Which of the alcohols listed below would you expect to react most rapidly with HBr, assuming the reaction pathway is predominantly Sn1? a) CH3CH2CH2CH2CH2OH b) (CH3)2CH2CH2OH c) (C... Which of the alcohols listed below would you expect to react most rapidly with HBr, assuming the reaction pathway is predominantly Sn1? a) CH3CH2CH2CH2CH2OH b) (CH3)2CH2CH2OH c) (CH3)2CHCHOH3 d) CH3CH2CH2CH2OH e) (CH3)2C(CH3)OH Read more

Understand the Problem

The question is asking which alcohol from the provided list would react most rapidly with HBr, under the assumption that the reaction follows an Sn1 pathway. To answer this, we will consider the structure of the alcohols and their stability as carbocations, as Sn1 reactions favor more stable intermediates.

More Information

Tertiary alcohols react more rapidly with HBr in an SN1 mechanism due to the formation of a stable tertiary carbocation.

Tips

Avoid assuming that all alcohols react at the same rate; tertiary carbocations are more stable.

Sources

• Solved Which of the alcohols listed below would you expect - Chegg - chegg.com
• B 15. Which of the alcohols listed below would you expect to react ... - numerade.com