See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Basicity Order of Nitrogen in LSD **Step 1: Identify the three nitrogen atoms** - **N(1)**: Secondary amine in indole ring (aromatic N-H) - **N(2)**: Tertiary amine in piperidine ring (aliphatic) - **N(3)**: Tertiary amine in amide group (C=O attached) **Step 2: Analyze basicity factors** Basicity depends on electron density and lone pair availability: - **N(2) (Highest basicity)**: Aliphatic tertiary amine with full electron density on nitrogen; lone pair is most available for protonation - **N(3) (Medium basicity)**: Tertiary amine but attached to carbonyl group. The $C=O$ is electron-withdrawing, reducing electron density on N through the acyl group. However, it's still an aliphatic tertiary amine - **N(1) (Lowest basicity)**: Secondary aromatic amine in indole. The lone pair is delocalized into the aromatic $\pi$ system, making it unavailable for protonation **Step 3: Establish the order** $$\boxed{N(2) > N(3) > N(1)}$$ **Answer: (C) $2>3>1$** The aliphatic tertiary amine is most basic, the acyl-substituted amine is intermediate, and the aromatic amine is least basic due to resonance stabilization.