1. Aqueous Basicity Order: "2-1-3, Not 3-2-1 in Water"

• Gas phase: 3 > 2 > 1 > $NH_{3}$ (remember: "3-2-1 Blast Off!" like a rocket countdown)
• Aqueous: 2 > 1 > 3 > $NH_{3}$ (remember: "Water Flips the 3" — solvation brings 3° down)

2. Sandmeyer vs Gattermann vs Schiemann: "S-G-S"

• Sandmeyer = Salt of copper (CuX, e.g., CuCl, CuBr, CuCN)
• Gattermann = Ground copper (Cu powder, metallic)
• Schiemann = Special fluorine route ($HBF_{4}$, the ONLY ArF method)

3. Gabriel Synthesis — "PAPA": Phthalimide Always Produces Primary Aliphatic

• Gabriel gives Primary Aliphatic Products Alone
• Cannot make Aromatic ($ArNH_{2}$), Secondary, or Tertiary amines

4. Hoffmann Bromamide — "H = –1 Carbon"

• Hoffmann = one carbon Hits the floor ($CO_{2}$ equivalent lost as $Na_{2}CO_{3}$)
• $RCONH_{2}$ (n carbons) → $RNH_{2}$ (n–1 carbons)

5. Carbylamine Test — "C for 1° Carbon-smelling"

• Carbylamine = Characteristic test for Class 1° (primary) amines
• Product is isocyanide (R–NC) which has a foul/unpleasant smell
• 2° and 3° = No smell = No test

6. Azo Coupling Medium: "PhOH = ALK, $PhNH_{2}$ = ACID"

• Ph-OH couples in ALKaline (phenoxide = activated nucleophile)
• Ph-$NH_{2}$ couples in ACID (weakly acidic keeps –$NH_{2}$ free; too acidic → protonates N, deactivates)

7. Hinsberg Test: "1° Soluble, 2° Insoluble, 3° No Reaction"

• Story: "1° sulfonamide is Social (soluble in NaOH); 2° sulfonamide is Stubborn (insoluble); 3° simply Stays away (no reaction)"