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Question
Give reasons for the following:
(CH3)3C–O–CH3 on reaction with HI gives (CH3)3C–I and CH3–OH as the main products and not (CH3)3C–OH and CH3–I.
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Solution 1
Usually, iodide, being a big nucleophile, attacks on the group with low steric hindrance and the reaction proceeds by SN2 mechanism.
However, in this case, methanol, on leaving generates a tertiary carbocation, which is more stable. Hence, this reaction proceeds by SN1 mechanism and therefore, we get (CH3)3C-I and CH3-OH as the major products.
Solution 2
CH3)3-C–O–CH3 is an ether with two different alkyl groups, of which (CH3)3-C-, a tertiary alkyl group, on reaction with hydrogen halide (HI) forms a tertiary halide. This occurs as the reaction is an SN1 reaction. The reaction involves the formation of a stable carbocation. If the ether has a primary alkyl group, then the reaction follows the SN2 mechanism.
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