Chapter 10: Q8P-a (page 298)
How would you prepare the following alkyl halides from the corresponding alcohols?

Short Answer
The given compound is 2-chloro,2-methylpropane. It can be prepared as the following way:

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Chapter 10: Q8P-a (page 298)
How would you prepare the following alkyl halides from the corresponding alcohols?

The given compound is 2-chloro,2-methylpropane. It can be prepared as the following way:

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What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

Taking the relative reactivities of 1°, 2°, and 3° hydrogen atoms into account, what product(s) would you expect to obtain from monochlorination of 2-methylbutane? What would the approximate percentage of each product be? (Don’t forget to take into account the number of each kind of hydrogen.)
Draw structures corresponding to the following IUPAC names: (b) 3,3-Dichloro-2-methylhexane.
A chemist requires a large amount of 1-bromo-2-pentene as starting material for synthesis and decides to carry out an NBS allylic bromination reaction. What is wrong with the following synthesis plan? What side products would form in addition to the desired product?

Draw structures corresponding to the following IUPAC names: (e) 4-sec-Butyl-2-chlorononane.
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