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Chapter 10: PROBLEM 10.62 (page 423)

Question: Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively.

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01

Regioselectivity

The regioselectivity term is used when a compound has many locations to form products. But the attacking reagent attacks a particular location and forms a regioselective product.

02

Explanation for A

When alkene A is treated with HBr, Br can attack at two places, but it prefers the carbon adjacent to the methoxy group as it is more electrophilic. As a result, it forms a regioselective product.

03

Explanation for B

When alkene B is treated with HBr, Br can attack at two places, but it prefers the carbon away from the carbonyl group as it is more electrophilic. As a result, it forms a regioselective product.

Regioselective product obtained from B

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Most popular questions from this chapter

Question: How many rings and π bonds does a compound with molecular formula C10H14 possess? List all possibilities.

Question: What alkylborane is formed from hydroboration of each alkene?

Question: a. Which diastereomer of oct-4-ene yields a mixture of two enantiomers, (4R,5R)- and (4S,5S)-4,5-dibromooctane on reaction with Br2 ?

b. Which diastereomer of oct-4-ene yields a single meso compound, (4R,5S)-4,5-dibromooctane?

Question: What alkylborane is formed from hydroboration of each alkene?

Question: Draw the products, including stereochemistry, of each reaction. 
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