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

Show Answer

Correct Answer :

Option B

H2N− (CH2)4 −NH2

Solution :

Correct Answer: H2N− (CH2)4 −NH2 (1,4-diaminobutane / putrescine)

To determine the product B, we can analyze the reaction sequence step-by-step from the provided images:

1. Analysis of the Image Data:
- The first image displays the reaction sequence:
Cl-(CH2)4-ClExcess NH3ANaOHB+H2O+NaCl
- The second image shows the structure of the dication:
H3N+-(CH2)4-H3N+
which corresponds to the protonated intermediate salt A (along with two chloride counter-ions, 2Cl-).

2. Step-by-Step Reaction Mechanism:

Step 1: Nucleophilic Substitution with Excess Ammonia
The starting material is 1,4-dichlorobutane, Cl-(CH2)4-Cl. When it is treated with excess ammonia (NH3), ammonia acts as a nucleophile and undergoes nucleophilic substitution (SN2 mechanism) at both chlorine-bearing carbon atoms. Since ammonia is basic, the hydrochloric acid (HCl) produced during substitution protonates the newly formed amine groups. This yields the dihydrochloride salt of 1,4-diaminobutane, which is compound A:
[H3N+-(CH2)4-NH3+]2Cl-

Step 2: Deprotonation with Strong Base (NaOH)
When intermediate salt A is treated with sodium hydroxide (NaOH), a strong base, it undergoes an acid-base neutralization reaction. The hydroxide ions (OH-) deprotonate the ammonium groups (-NH3+), converting them back to free neutral amine groups (-NH2). This releases the free diamine, 1,4-diaminobutane (compound B), alongside water and sodium chloride:
[H3N+-(CH2)4-NH3+]2Cl-+2NaOHH2N-(CH2)4-NH2+2H2O+2NaCl

Thus, compound B is H2N− (CH2)4 −NH2.

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