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Ethanol is heated with concentrated H2SO4 at 140 degrees C to give an organic product X. X is then treated with HI. Identify the final products.

1. EtOH + EtI
2. EtI only
3. H2C=CH2
4. EtOH only

Correct answer: EtOH + EtI

Solution

H2SO4 at 140 deg C catalyses dehydration of 2 EtOH to diethyl ether (Et-O-Et). With one equivalent of HI, the ether undergoes nucleophilic cleavage: Et-O-Et + HI -> EtI + EtOH. With excess HI, both C-O bonds cleave giving 2 EtI. Under typical conditions with limited HI, products are EtOH and EtI.

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