d)
ura

27. Consider the following sequence of reactions.

Ga

Identify A, B, C and D.

a) -Br, COOH, -COCl, -COCH2CH3 b) -Br, -COOH, -COCl, -CHO

c) -F, -COOH, -COCH3, -OCH2CH2CH3 d) -CHO, -COOH, -COCl, -COCH2CH3

2+ +
Hg /H

28. Ph − C ≡ C − CH3 ⟶ A,

Here A is

a) b)

c) d)

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29. The end product in the reaction is:
P2 O5 H2 , Ni H NO2 Cu

CH3CONH2 −−−→ B −−−−→ C −−−−→ D−−→ E

∘
300

a) CH3COCH3 b) CH3CHO

c) (CH3CO)2O d) CH3COOC2H5

30. An unsaturated hydrocarbon X absorbs two hydrogen molecules on catalytic hydrogenation, and also gives the following
reaction:
+
O3 [Ag(N H3 ) ]
2

X −−−−−→ A −−−−−−−→
Zn/H2 O

B(3-oxo-hexanedicarboxylic acid) X will be:

na
a) b)

ata
kh
c) d)
u rav
Ga

31. Which compound would give 5 - keto - 2 - methylhexanal upon ozonolysis?

a) b)

c) d)

32. Compound , formed by the reaction of furfural with ethanol is:

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 a) an aldol b) an acetal

c) a ketal d) a hemiacetal
33. Hydrolysis of isopropylidene chloride using dilute barium hydroxide gives ________.

a) isopropyl alcohol b) propionaldehyde

c) acetaldehyde d) acetone
34. The major products of the following reaction are

a) b)

na
c) atad)
kh

10% NaOH Δ (i) LiAlH4 , Ether Ni

35. 2X −−−−−−→ Y −
→Z− → W −→ P
rav

−−−−−−−−
+
(ii) H2 O/H H2

In above sequence of reaction X is a four carbon organic compound, which can be oxidized by ammoniacal silver nitrate.
Find the structure of W and P.
u

a) b)
Ga

c) d)

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36. In the following reactions, the product S is

a) b)

c) d)

||

37. H 3C − C − Cl + ⟶ Major product:

a) b) O

||

P h − C − N H2

c) d)

na
38. The major aromatic product C in the following reaction sequence will be:
HBr
(e xc e ss)

−−−→ (A) −
Δ
−−−−
(i) KOH (Alc.)

−−−→ B −−

(ii) H
−−−−
+
→ C
O3

ata
Zn/H3 O
+

a) b)
kh
rav

c) d)
u

⊕
H O
3

39. A + 2 Glycerol
Ga

−−−→

Product (A) of the reaction is:

a) b)

c) d)

40. Identify a correct statement from the following:

a) Ketonic group is always present at the b) The pistachio odour of ice cream is due to
terminal carbon of the chain. the presence of vanillin in it.

c) The first oxidation product of a secondary d) The musky aroma derived from musk deer
alcohol is an aldehyde. contains -CO functional group.

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 H O
2

⊕
H

41. −
−−→ (X) .

(X) will be:

a) b)

c) d)

42. Reduction of benzoyl chloride with Pd/BaSO4 produces

a) Benzoic acid b) Benzoyl cyanide

c) Benzene d) Benzaldehyde
43. But-2-enenitrile on reductive hydrolysis using diisobutylaluminium hydride gives ________.

a) but-2-en-1-al b) but-2-en-1-ol

na
c) buten-1-al d) butan-2-one
44. Consider the following sequence of reaction
Hg
+2

Ph - C ≡ CH −−−−→ A −−−−→ B (Major)

H2 SO4

The structure of major product B is:

NaN3

H2 SO4
ata
kh
a) b)
rav

c) d)
u

H O
2

⊕
H

45. In the given reaction

Ga

−
−−→ (P )

P will be:

a) b)

c) d)

H
2

PCC C H3 N H2 Pd−C

46. −−−→ −−−−−→ −−−→ (P )

⊕
H

P will be:

a) b)

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 c) d)

47. The major product of the following reaction is :

(i) Ni/H2

−−−−−−−−−→
(ii) DI BAL−H

a) b)

c) d)

na
48. The major product of the following reaction is ________.

ata
kh
rav

a) b)
u
Ga

c) d)

49. The sequence of reagents required for the following conversion are ________.

a) HCHO, HCN, H O/H+, Ca(OH) , Δ b) K Cr O /OH-, Δ/H O+, Ca(OH) , Δ

2 2 2 2 7 3 2

c) K Cr O /OH-, Δ, Na/C H OH, Conc. d) SOCl2, Mg/dry ether, K2Cr2O7/dil. H2SO4,

2 2 7 2 5

H2SO4/Δ, Br2, KOH(alc) H2O/H+

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50. The end product in the following sequence is:
P2 O5 H2 ,Ni

Acetamide −−−→ (A) −−−→ (B)

a) CH3NH2 b) CH3COONH4

c) CH3CN d) C2H5NH2

na
ata
kh
u rav
Ga

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