Why is the alkyl halide shown below not capab | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(D) For an $E2$ reaction to occur,the leaving group $(Br^-)$ and the $\beta$-hydrogen must be in an anti-periplanar orientation ($180^\circ$ dihedral

Vedclass · Accepted Answer

The $C-H$ and $C-Br$ bonds which need to break cannot achieve an anti-periplanar orientation.

Vedclass · Answer

(D) For an $E2$ reaction to occur,the leaving group $(Br^-)$ and the $\beta$-hydrogen must be in an anti-periplanar orientation ($180^\circ$ dihedral angle).In the provided molecule,the bromine atom is in an axial position (if we consider the chair conformation). However,the adjacent $\beta$-hydrogens are not anti-periplanar to the bromine atom due to the specific stereochemistry of the methyl groups.Specifically,the $C-H$ bonds at the $\beta$-carbons are not oriented anti to the $C-Br$ bond,preventing the necessary orbital overlap for the concerted $E2$ mechanism.

Why is the alkyl halide shown below not capable of undergoing an $E2$ reaction upon treatment with sodium ethoxide?

Similar Questions

Which of the following undergoes nucleophilic substitution reaction according to the $S_{N}1$ mechanism?

In $S_N1$ reaction, the alkyl halide that on hydrolysis produces a racemic mixture is

The major product obtained in the following reaction is $C_2H_5ONa + (CH_3)_3C-Cl \rightarrow$

Which one of the following is the Swartz reaction?

Nitrochloroform (Chloropicrin) is prepared by the action of chloroform and:

Vedclass Test Series

Exam Paper Generator

Online Exam Module