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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: Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.

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

Question: What product is formed when each alkene is treated with HCl?

Question: How many degrees of unsaturation are present in each compound?

  1. C6H6
  2. role="math" localid="1648637368534" C8H18
  3. C7H8O
  4. C7H11Br
  5. C5H9N

Question: Draw a stepwise mechanism for the following reaction. This reaction combines two processes together: the opening of an epoxide ring with a nucleophile and the addition of an electrophile to a carbon–carbon double bond. (Hint: Begin the mechanism by protonating the epoxide ring.)
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