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Chapter 10: PROBLEM 10.50 (page 422)

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?

Short Answer

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Answer

Step by step solution

01

Addition of HCl to the alkene

The addition of HCl to the alkene occurs in a way that Cl goes to the stable carbocation (more substituted carbon) and H goes to the less substituted carbon.

02

Stereoisomers

Stereoisomers give the location of the substituents in the three-dimensional framework. They include both geometrical and optical isomers.

03

Explanation

3-Chloro-3-methylhexane is shown below:

CH3-CH2-CH2-C(Cl)(CH3)-CH2-CH3

The three isomers of the alkene that can give3-chloro-3-methylhexane are shown below:

Isomers of alkene

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Most popular questions from this chapter

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 the isomers for the following compounds and then name each one:

a. 2-methyl-2,4-hexadiene

b. 2,4-heptadiene

c. 1,3-pentadiene

Question: Devise a synthesis of each compound from the indicated starting material.

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

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.
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