Aromatics, Acylation, And Bromination

Chemistry Level 2

$\ce{Benzene}$ is reacted with $\ce{propandioyl~dichloride}$ in the presence of $\ce{aluminium~chloride}$ , and this is followed by an addition of $\ce{Br} _2$ to the reaction.

Pick the major product from choices $A$ , $B$ , or $C$ .

David's Organic Chemistry Set

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A

B

C

1 solution

David Hontz
Jul 14, 2016

First, Friedel Craft Acylation occurs to form a bicyclic compound
$Br_2$ is incapable, by itself, of brominating the aromatic ring; however, the carbon alpha to both ketones has highly acidic hydrogens. $Br_2$ will react with one of these acidic hydrogens, forming $HBr$ and brominating the carbon with the second $Br$

$Answer = \boxed{C}$

Aromatics, Acylation, And Bromination

David's Organic Chemistry Set

David's Physical Chemistry Set

1 solution

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