Alkylation / Bromination of Benzene

Chemistry Level 2

$\ce{Benzene}$ is reacted first with $\ce{propyl~chloride}$ in $\ce{AlCl}_3$ , followed by a reaction of the addition of $\ce{N-bromosuccinimide}$ in $\ce{light}$ .

Choose the major product from among choices $A$ through $C$ .

David's Organic Chemistry Set

David's Physical Chemistry Set

C

B

A

1 solution

David Hontz
Jul 16, 2016

The first step is an Alkylation reaction. A $1^{\circ}$ cation forms from the removal of $Cl$ ; and a rearrangement occurs to form a more stable $2^{\circ}$ carbocation. This causes benzene to be alkylated to $\ce{isopropyl~benzene}$ . This now disqualifies choice $A$ from being correct

Next, $\ce{NBS}$ will add a $Br$ allylic to the benzene ring, forming $\ce{2-bromo-2-phenyl~propane}$ . This disqualifies choice $B$ from being correct $Answer = \boxed{C}$

Alkylation / Bromination of Benzene

1 solution

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