A sample of (R)-CH3 CH(Cl) CH2 CH3 reacts with CH3 S^- in dimethyl sulfoxide, and the resulting

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

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?

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?

Key Concepts

Stereochemical Inversion

Stereochemical inversion refers to the flipping of configuration at the chiral center that occurs during an SN2 reaction. Because the nucleophile attacks from the opposite side to the leaving group, the spatial arrangement of substituents is reversed, which leads to an inversion of the original configuration. This concept is central in understanding the optical activity of the product in chiral molecules.

Polar Aprotic Solvent Effects

Polar aprotic solvents, such as dimethyl sulfoxide (DMSO), stabilize ions through dipole interactions without forming strong hydrogen bonds with anions. These solvents enhance the reactivity of nucleophiles by not overly solvating them, which promotes the SN2 reaction mechanism. The choice of solvent can significantly influence reaction rates and mechanistic pathways in nucleophilic substitution reactions.

Nucleophilic Substitution

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. This class of reactions is fundamental in organic chemistry, where a molecule undergoes a structural change by exchanging one of its substituents. The reaction typically follows distinct mechanistic pathways, often classified as SN1 or SN2, each with different kinetics and stereochemical outcomes.

SN2 Reaction Mechanism

The SN2 (bimolecular nucleophilic substitution) mechanism is a one-step process where the nucleophile attacks the electrophilic center simultaneously as the leaving group departs. This mechanism is characterized by a backside attack, leading to a concerted reaction with inversion of stereochemistry at the carbon center. SN2 reactions are sensitive to steric hindrance and are favored by primary substrates and strong nucleophiles.

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