Q-21-21-6P - Organic Chemistry (Mcmurry)

Question

The following structure represents a tetrahedral alkoxide ion intermediate formed by the addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product.

Step-by-Step Solution

Answer

The nucleophile is ${\mathrm{OH}}^{-}$.

The leaving group in the molecule is ${\mathrm{CH}}_3{\mathrm{O}}^{-}$. The derivative of starting acid is methyl-2-cyclopentylacetate.

The ultimate products are methanol and cyclopentylacetate anion.

The given species

The representation of alkaline ion using the model as below:

The nucleophilic substitution reaction

In the given reaction, the reacting molecule is shown below:

The nucleophilic attack by the base () hydroxide ion can yield the intermediate. This will lose a methoxyl group and yields 2-cyclopentyl-1-hydroxy-1-methoxyethan-1-olate as the intermediate. Then the leaving group that is acetate leaves the substrate molecule and forms the respective products.

Explanation

The nucleophile is .

The leaving group in the molecule is . The derivative of starting acid is methyl-2-cyclopentylacetate. 

The ultimate products are methanol and cyclopentylacetate anion.