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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: (a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.

Question: Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China.

(a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid.

(b) Draw the structure of a stereoisomer that has a lower melting point.

Question: Draw the products formed when each alkene is treated with BH3followed by H2O2,HO-. Include the stereochemistry at all stereogenic centers.

Question: Use the Hammond postulate to explain why (CH3)2C=CH2reacts faster than CH3CH=CH2 in electrophilic addition of HX.

Question: When buta-1,3-diene (CH2=CH-CH=CH2) is treated with HBr, two constitutional isomers are formed CH3CHBr-CH=CH2and Br-CH2CH=CHCH2. Draw a stepwise mechanism that accounts for the formation of both products.
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