Question

(R)-2-iodo-3-methylbutane is treated with sodium bromide in acetone. Select all products that are formed.

(R)-2-iodo-3-methylbutane is treated with sodium bromide in acetone. Select all products that are formed.



2-methylbut-2-ene


(R)-3-methyl-2-butanol


(S)-2-bromo-3-methylbutane


3-methylbut-1-ene


2-methylbutan-1-ol


2-methylbutan-2-ol


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Answer #1

Correct option:

(S)-3-methyl-2-butanol

3-methylbut-1-ene

2-methylbut-2-ene

Explanation:

NaOH + 2-methylbut-2-ene 3-methylbut-l-ene OH (R)-2-iodo-3-methylbutane (S)-3-methylbutan-2-ol

(S)-3-methyl-2-butanol is the result of SN2 reaction between (R)-2-iodo-3-methylbutane and hydroxide nucleophile. 3-Methylbut-1-ene and 2-methylbut-2-ene are the results of E2 elimination of (R)-2-iodo-3-methylbutane with hydroxide base.

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