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Chemistry20251.5 marksShort answerHaloalkanes and Haloarenes

Answer the following.

Which will react faster by S_N2 mechanism with –OH, and why: (CH₃)₃CCl or CH₃Cl?

Which will react faster by $S_N2$ mechanism with –OH, and why: $(\text{CH}_3)_3\text{CCl}$ or $\text{CH}_3\text{Cl}$?

Answer

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Official answer key
$\mathrm{CH_3Cl}$, lacks bulky substituents on the carbon atom that bears the leaving group. As a result, in the $S_N2$ reaction with $\mathrm{OH^-}$, $\mathrm{CH_3Cl}$ has a faster reactivity than $(\mathrm{CH_3})_3\mathrm{CCl}$.