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Reactions of Aryl Amines (Diazo Salts)

What product ...

Question

What product would be formed from the reaction of (R)-2-bromooctane and hydroxide ion in dimethylformamide (DMF) at room temperature?
(correct answer +1, wrong answer -0.25)

A

Octanol

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B

(S)-2-octanol

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C

(R)-2-octanol

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D

Racemic mixture of 2-octanol

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Solution

The correct option is B (S)-2-octanol
Above reaction follows $S_{N} 2$ mechanism in which inversion of the stereochemistry takes place. Hence, absolute configuration (R) would change into (S) in product and 2-octanol would be formed.

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