The reaction between 4-methyl-1-pentanol and HBr to yield 4-methyl-1-pentene is probably: A)an S_N1-type reaction involving the protonated alcohol as the substrate. B)an S_N2-type reaction involving the protonated alcohol as the substrate. C)an E1-type reaction involving the protonated alcohol as the substrate. D)an E2-type reaction involving the protonated alcohol as the substrate. E)an epoxidation reaction.

Question

Quizplus · Accepted Answer

The reaction between 4-methyl-1-pentanol and HBr involves an elimination reaction with protonated alcohol acting as the substrate. Since the reaction involves a primary alcohol, the mechanism is likely to be E2-type rather than E1-type (which is favored for tertiary substrates). Therefore, the best choice is D, an E2-type reaction involving the protonated alcohol as the substrate.

The Reaction Between 4-Methyl-1-Pentanol and HBr to Yield 4-Methyl-1-Pentene Is