The ether shown reacts with cold $HI$ . Because one alkyl group can form a stable carbocation, the cleavage goes by the $S_{N} 1$ route. Which structure is the alkyl iodide formed?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The ether is tert-butyl ethyl ether. The protonated ether easily ionises to the tert-butyl cation and ethanol, since the cation is tertiary. Iodide captures it to give 2-iodo-2-methylpropane; the ethyl carbon is not attacked, so iodoethane is not the main product.

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The ether shown reacts with cold HI. Because one alkyl group can form a stable carbocation, the cleavage goes by the SN​1 route. Which structure is the alkyl iodide formed?

Answer: C

More questions on Williamson synthesis and HI cleavage of drawn ethers

The ether shown reacts with cold $HI$ . Because one alkyl group can form a stable carbocation, the cleavage goes by the $S_{N} 1$ route. Which structure is the alkyl iodide formed?