Explain the stereochemistry of $S_{N}1$ reaction with a suitable example.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) In an $S_{N}1$ reaction,if the substrate (i.e.,alkyl halide) is optically active,it results in partial racemisation.
The carbocation formed as an intermediate is planar,allowing the nucleophile to attack from either side.
If the nucleophile attacks from the same side as the leaving group,retention of configuration occurs.
If the nucleophile attacks from the opposite side of the leaving group,inversion of configuration occurs.
Since the attack from the opposite side is slightly more favourable,the product is a mixture of enantiomers in unequal amounts,leading to partial racemisation.
If the enantiomers are obtained in a $50:50$ proportion,it is called a racemic mixture,which is optically inactive and denoted as $(\pm)$.
Example: The hydrolysis of optically active $2-$bromobutane results in the formation of $(\pm)-$butan$-2-$ol.

Explore More

Similar Questions

Which of the following,on heating with aqueous $KOH$,produces acetaldehyde?

$n$-propyl bromide on treatment with ethanolic potassium hydroxide produces

Which of the following compounds gives the same $S_N1$ and $S_N2$ product?

Difficult
View Solution

When $CH_3CH_2CHCl_2$ is treated with $NaNH_2$,the product formed is

The major product of the following reaction is:

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo