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Consider the structures of 1-hexanol and cyclohexanol. In the presence of acid and heat, choose which will undergo a more effective dehydration reaction because it is a choose... alcohol and the choose... in the intermediate of the mechanism will be more stable.

A) 1-hexanol, primary, carbocation
B) Cyclohexanol, secondary, carbocation
C) 1-hexanol, secondary, carbocation
D) Cyclohexanol, primary, carbocation

1 Answer

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Final answer:

Cyclohexanol will undergo a more effective dehydration reaction compared to 1-hexanol because it is a secondary alcohol, and the secondary carbocation intermediate formed is more stable than a primary carbocation. Therefore, the correct answer to this question is: B) Cyclohexanol, secondary, carbocation.

Step-by-step explanation:

The student's question revolves around which alcohol, 1-hexanol or cyclohexanol, would undergo a more effective dehydration reaction in the presence of acid and heat. Dehydration of alcohols typically involves the removal of an OH group and a hydrogen atom from adjacent carbon atoms, resulting in the formation of an alkene and water. The stability of the carbocation intermediate is crucial for the reaction's effectiveness.

1-Hexanol is a primary alcohol; When it undergoes dehydration, it forms a primary carbocation, which is less stable than secondary or tertiary carbocations. Cyclohexanol, on the other hand, is a secondary alcohol. Secondary alcohols, when dehydrated, form secondary carbocations that are more stable than primary carbocations due to additional alkyl groups providing electron donation through hyperconjugation.

Cyclohexanol can undergo a more effective dehydration reaction because it is a secondary alcohol and the secondary carbocation formed in the intermediate of the mechanism will be more stable compared to a primary carbocation that would be formed from 1-hexanol.

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