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Chapter 27: Problem 17

A sample of \((S)-\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Cl}\) is hydrolyzed by water, and the resulting solution is optically inactive. (a) Write the formula of the product. (b) By which nucleophilic substitution reaction mechanism does this reaction occur?

Short Answer

Expert verified
The product's formula is CH3CH2CH(CH3)OH, but as a racemic mixture, and the type of nucleophilic substitution reaction mechanism involved is SN1 because a racemic mixture is formed.

Step by step solution

01

Identify the Starting Compound

The starting compound mentioned here is (S)-CH3CH2CH(CH3)Cl, a chiral compound consisting of a chiral center marked by the carbon atom bonded to a hydrogen, a methyl group, an ethyl group, and a chloride.
02

Perform the Hydrolysis

The hydrolysis of a compound involves a reaction with water. In this case, the starting compound reacts with water, leading to the replacement of the chloride atom by a hydroxyl group (OH). This results in the following compound: CH3CH2CH(CH3)OH.
03

Identify the Product's Optically Activity

Given that the resulting compound is optically inactive, that implies that the product is achiral. This could mean either an achiral molecule or a racemic mixture. Considering that the starting compound has a chiral center (caused by the 4 different groups attached to the carbon) and the product still retains this carbon center with four different constituencies (H, OH, CH3, and CH2CH3), the product itself likely remains chiral. The optical inactivity would, therefore, suggest that a racemic mixture, an equal mixture of enantiomers, is formed.
04

Determine the Type of Nucleophilic Substitution

Given that the product is an equal mixture of enantiomers (racemic mixture), this infers that the nucleophilic substitution mechanism involved is SN1. This is due to the fact that the SN1 mechanism involves a carbocation intermediate which can be attacked from either side by the nucleophile, forming an equal mixture of enantiomers.

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