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Chapter 27: Problem 20

A sample of \((R)-\mathrm{CH}_{3} \mathrm{CH}(\mathrm{Cl}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) reacts with \(\mathrm{CH}_{3} \mathrm{S}^{-}\) in dimethyl sulfoxide, and the resulting solution is optically active. (a) Write the formula of the product. (b) By which mechanism does this nucleophilic substitution reaction occur?

Short Answer

Expert verified
The resulting product of the reaction is \((R)-\mathrm{CH}_3 \mathrm{CH}(\mathrm{SCH}_3) \mathrm{CH}_2 \mathrm{CH}_3\) and the reaction mechanism is by SN2.

Step by step solution

01

Determine the product of the reaction

The given compound contains a chiral carbon atom attached to a chlorine atom. When the compound reacts with the nucleophile \(\mathrm{CH}_3 \mathrm{S}^-\), the latter will replace the chlorine atom in a nucleophilic substitution reaction. The resulting product will thus have the formula \((R)-\mathrm{CH}_3 \mathrm{CH}(\mathrm{SCH}_3) \mathrm{CH}_2 \mathrm{CH}_3\). This means the chlorine atom in the initial compound has been replaced by a \(\mathrm{SCH}_3\).
02

Identify the mechanism involved

In the context of nucleophilic substitution reactions, two main types of mechanisms can occur: SN1 or SN2. The SN1 mechanism is a two-step pathway that involves the formation of a carbocation intermediate, while the SN2 mechanism is a one-step pathway, where the nucleophile simultaneously attacks the substrate and expels the leaving group. Given that the reaction causes inversion of configuration at the chiral center, and the nucleophile is strong, this reaction likely follows an SN2 mechanism.
03

Provide the final answers

The product of the reaction is \((R)-\mathrm{CH}_3 \mathrm{CH}(\mathrm{SCH}_3) \mathrm{CH}_2 \mathrm{CH}_3\) and the mechanism of the reaction is SN2.

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Most popular questions from this chapter

Write equations for the substitution reaction of \(n\) -bromopentane, a typical primary haloalkane with the following reagents: (a) \(\mathrm{NaN}_{3};\) (b) \(\mathrm{N}\left(\mathrm{CH}_{3}\right)_{3};\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CNa};\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SNa}\).

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