Question

In: Chemistry

Draw the major alkene product formed from dehydrating the following alcohols? a) 2-methylcyclohexanol b) 2,3-dimethylcyclohexanol c)...

Draw the major alkene product formed from dehydrating the following alcohols?

a) 2-methylcyclohexanol

b) 2,3-dimethylcyclohexanol

c) 1,2,2-trimethylcyclohexanol

d) 2,2-dimethylcyclohexanol (hint: consider carbocation shifts)    

e) 1,2-cyclohexanediol (hint: consider keto-enol tautomerism)

Solutions

Expert Solution

?Alcohols when heated with strong acids undergo 1,2-elimination reaction to form (dehydration product) alkene and water. Alcohols undergo elimination by E1 or E2 elimination mechanism. Primary alcohols form alkene generally by E1 while secondary and tertiary by E2 mechnism. Reactivity order of alcohols is as tertiary>secondary>primary. Marjor product is always more substituted alkene (Regioselectivity:Zaitsev's Rule)

queen_honey_blossom answered 12 hours ago
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