A sample of (S)-CH3 CH2 CH(CH3) Cl is hydrolyzed by water, and the resulting solution is optical

step 1 Okay, so we're asked to write the formula of the products and determine by what mechanism this o

A sample of (S)-CH3 CH2 CH(CH3) Cl is hydrolyzed by water,...

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?

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Key Concepts

Nucleophilic Substitution Reaction

This reaction involves the replacement of a leaving group (in this case, chlorine) with a nucleophile (water). Nucleophilic substitution can occur via different mechanisms, and the choice of mechanism depends on the structure of the substrate, the strength of the nucleophile, the leaving group, and the solvent conditions.

SN1 Mechanism

The SN1 (substitution nucleophilic unimolecular) mechanism features a two-step process. First, the leaving group departs, forming a planar carbocation intermediate. Then, the nucleophile attacks the carbocation from either face, which often leads to racemization. This pathway is common when a relatively stable carbocation is formed under polar protic solvent conditions.

Racemic Mixture Formation

Due to the planar structure of the intermediate in the SN1 mechanism, attack by the nucleophile occurs with equal probability from either side. This results in the formation of enantiomers in equal amounts, leading to a racemic (optically inactive) mixture despite starting from an optically active substrate.

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