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Chapter 15: Q52. (page 570)

Question: (a) Draw the products (including stereoisomers) formed when 2-methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4-dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.

Short Answer

Expert verified

Answer

(a)

(b)

Step by step solution

01

Anti-Markovnikov Rule

The anti-Markovnikov rule states that the addition of hydrogen bromide in the presence of peroxide to an alkene would substitute the hydrogen atom at the more substituted carbon of the alkene group.

02

Products

(a) 2-methylhex-2-ene reacts with HBr in the presence of peroxide to form a set of products, including a pair of stereoisomer, as given below:


Formation of bromo-substituted hexanes

(b) (S)-2,4-Dimethylhex-2-ene reacts with HBr in the presence of peroxide to form a set of products, including a pair of stereoisomers, as given below:

Formation of products

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Most popular questions from this chapter

Question: As described in Section 9.16, the leukotrienes, important components in the asthmatic response, are synthesized from arachidonic acid via the hydroperoxide 5-HPETE. Write a stepwise mechanism for the conversion of arachidonic acid to 5-HPETE with O2 .

Question: Draw the products of radical chlorination and bromination of each compound. For which compounds is a single constitutional isomer formed for both reactions? What must be true about the structure of a reactant for both reactions to form a single product?

Question: a. What product(s) (excluding stereoisomers) are formed when Y is heated with Cl2 ?

b. What product(s) (excluding stereoisomers) are formed when Y is heated with Br2?

c. What steps are needed to convert Y to the alkene Z?

Question. Devise a synthesis of hexane-2,3-diol from propane as the only source of carbon atoms. You may use any other required organic or inorganic reagents.

Consider the following Bromination:

(a) Calculate ฮ”Hยฐ for this reaction by using the bond dissociation energies in Table 6.2.

(b) Draw out a stepwise mechanism for the reaction, including the initiation, propagation, and termination steps.

(c) Calculate ฮ”Hยฐ for each propagation step.

(d) Draw an energy diagram for the propagation steps.

(e) Draw the structure of the transition state of each propagation step
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