a) Complete the following: i) CH₃CN →1. DIBAL-H 2. H₂O→ 'A' →NH₂OH/H⁺→ 'B' ii) Write the IUPAC name of the compound shown in the figure (3-bromobenzaldehyde). iii) Write a chemical test to distinguish between phenol and benzoic acid.(a)(ii): structure to name
Answer: A = CH₃CHO; B = acetaldoxime CH₃CH=NOH. (ii) 3-Bromobenzaldehyde. (iii) NaHCO₃ — effervescence with benzoic acid only.
Solution
(i) DIBAL-H half-reduces the nitrile; hydrolysis gives the aldehyde: