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Chapter 10: PROBLEM 10.53 (page 422)

Question: Which alkene reacts faster with HBr? Explain your choice

Short Answer

Expert verified

Answer

B

Step by step solution

01

Reactivity of alkene  

The reactivity of an alkene depends on resonance stabilization. If the alkene forms a resonance stabilized carbocation on reaction with HBr, it will react faster.

02

Explanation

Compound B reacts with HBr to give the benzyl carbocation on either side of the double bond. The benzyl carbocation is the most stable because it undergoes resonance.

Therefore, compound B reacts faster than A.

Resonance stabilization of B

Compound A reacts with HBr does not give more stable carbocation. Therefore, there is no resonance stabilization and compound A reacts slow.

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Most popular questions from this chapter

Question: Explain why A is a stable compound but B is not.

Question: Give the IUPAC name for each compound.

a.

b.

c.

d.

e.

f.

Question: Draw the products of each reaction and indicate their stereochemistry.

Question: What alkene can be used to prepare each alkyl halide or dihalide as the exclusive or major product of an addition reaction?

a.

b.

c.

d.

Question: Draw a stepwise mechanism for the following reaction.
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