PROBLEM 7.7 - Organic Chemistry

Question

Question: Draw the product of nucleophilic substitution with each neutral nucleophile. When the initial substitution product can lose a proton to form a neutral product, draw the product after proton transfer.

a.

b.

Step-by-Step Solution

Answer

a.

b.

Nucleophilic substitution reaction

The reaction that involves the donation and acceptance of electrons from a base and acid is known as an acid-base reaction. It is also known as a nucleophilic substitution reaction.

Reaction of a.

a. The complete reaction is shown below:Attack of the nucleophile on electrophile

In the above reaction, the lone pair of N (Lewis base) donates its electron pair to the electrophilic carbon atom of 1-bromo-3-methylbutane (Lewis acid). Also, the removal of the bromine atom takes place.

 

There is a position charge on the nitrogen atom due to which proton transfer does not take place. Thus, no neutral compound is formed.

Reaction of b.

b. The complete reaction is shown below: Attack of the nucleophile on electrophile

In the above reaction, the lone pair of oxygen (Lewis base) donates its electron pair to the electrophilic carbon atom of 2-chloro-2-methylpropane (Lewis acid). At the same time, the removal of chlorine also takes place.

 Thereafter, the proton is transferred to form 2-methylpropan-2-ol as a product.