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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
CH₂=CHCH₂CH₃ (but-1-ene) has one double bond (degree = 1). Its chain isomer, 2-methylpropene (CH₃C(CH₃)=CH₂), has a similar boiling point, but cyclic isomers like cyclobutane can be separated by simple distillation due to a larger boiling point difference.
Ref: NCERT Class 11 Chemistry > Chapter 8: Organic Chemistry - Some Basic Principles and Techniques > Topic: Isomerism - Structural Isomerism - Chain Position Functional Metamerism
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