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Answer: Draw the substitution products for each of the

Chapter 9, Problem 45P

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QUESTION:

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. (R)-2-bromopentane + \(\mathrm{CH}_{3} \mathrm{O}^{-}\)            

b. (R)-3-bromo-3-methylheptane + \(\mathrm{CH}_{3} \mathrm{OH}\)

c. benzyl chloride + \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

d. allyl chloride + \(\mathrm{CH}_{3} \mathrm{OH}\)

e. 1-bromo-2-butene + \(\mathrm{CH}_{3} \mathrm{O}^{-}\)

f. 1-bromo-2-butene + \(\mathrm{CH}_{3} \mathrm{OH}\)

Questions & Answers

QUESTION:

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. (R)-2-bromopentane + \(\mathrm{CH}_{3} \mathrm{O}^{-}\)            

b. (R)-3-bromo-3-methylheptane + \(\mathrm{CH}_{3} \mathrm{OH}\)

c. benzyl chloride + \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

d. allyl chloride + \(\mathrm{CH}_{3} \mathrm{OH}\)

e. 1-bromo-2-butene + \(\mathrm{CH}_{3} \mathrm{O}^{-}\)

f. 1-bromo-2-butene + \(\mathrm{CH}_{3} \mathrm{OH}\)

ANSWER:

Solution 45P

Step 1 of 6

(a)

Treatment of (R)-2-bromopentane with methoxide ion gives (S)-2-methoxypentane. This reaction occurs through  mechanism, so the inversion of configuration takes place in the product.

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