Amongst the following, the total number of compounds soluble in aqueous NaOH at room temperature is: [figure]
- 5
- 4
- 6
- 3
Answer
(1) 5
Solution
A compound dissolves in aqueous NaOH only if it is acidic enough to form a water-soluble sodium salt, i.e. phenols (pKa 10) and carboxylic acids (pKa 4–5).
Soluble: (I) 1-naphthol – phenol; (II) naphthalene-1-carboxylic acid – acid; (IV) 4-(dimethylamino)phenol – phenol; (V) 4-methylphenol – phenol; (VIII) benzoic acid – acid.
e.g. C6H5COOH + NaOH C6H5COO-Na+ + H2O
Insoluble: (III) naphthalen-1-ylmethanol – alcohol, much weaker acid than water; (VI) 1,4-di-tert-butylbenzene – hydrocarbon; (VII) benzaldehyde – no acidic H; (IX) N,N-dimethylcyclohexanamine – base.
∴ Total = 5
Answer: (1)