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In which of the following reactions, the product obtained is chiral?

1. \( C H_{3} C O C H_{3} \stackrel{N a B H_{4}}{\longrightarrow} \)
2. \( C H_{3} \) COCl Rosenmund's reduction
3. \( C H_{3} C H_{2} C O_{2} C H_{2} C H_{3} \stackrel{S n, H C l}{\longrightarrow} \)
4. \( C H_{3} C H_{2} C O C H_{3} \stackrel{L i A H H_{4}}{\longrightarrow} \)

Correct answer: \( C H_{3} C H_{2} C O C H_{3} \stackrel{L i A H H_{4}}{\longrightarrow} \)

Solution

LiAlH4 reduces 2-butanone to 2-butanol, and the carbon bearing OH is attached to CH3, C2H5, H, and OH, so it is chiral. The other options give products with symmetry or no stereocenter.

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