TA: HSIEN-PO CHIU Oct 30 & Nov 1, 2007 Exp 21 . Dehydration of 4-methylcyclohexanol Principle : 1. Zaitsev’s rule: When HZ is removed from a species to form an alkene, hydrogen is lost preferentially from the carbon atom that has fewer hydrogens. ‘The rich get richer and the poor get poorer.’ KOH CH 3 CH 2 CHICH 3 CH 3 CH=CHCH 3 2. Anti-periplanar geometry of E2 mechanism I I CH 3 H H H 3 C H + I CH 3 H H H H 3 C OH-3. Rearrangement of carbocation (hydride shift) of E1 mechanism OH H + O H H- H 2 O 1 o H hydride shift 3 o H- H + 4. Acid-catalyzed dehydration of 4-methylcyclohexanol (E1 mechanism) OH H + O H H H- H + Procedure : see page 104. Apparatus setup : see page 314-315.
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