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Solved: Indicate which of the compounds in each pair will
Chapter 10, Problem 44P(choose chapter or problem)
Indicate which of the compounds in each pair will give a higher substitution-product to elimination product ratio when it reacts with isopropyl bromide:
a. ethoxide ion or tert-butoxide ion
b. \(^{-}OCN\) or \(^{-}SCN\)
c. \(Cl^{-}\) or \(Br^{-}\)
d. \(CH_{3}S^{-}\) or \(CH_{3}O^{-}\)
Questions & Answers
QUESTION:
Indicate which of the compounds in each pair will give a higher substitution-product to elimination product ratio when it reacts with isopropyl bromide:
a. ethoxide ion or tert-butoxide ion
b. \(^{-}OCN\) or \(^{-}SCN\)
c. \(Cl^{-}\) or \(Br^{-}\)
d. \(CH_{3}S^{-}\) or \(CH_{3}O^{-}\)
ANSWER:Solution 44P
Step 1 of 4
(a)
Sterically hindered nucleophiles have a tough time to attack from the back side of α-carbon, and thus elimination reaction is possible instead of substitution.
So, the reaction of ethoxide ion with isopropyl bromide gives the substitution product.
The reaction of tert-butoxide ion with isopropyl bromide gives the elimination product propene. Thus, the reaction is as follows:
