Question

H8.21 Level 2 Which of the following alkyl halides would undergo a solvolysis reaction most readily?...

H8.21 Level 2
Which of the following alkyl halides would undergo a solvolysis reaction most readily?

A. 2-chloro-4-methylhexane
B. 1-chloro-2-methylhexane
C. 2-chloro-2-methylhexane
D. 2-chloro-3-methylhexane

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Answer #1

It is a type of nucleophilic substitution (SN1) / (SN2) where solvent acts as nucleophile. Solvolysis involving water is called hydrolysis, involving alcohal is alcoholysis and involving ammonia is ammonolysis.

All the alkyl halides have chlorine as leaving group.

Thus, the molecule which will form stable carbocation will undergo solvolysis rapidly.

In above compounds, only 2-chloro-2-methylhexane forms tertiary carbocation after the leaving group is removed so it will undergo solvolysis rapidly.

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