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Properties of Ethers Questions in English

Class 12 Chemistry · Alcohols, Phenols and Ethers · Properties of Ethers

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MediumMCQ
Which among the following does $NOT$ undergo Williamson's synthesis?
A
$C_2H_5Br$
B
$CH_3-CH(CH_3)-CH_2Br$
C
$C_6H_5Br$
D
$C_6H_5-CH_2Br$

Solution

(C) Williamson's synthesis involves an $S_N2$ reaction between an alkyl halide and an alkoxide ion.
For the reaction to proceed, the alkyl halide must be primary $(1^\circ)$ or secondary $(2^\circ)$ to minimize steric hindrance.
$C_6H_5Br$ (bromobenzene) does not undergo $S_N2$ reactions because the $C-Br$ bond has partial double-bond character due to resonance, and the $sp^2$ hybridized carbon atom is sterically hindered.
Therefore, $C_6H_5Br$ does not undergo Williamson's synthesis.

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