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Chapter 17: Q17-61E (page 567)

Question:Reaction of (S)-3-methyl-2-pentanone with methyl magnesium bromide followed by acidification yields 2,3-dimethyl-2-pentanol. What is the stereochemistry of the product? Is the product optically active?

Short Answer

Expert verified

(S)-3-methyl-2-pentanone treated with methylmagnesium bromide in the presence of ether followed by the hydrolysis gives (S)-2,3-dimethyl-2-pentanol.

Here, the stereochemistry of the product does not change because the addition of Grignard reagent to the carbonyl compound does not produce a new chirality centre so there is no change at the chiral centre, which is already present. Hence, the product, which is formed, is an optically active compound.

Step by step solution

01

What is the stereochemistry of the product?

Treatment of (S)-3-methyl-2-pentanone with methylmagnesium bromide in the presence of ether followed by hydrolysis gives (S)-2,3-dimethyl-2-pentanol.

02

Is the product optically active?

Here, the stereochemistry of the product does not change because the addition of Grignard reagent to the carbonyl compound does not produce a new chirality centre so there is no change at the chiral centre, which is already present. Hence, the product, which is formed, is an optically active compound.

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