Stereochemistry of SN1 Reaction

Vocabulary flashcards covering the stereochemistry and mechanism of SN1 reactions based on the lecture material.

Stereochemistry of $SN1$

The stereochemical outcome of an $SN1$ reaction yielding a mixture of enantiomers ($R$ and $S$) forming a racemic mixture, where retention is $<50\%$ and inversion is $>50\%$.

Retention of Configuration

The outcome in an $SN1$ reaction where the nucleophile attacks from the same side as the leaving group, constituting less than $50\%$ ($<50\%$) of the product mixture.

Inversion of Configuration

The outcome in an $SN1$ reaction where the nucleophile attacks from the opposite side of the leaving group, constituting more than $50\%$ ($>50\%$) of the product mixture.

Step 1 of $SN1$ Mechanism

The rate-determining step (RDS) involving the slow dissociation of $(CH_3)_3C-Cl$ to yield a stable, $sp^2$ hybridized $3^\circ$ carbocation $(CH_3)_3C^+$ and a leaving group $Cl^-$.

Polar Protic Solvent in $SN1$

A solvent such as $H_2O$ that facilitates the formation and stabilization of the carbocation intermediate, subsequently acting as a nucleophile in Step 2.