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Question

Acetophenone on chlorination with Cl2 and FeCl3 gives major product as:

A
o-chloroacetophenone
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B
p-chloroacetophenone
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C
m-chloroacetophenone
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D
(a) and (b) above.
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Solution

The correct option is C m-chloroacetophenone
Acetophenone react with halogens in the presence of a lewis acid like anhydrous FeCl3,FeBr3 or AlCl3 to yield m-chloroacetophenone.
COCH3 is the meta directing group because it is electron withdrawing group. It pulls the electron density towards itself and acts as a deactivating group on ring which gives generally meta substituents as a major product. Thus option (c) is correct.

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