On what factors does the rate (reactivity) of the $S_{N}1$ reaction depend? Explain with suitable examples.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The rate of an $S_{N}1$ reaction depends only on the concentration of the substrate. The rate-determining step is the formation of a carbocation. Therefore,the more stable the carbocation formed in the first step,the easier it is for the alkyl halide to form the carbocation,and the higher the rate of the $S_{N}1$ reaction.
$(a)$ Reactivity of $1^{\circ}, 2^{\circ}, 3^{\circ}$ alkyl halides: Tertiary $(3^{\circ})$ halides react fastest in $S_{N}1$ reactions because the $3^{\circ}$ carbocation is the most stable. The order of reactivity is: $3^{\circ} \text{ halide} > 2^{\circ} \text{ halide} > 1^{\circ} \text{ halide}$.
$(b)$ Allylic halides: Allylic halides show high reactivity towards $S_{N}1$ reactions because the allylic carbocation formed in the first step is resonance-stabilized. For example: $CH_{2}=CH-CH_{2}Cl \rightarrow CH_{2}=CH-CH_{2}^{+} + Cl^{-}$.
$(c)$ Benzylic halides: Benzylic halides are highly reactive towards $S_{N}1$ reactions because the benzylic carbocation formed after the departure of $Cl^{-}$ is resonance-stabilized by the benzene ring.

Explore More

Similar Questions

$A$ mixture of an alkyl halide and an aryl halide is treated with sodium in dry ether. What is the name of this reaction?

Among the given pairs,in which pair does the first compound react faster than the second compound in an $S_{N}1$ reaction?

Difficult
View Solution

The chlorine atom of the following compound that reacts most readily with $AgNO_3$ to give a precipitate is

Which of the following alkyl halides gives the most complex mixture of alkenes in an $E_2$ reaction?

Determine the number of chiral products (including stereoisomers) formed upon $E_2$ elimination of the given substrate with $alc. KOH$.

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