This is a question from my 11th grade textbook, why does the alkylation of benzene with 1-chloropropane gives 2-propyl benzene and not 1-propylbenzene?

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This is a question from my 11th grade textbook, why does the alkylation of benzene with 1-chloropropane gives 2-propyl benzene and not 1-propylbenzene?

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Answer 1 · 2017-10-02T19:17:13

This I think is an example of Friedel Craft alkylation......

Explanation:

And this usually occurs in the presence of a strong Lewis acid such as $A l C l_{3}$ $AlCl_3$ .

i.e. $H_{3} C - C H_{2} C H_{2} C l + A l C l_{3} \to H_{3} C - C H_{2} C H_{2}^{+} + A l C l_{4}^{-}$ $H_3C-CH_2CH_2Cl + AlCl_3 rarr H_3C-CH_2CH_2^+ + AlCl_4^(-)$

And, formally, we gots a primary carbocation....

$H_{3} C - C H_{2} C H_{2}^{+}$ $H_3C-CH_2CH_2^+$ WHICH MAY undergo sigmatropic reaction to give the more stable secondary carbocation....i.e.

$H_{3} C - C H_{2} C H_{2}^{+} \to H_{3} C - + C H C H_{3}$ $H_3C-CH_2CH_2^+ rarr H_3C-stackrel(+)CHCH_3$

And the $2^{\circ}$ $2^@$ carbocation may be the reactive intermediate in the alkylation.

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This is a question from my 11th grade textbook, why does the alkylation of benzene with 1-chloropropane gives 2-propyl benzene and not 1-propylbenzene?

1 Answer

Explanation:

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