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Butanal (CH₃CH₂CH₂CHO) reacts with NH₂OH to form an oxime (CH₃CH₂CH₂CH\=NOH), but the carbonyl carbon becomes chiral in the intermediate, yielding a racemic mixture.
Ref: NCERT Class 12 Chemistry > Chapter 12: Aldehydes, Ketones and Carboxylic Acids > Topic: Reactions due to α-Hydrogen - Aldol, Cannizzaro and Acidity of Carboxylic Acids
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