Questions (fill in the blanks):

1. The general formula of a carboxylic acid is ________.
2. The pKa of acetic acid is approximately ________.
3. The carboxylate ion (RCOO–) has each C–O bond with bond order ________.
4. The acidity ladder: RCOOH () > ArOH (__) > H2O () > ROH () > RC≡CH ().
5. Among Cl3CCOOH, Cl2CHCOOH, ClCH2COOH, and CH3COOH, the strongest acid is ________ (pKa ____).
6. Among Cl3CCOOH, Cl2CHCOOH, ClCH2COOH, and CH3COOH, the weakest acid is ________.
7. The HVZ reaction uses ________ and ________ as reagents.
8. The HVZ reaction halogenates the ________ position of the carboxylic acid.
9. ________ acid and ________ acid CANNOT undergo HVZ because they lack alpha-H.
10. The reducing agent that can reduce carboxylic acids to primary alcohols is ________.
11. The reducing agent that CANNOT reduce carboxylic acids is ________.
12. Fischer esterification is a ________ $\frac{reversible}{irreversible}$ reaction.
13. Saponification of RCOOR' with NaOH gives ________ + ________.
14. The reagent SOCl2 converts RCOOH to ________ with byproducts ________ and ________.
15. Soda lime = ________ + ________.
16. Soda lime decarboxylation: RCOONa + NaOH/CaO → ________ + Na2CO3.
17. Kolbe electrolysis occurs at the ________ $\frac{anode}{cathode}$.
18. Kolbe electrolysis: 2 RCOO– → ________ + 2 CO2.
19. Grignard synthesis: RMgX + ________ → RCOOMgX → (H3O+) → RCOOH.
20. Nitrile hydrolysis (acidic): RCN + H3O+ → ________ + NH4+.
21. The pKa of formic acid is ________, making it ________ $\frac{stronger}{weaker}$ than acetic acid.
22. The +I effect of alkyl groups ________ $\frac{increases}{decreases}$ carboxylic acid acidity.
23. The –I effect of halogens ________ $\frac{increases}{decreases}$ carboxylic acid acidity.
24. 2-Chlorobutanoic acid is ________ $\frac{more}{less}$ acidic than 3-chlorobutanoic acid.
25. The SMILES for benzoic acid is ________.
26. NEET trap: acetic acid + NaBH4 gives ________.
27. The byproducts of PCl5 reaction with RCOOH are ________ and ________.
28. Kolbe electrolysis of sodium propanoate gives ________ and ________.
29. The SMILES for ethyl acetate is ________.
30. Formic acid SMILES = ________, acetic acid SMILES = ________.

Answer Key:

1. RCOOH
2. 4.76
3. 1.5
4. 4–5; ~10; 15.7; 16–18; ~25
5. Cl3CCOOH; pKa 0.65
6. CH3COOH (pKa 4.76) — or (CH3)3CCOOH if included
7. X2 (halogen); red phosphorus (Red P)
8. alpha (C-2)
9. Formic; benzoic
10. LiAlH4
11. NaBH4
12. Reversible
13. RCOONa (carboxylate salt); R'OH (alcohol)
14. RCOCl (acyl chloride); SO2; HCl
15. NaOH; CaO
16. R–H (alkane with n–1 carbons)
17. Anode
18. R–R (symmetrical alkane)
19. CO2 (dry)
20. RCOOH
21. 3.75; stronger
22. Decreases
23. Increases
24. More
25. OC(=O)c1ccccc1
26. No reaction
27. POCl3; HCl
28. Butane (C4H10); CO2
29. CCOC(=O)C
30. OC=O; CC(=O)O