A sample of (R)-CH3 CH2 CH(CH3) Cl reacts with CH3 O^- in dimethyl sulfoxide, (CH3)2 SO, a conve

step 1 We are asked to write the formula of the products and determined by what mechanism this occurs.

A sample of (R)-CH3 CH2 CH(CH3) Cl reacts with CH3 O^- in...

A sample of $(R)-\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Cl}$ reacts with $\mathrm{CH}_{3} \mathrm{O}^{-}$ in dimethyl sulfoxide, $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO},$ a convenient solvent for organic reactions. The resulting solution is optically active. (a) Write the formula of the product. (b) By which mechanism does this nucleophilic substitution reaction occur?

A sample of $(R)-\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Cl}$ reacts with
$\mathrm{CH}_{3} \mathrm{O}^{-}$ in dimethyl sulfoxide, $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO},$ a convenient solvent for organic reactions. The resulting solution is optically active. (a) Write the formula of the product. (b) By which mechanism does this nucleophilic substitution reaction occur?

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Key Concepts

SN2 Reaction Mechanism

This is a concerted mechanism in which the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group in a single, simultaneous step. The process results in the inversion of the configuration at the reactive center, meaning that if the starting material is chiral, the stereochemistry will be flipped during the reaction.

Polar Aprotic Solvent Effects

Polar aprotic solvents, such as dimethyl sulfoxide (DMSO), do not form strong hydrogen bonds with anions. This solvent quality enhances the nucleophilicity of anionic species by not solvating them too strongly, thereby facilitating SN2 reactions by making the nucleophile more reactive.

Stereochemical Inversion (Optical Activity)

When a chiral substrate undergoes an SN2 reaction, the inversion of configuration at the center of attack typically results in the optical activity of the product being maintained. The process is often referred to as a 'Walden inversion,' which is crucial for understanding how molecular chirality is manipulated in nucleophilic substitution reactions.

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