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Q.Write the reaction mechanism when propan-1-ol is treated with Conc. H₂SO₄ at 443 K.

Mizoram MbseMizoram Board of School Education HSSLC 2025Subjective· 2mImportance★★★★★
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This is acid-catalysed dehydration: the alcohol is protonated, water leaves, and a β-hydrogen is removed to form the C=C double bond of propene.

When propan-1-ol (CH₃-CH₂-CH₂-OH) is heated with conc. H₂SO₄ at 443 K, it undergoes acid-catalysed dehydration (E1-type elimination) to give propene.

Step 1 — Protonation of the alcohol:

The oxygen lone pair of the -OH group attacks a proton donated by H₂SO₄, converting the poor leaving group -OH into the good leaving group -OH₂⁺:

CH3−CH2−CH2−OH+H+→CH3−CH2−CH2−OH2+CH_3-CH_2-CH_2-OH + H^+ \rightarrow CH_3-CH_2-CH_2-OH_2^+

Step 2 — Formation of the carbocation (loss of water):

The C–O bond breaks heterolytically and a molecule of water leaves, generating a carbocation. (Since a primary carbocation is very unstable, in practice this step and the next proceed in a concerted, E2-like fashion for primary alcohols, but the overall bond-breaking sequence is the same.)

CH3−CH2−CH2−OH2+→CH3−CH2−CH2++H2OCH_3-CH_2-CH_2-OH_2^+ \rightarrow CH_3-CH_2-CH_2^+ + H_2O

Step 3 — Elimination of a β-hydrogen: …

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