Question Details

Observe the following reaction sequence:

C4H8 (A) → HCl → C4H9Cl (B) → NH3 → C4H9NH2 (C) (Optically active)


C4H9NH2 → NaNO2 + HCl → C4H9OH

Which of the following is correct structure of A, B and C?

Options

A

.

B

.

C

.

D

.

Show Answer

Correct Answer :

Option D

.

Option 4

Solution :

The correct option is Option 4 (represented by the structures in the fourth image).

Step-by-Step Explanation:

1. Identification of Compound A:
The starting compound A has the molecular formula C4H8, which indicates it is an alkene. Based on the options, A can be either 1-butene or 2-butene.

2. Reaction of A with HCl to form B:
When 2-butene (CH3-CH=CH-CH3) reacts with HCl, it undergoes electrophilic addition to yield 2-chlorobutane (B):
CH3-CH=CH-CH3+HClCH3-CH2-CH(Cl)-CH3

3. Reaction of B with NH3 to form C:
When 2-chlorobutane (B) reacts with ammonia (NH3), a nucleophilic substitution reaction occurs, replacing the chlorine atom with an amino group to yield 2-aminobutane (C):
CH3-CH2-CH(Cl)-CH3+NH3CH3-CH2-CH(NH2)-CH3+HCl

4. Optical Activity of Compound C:
The product 2-aminobutane (sec-butylamine) contains a chiral carbon atom at C-2, which is bonded to four different groups: a hydrogen atom (-H), a methyl group (-CH3), an ethyl group (-CH2CH3), and an amino group (-NH2). Because of this asymmetric carbon, 2-aminobutane is optically active, which matches the problem description.

5. Reaction of C with NaNO2 + HCl:
The reaction of primary aliphatic amines with nitrous acid (NaNO2+HCl) forms an unstable diazonium salt, which undergoes hydrolysis to yield the corresponding alcohol, 2-butanol (C4H9OH).

6. Analyzing the Provided Options:
- Option 1 (image_0): Shows A as 1-butene, B as 1-chlorobutane, and C as 1-aminobutane (which is optically inactive).
- Option 2 (image_1): Shows C as 2-butanol instead of the amine.
- Option 3 (image_2): Shows C as 2-butanol instead of the amine.
- Option 4 (image_3): Shows A as 2-butene, B as 2-chlorobutane, and C as 2-aminobutane. This is the correct structural match.

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