A student is asked to react 3-methyl-2-butanol with HBr. Predict the products an

Question

A student is asked to react 3-methyl-2-butanol with HBr. Predict the products and explain why the experiment will not be as successful for production of an alkyl bromide as the reaction of 1-butanol with HBr. Ch8.2 Critical Thinking #10

Explanation / Answer

CH3-CH(OH)-CH(CH3)-CH3 + HBr ----> CH3-CH(Br)-CH(CH3)-CH3 + CH3-C=C(CH3)-CH3 as seen above along with alkyl bromide alkenes may be formed. This due to elimination reaction which occurs along substitution reactions. Such kinds of reactions occur simultaneously for secondary and tertiary alcohols but not for primary alcohols. Hence 1butanol which is primary alcohol yields more alkyl bromide

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