Named Reactions

1. HVZ (Hell-Volhard-Zelinsky): $\text{RCOOH} + X_2 \xrightarrow{\text{Red P}} \text{RCHXCOOh}$

• Reagents: X2 (Cl2, Br2) + Red phosphorus
• Product: alpha-halocarboxylic acid
• Requires: alpha-H present

2. Fischer Esterification: $\text{RCOOH} + \text{R'OH} \underset{\Delta}{\overset{\text{conc. H}_2\text{SO}_4}{\rightleftharpoons}} \text{RCOOR'} + \text{H}_2\text{O}$

• Reversible, acid-catalyzed
• Equilibrium: K ≈ 1 for simple substrates

3. Decarboxylation (Soda Lime): $\text{RCOONa} + \text{NaOH} \xrightarrow{\text{CaO, heat}} \text{R-H} + \text{Na}_2\text{CO}_3$

• Soda lime = NaOH + CaO
• Product: alkane with (n–1) carbons

4. Acyl Chloride via SOCl2: $\text{RCOOH} + \text{SOCl}_2 \rightarrow \text{RCOCl} + \text{SO}_2\uparrow + \text{HCl}\uparrow$

• Preferred method: gaseous byproducts

5. Acyl Chloride via PCl5: $\text{RCOOH} + \text{PCl}_5 \rightarrow \text{RCOCl} + \text{POCl}_3 + \text{HCl}$

• Less preferred: POCl3 (liquid) is hard to remove

6. LiAlH4 Reduction: $\text{RCOOH} \xrightarrow{\text{LiAlH}_4, \text{dry ether}} \text{RCH}_2\text{OH}$

• NaBH4 gives NO reaction with RCOOH

7. Kolbe Electrolysis: $2\text{RCOO}^- \xrightarrow{\text{electrolysis}} \text{R-R} + 2\text{CO}_2$

• Occurs at anode (oxidation)
• Product: symmetrical alkane

8. Grignard Carboxylation: $\text{RMgX} + \text{CO}_2 \xrightarrow{\text{dry ether}} \text{RCOOMgX} \xrightarrow{\text{H}_3\text{O}^+} \text{RCOOH}$

• Adds one carbon (–COOH) to the chain

9. Nitrile Hydrolysis: $\text{RCN} + \text{H}_3\text{O}^+ \xrightarrow{\text{reflux}} \text{RCOOH} + \text{NH}_4^+$

10. Saponification: $\text{RCOOR'} + \text{NaOH} \xrightarrow{\text{reflux}} \text{RCOONa} + \text{R'OH}$

• Irreversible (contrast with Fischer esterification)

Key Data Table