Chapter 10: Q.16. (page 401)

Question: Use the Hammond postulate to explain why ${(C H_{3})}_{2} C = C H_{2}$ reacts faster than $C H_{3} C H = C H_{2}$ in electrophilic addition of HX.

Short Answer

Expert verified

Answer

${(C H_{3})}_{2} C = C H_{2}$ generates a $3 °$ carbocation and imparts greater stability. Hence, ${(C H_{3})}_{2} C = C H_{2}$ reacts faster.

Step by step solution

Hammond postulate

The HX is added to that carbon in the $C = C$ bond of the alkene which is less substituted.

Reaction rates

The more substituted and stable carbocation leads to a faster reaction.

Products of the given reactions

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Question: Use the Hammond postulate to explain why ${(C H_{3})}_{2} C = C H_{2}$ reacts faster than $C H_{3} C H = C H_{2}$ in electrophilic addition of HX.

Short Answer

Step by step solution

Hammond postulate

Reaction rates

Products of the given reactions

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Question: Use the Hammond postulate to explain why (CH3)2C=CH2reacts faster than CH3CH=CH2 in electrophilic addition of HX.

Short Answer

Step by step solution

Hammond postulate

Reaction rates

Products of the given reactions

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Question: Use the Hammond postulate to explain why ${(C H_{3})}_{2} C = C H_{2}$ reacts faster than $C H_{3} C H = C H_{2}$ in electrophilic addition of HX.