Q.Write the mechanism of acid dehydration of ethanol to yield ethene.
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Start your 14-day free trial to unlock the full solution →Ethanol's acid-catalysed dehydration to ethene (with conc. H2SO4 at ~443 K) proceeds via protonation, loss of water to a carbocation, then loss of a beta-H — an E1 mechanism.
Step 1 — Protonation of the hydroxyl group:
CH3–CH2–OH + H+ → CH3–CH2–O+H2
(conc. H2SO4 protonates the oxygen, converting the poor leaving group –OH into the good leaving group –OH2+)
Step 2 — Loss of water (rate-determining step):
CH3–CH2–O+H2 → CH3–CH2+ (a primary carbocation) + H2O
Step 3 — Loss of a beta-hydrogen (elimination):
A base (HSO4⁻, or another ethanol molecule) removes a proton from the beta-carbon (the CH3 group) adjacent to the carbocation, and the electron pair forms the new pi bond: …
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