JEE MainChemistryAmines
An organic compound A with molecular formula C ₅ H ₁₃ N is optically active. It reacts with benzenesulfonyl chloride to form a precipitate that does not dissolve in aqueous NaOH . Furthermore, it does not yield nitrogen gas when treated with nitrous acid. The structure of A is:
Options
- ACH ₃ NHCH ₂ CH ₂ CH ₂ CH ₃
- BCH ₃ CH ( NH ₂) CH ₂ CH ₂ CH ₃
- CCH ₃ NHCH ( CH ₃) CH ₂ CH ₃
- DCH ₃ CH ₂ NHCH ( CH ₃)₂
Correct answer
C. CH ₃ NHCH ( CH ₃) CH ₂ CH ₃
Step-by-step solution
The compound does not yield N ₂ gas with HNO ₂ and forms an alkali-insoluble product with benzenesulfonyl chloride (Hinsberg's reagent). This indicates that the compound is a secondary amine. The molecular formula is C ₅ H ₁₃ N . Since the compound is optically active, it must possess a chiral carbon atom. Let us examine the given options: First structure: CH ₃ NHCH ₂ CH ₂ CH ₂ CH ₃ is a secondary amine but is achiral. Second structure: CH ₃ CH ( NH ₂) CH ₂ CH ₂ CH ₃ is a primary amine. Third structure: CH ₃ NHCH (