Question Details

Consider the following sequence of reactions and find B

Options

A

H2N− (CH2)4 −OH

B

H2N− (CH2)4 −NH2

C

HO − (CH2)4 − OH

D

Correct Answer :

H2N− (CH2)4 −NH2

Solution :

The correct answer is H2N− (CH2)4 −NH2.

Let us break down the reaction sequence step-by-step:

Step 1: Nucleophilic Substitution with Excess Ammonia
In the first step, 1,4-dichlorobutane, Cl−(CH2)4−Cl, reacts with excess ammonia (NH3). Ammonia acts as a nucleophile and undergoes nucleophilic substitution (SN2) at both carbon atoms holding the chlorine leaving groups. Since ammonia is present in excess, the reaction proceeds to form the corresponding diammonium salt, which is intermediate A:
Cl−(CH2)4−Cl+2NH3[H3N+−(CH2)4−NH3]2+2Cl

This intermediate A is the diammonium chloride salt shown in the attached image as H3N+−(CH2)4−NH3+.

Step 2: Neutralization with Sodium Hydroxide (NaOH)
In the second step, the acidic diammonium salt A is treated with a strong base, sodium hydroxide (NaOH). The hydroxide ions (OH) deprotonate the ammonium groups (NH3+) to regenerate the free amine groups (NH2), producing water (H2O) and sodium chloride (NaCl):
[H3N+−(CH2)4−NH3]2+2Cl+2NaOHH2N−(CH2)4−NH2+2H2O+2NaCl

Thus, the final product B is the free diamine, 1,4-butanediamine (also known as putrescine), which corresponds to the formula:
H2N−(CH2)4−NH2

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