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Write Brief Answer · Q47

Q.CH3-CH(CH3)-CH(OH)-CH3 →H+/heat\xrightarrow{H^+/heat} (A) major product →HBr\xrightarrow{HBr} (B) major product
Identify A and B

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Step 1. The starting alcohol, CH3-CH(CH3)-CH(OH)-CH3 (3-methylbutan-2-ol), is protonated by H+ and loses water (E1 dehydration) to give a SECONDARY carbocation at C2: CH3-CH(CH3)-CH+-CH3.

Step 2. This secondary carbocation sits directly next to a carbon (C3) that, if a hydride shifts across from it, would become a TERTIARY carbocation -- a 1,2-hydride shift from C3 to C2 does exactly this, converting the cation to the more stable tertiary carbocation CH3-CH2-C+(CH3)-CH3 (numbering the rearranged skeleton fresh, this is the 2-methylbutan-2-yl cation).

Step 3. Losing a proton (E1, Zaitsev's rule favouring the more substituted alkene) from this rearranged tertiary carbocation gives A = 2-methylbut-2-ene, CH3-CH=C(CH3)-CH3, the major dehydration product (rather than the 'naive', non-rearranged 3-methylbut-2-ene that a simple, no-rearrangement analysis might predict). …

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