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MCAT Organic Question — Alkyl Halide

Which alcohol will most easily react with HCl to form an alkyl halide?


a) 1° alcohol

b) 2° alcohol

c) 3° alcohol

d) all alcohols react equally to form alkyl halides



In terms of reactivity, 3° alcohols > 2° alcohols > 1° alcohols in reactions with HCl forming alkyl halides. For 3° alcohols, the reaction proceeds by an SN1 mechanism. For small 1° and 2° alcohols, there is some reactivity by an SN2 mechanism, but the SN1 mechanism with tertiary alcohols is the most reactive.

a) 1° alcohol, incorrect.

b) 2° alcohol, incorrect.

c) 3° alcohol, correct.

d) all alcohols react equally to form alkyl halides, incorrect.

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