Depending on wether I consider the stability of the substrate (more substituted

Question

Depending on wether I consider the stability of the substrate (more substituted double bond is more stable and less reactive and therefore slowest) or the stability of the carbocation ( more substituted double bond gives less stable carbocation and therefore slowest reaction--in addition to the Hammond postulate which states that the if the carbocation is less stable than the reactants, the closer the transition state is to the carbocation) the answer is either A or E respectively. Which is the correct answer?

Which of the following alkenes will react with HBr at the slowest rate?

1-heptene

cis-2-heptene

trans-2-heptene

2-methyl-hex-2-ene

2,3-dimethyl-pent-2-ene

1-heptene

cis-2-heptene

trans-2-heptene

2-methyl-hex-2-ene

2,3-dimethyl-pent-2-ene

Explanation / Answer

Answer is 1-heptene, which proceeds via less stable carbocation (Hammond postulate)

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