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Solved: For each of the following reactions, draw the
Chapter 10, Problem 41P(choose chapter or problem)
For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.
a. (R)-2-bromohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
b. (R)-3-bromo-3-methylhexane + \(\mathrm{CH}_{3} \mathrm{OH}\)
c. trans-1-chloro-2-methylcyclohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
d. trans-1-chloro-3-methylcyclohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
e. 3-bromo-3-methylpentane + high concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\)
f. 3-bromo-3-methylpentane + \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)
Questions & Answers
QUESTION:
For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.
a. (R)-2-bromohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
b. (R)-3-bromo-3-methylhexane + \(\mathrm{CH}_{3} \mathrm{OH}\)
c. trans-1-chloro-2-methylcyclohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
d. trans-1-chloro-3-methylcyclohexane + high concentration of \(\mathrm{CH}_{3} \mathrm{O}^{-}\)
e. 3-bromo-3-methylpentane + high concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\)
f. 3-bromo-3-methylpentane + \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)
ANSWER:Solution 41P
Step 1 of 6
(a)
Methoxide ion is a strong base, which favors reaction. Here two types of -hydrogens are present and there is a chance of formation of two products, 1-hexene and 2-hexene. But only one product 2-hexene is formed due to its participation in conjugation. According to Saytzeff’s rule highly substituted alkenes are more stable than less substituted alkenes.
