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vovangra [49]
3 years ago
11

4. When benzene reacts with 1-chloro-2,2-dimethylpropane (neopentyl chloride) in the presence of aluminum chloride, the major pr

oduct is 2-methyl-2-phenylbutane, not 2,2-dimethyl-1- phenylpropane (neopentylbenzene). Explain this result

Chemistry
1 answer:
BARSIC [14]3 years ago
8 0

Answer:

Explanation:

In this case, we have a <u>Friedel-Craft reaction</u> (see figure 1). Usually in this type of reaction, the benzene ring is <u>bonded directly to the carbon that has the halide atom</u>. But in this specific case, this is not happening.

To understand why we have to remember the reaction mechanism of this reaction. As first, step the Cl-C bond attacks the AlCl_3 and we form a new bond between the alkyl halide and the AlCl_3, finally the C-Cl bond is broken and a <u>carbocation is formed</u>. In this case, we will have a primary carbocation, a very <u>unstable species</u>. Therefore we will have a <u>methyl shift</u> to obtain a tertiary carbocation.

This tertiary carbocation will react with and continues the reaction. (See figure 2)

I hope it helps!

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