PROBLEM 7.68 - Organic Chemistry

Question

Question: When a single compound contains both a nucleophile and a leaving group, an intramolecular reaction may occur. With this in mind, draw the product of the following reaction. 

Step-by-Step Solution

Answer

Answer 

The formation of the intramolecular product will take place by the following steps:

The abstraction of the proton by the ^-OH  ion:

Abstraction of the proton

The bromide ion will act as a leaving group, and the carboxylate ion will act as a nucleophile and result in the formation of the following product:

Intramolecular product

Intramolecular substitution reaction

The nucleophilic substitution is the one in which there is a participation of the neighboring group within the molecule.  

The groups within the molecule can act as the nucleophile as well as the leaving group. 

The intramolecular substitution reactions are also stereospecific in nature.

The mechanism of the intramolecular substitution reaction

The given compound is a secondary alkyl halide. The ^-OH  ion will abstract a proton from the carboxylic acid group as shown in the following step:

Abstraction of the proton

The carboxylate ion will act as a nucleophile that is present within the molecule. Due to the negative charge on the carboxylate ion, it will act as a nucleophile. The removal of the leaving group, i.e., the bromide ion, will take place as shown in the following step: 

Intramolecular product

After the removal of the leaving group, the nucleophile carboxylate group will attack, and the intramolecular product will be formed.