In solvolysis of 1,2-dimethylpropyl p-toluene | vedclass

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Question

(D) The solvolysis of $1,2$-dimethylpropyl $p$-toluenesulfonate in acetic acid proceeds via an $S_N1$ mechanism involving the formation of a carbocati

Vedclass · Accepted Answer

$5$

Vedclass · Answer

(D) The solvolysis of $1,2$-dimethylpropyl $p$-toluenesulfonate in acetic acid proceeds via an $S_N1$ mechanism involving the formation of a carbocation intermediate.$1$. The initial carbocation formed is a secondary carbocation: $(CH_3)_2CH-CH^+-CH_3$.$2$. This secondary carbocation can undergo elimination to form two alkenes: $2,3$-dimethylbut-$2$-ene and $2,3$-dimethylbut-$1$-ene.$3$. The secondary carbocation can also undergo substitution with acetic acid to form $1,2$-dimethylpropyl acetate (as a racemic mixture of $d$ and $l$ isomers).$4$. Additionally,the secondary carbocation can undergo a $1,2$-hydride shift to form a more stable tertiary carbocation: $(CH_3)_2C^+-CH_2CH_3$.$5$. This tertiary carbocation undergoes substitution with acetic acid to form $2$-methylbutan-$2$-yl acetate.$6$. Total products = $2$ (alkenes) + $2$ (substitution from secondary carbocation) + $1$ (substitution from tertiary carbocation) = $5$ products.

In solvolysis of $1,2$-dimethylpropyl $p$-toluenesulfonate in acetic acid at $75\,^oC$,how many (alkene + substitution) products will be formed?

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