Consider the following reactions. From these reactions which reaction will give carboxylic acid as a major product? Choose the correct answer from the options given below:
- A, B and E only
- A and D only
- B, C and E only
- B and E only
Answer
(4) B and E only
Solution
(A) Partial (mild) hydrolysis of a nitrile stops at the amide: R-C N H+/H2O R-CONH2. Not an acid.
(B) Grignard reagent adds to CO2; hydrolysis gives the acid: R-MgX CO2 R-COOMgX H3O+ R-COOH. Acid.
(C) Stephen reduction: SnCl2/HCl gives the imine salt, hydrolysis gives the aldehyde R-CHO. Not an acid.
(D) PCC oxidises a 1° alcohol only up to the aldehyde R-CHO. Not an acid.
(E) Rosenmund reduction (H2, Pd–BaSO4) gives benzaldehyde; bromine water then oxidises the aldehyde to benzoic acid:
C6H5COCl H2, Pd-BaSO4 C6H5CHO Br2 water C6H5COOH. Acid.
B and E only.
Answer: (4)