Explain how substitution and elimination reactions compete in the same reaction.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) Substitution and elimination reactions always take place in competition. The reaction pathway and the product formed depend on the following factors:
$(i)$ Nature of the substrate
$(ii)$ Strength of the nucleophile
$(iii)$ Strength of the base
$(iv)$ Nature of the solvent
$(v)$ Temperature of the reaction
Nature of substrate and solvents Nature of Nucleophile or Base and Reaction preferred
$3^{\circ}$ alkyl halide,Polar protic solvent Strong nucleophile but weak base: $S_{N}1$
$3^{\circ}$ alkyl halide,Polar aprotic solvent Strong base but weak nucleophile (Heat): Elimination $(E2)$
$3^{\circ}$ alkyl halide,Polar protic solvent Weak base: Elimination $(E1)$
$1^{\circ}$ alkyl halide or methyl,Polar aprotic solvent Strong nucleophile but weak base: $S_{N}2$

High temperature favours elimination reactions,whereas low temperature favours substitution reactions.
In the case of $3^{\circ}$ alkyl halides,$S_{N}1$ is the major product when substitution and elimination reactions compete in the presence of a weak base.
The tertiary butoxide ion is a strong base but a bulky nucleophile. Therefore,it prefers to abstract a proton from a tertiary halide,causing an elimination reaction to form an alkene as the major product. However,if the alkyl halide is primary,the $S_{N}2$ reaction takes place. The ethoxide ion is a strong nucleophile and also a strong base. With a tertiary halide,it causes both elimination and substitution $(S_{N}1)$ reactions; however,the elimination product (alkene) will be major due to the strong basic character of the ethoxide ion. If the alkyl halide is primary,the ethoxide ion causes an $S_{N}2$ reaction.

Explore More

Similar Questions

An unknown compound $A$ has the molecular formula $C_5H_9Cl$. It does not react with $Br_2 / CCl_4$. When treated with a strong base,it gives a compound $B$ with the molecular formula $C_5H_8$,which reacts with $Br_2 / CCl_4$. Ozonolysis of $B$ followed by treatment with dimethyl sulfide gives a compound with the molecular formula $C_5H_8O_2$. What is the structure of $A$?

Difficult
View Solution

Which of the following compounds would react faster with $NaCN$ in an $S_N2$ reaction?

The reactivity order of the following molecules towards $S_N1$ reaction is:
$(I)$ Allyl chloride
$(II)$ Chlorobenzene
$(III)$ Ethyl chloride

The reaction of a mixture of two organic compounds with $Na$ in ether gives $isobutane$ as a product. The two chlorine compounds are:

In the above reaction,the major product '$P$' 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