Consider the following organic reaction sequence. Choose the final product (X) from the following (consider the major product in all intermediate reactions) [figure]
- Benzene
- Phenol
- Propanol
- Chlorobenzene
Answer
(1) Benzene
Solution
(i) CH3CH2COOH NH3, CH3CH2CONH2 (propanamide)
(ii) Hofmann bromamide degradation: CH3CH2CONH2 Br2/NaOH CH3CH2NH2 (ethanamine)
(iii) 1° aliphatic amine + nitrous acid: CH3CH2NH2 HNO2, H2O CH3CH2OH + N2
(iv) As per NCERT, ethanol reduces a diazonium salt to the arene:
C6H5N2+Cl- + CH3CH2OH C6H6 + N2 + CH3CHO + HCl
∴ X = benzene
Answer: (1)