JEE Main202330 Jan 2023Evening ShiftChemistryHaloalkanes and HaloarenesActual
In the above conversion of compound ( X ) to product ( Y ), the sequence of reagents to be used will be:
Options
- A(i) Br 2 ,   Fe (ii) Fe ,   H + (iii) LiAlH 4
- B(i) Br 2 aq (ii) LiAlH 4 (iii) H 3 O +
- C(i) Fe ,   H + (ii) Br 2 aq (iii) HNO 2 (iv) CuBr
- D(i) Fe ,   H + (ii) Br 2 aq (iii) HNO 2 (iv) H 3 PO 2
Correct answer
D. (i) Fe ,   H + (ii) Br 2 aq (iii) HNO 2 (iv) H 3 PO 2
Step-by-step solution
The nitro group on the benzene ring is reduced to amine group with metal and acid. Now, the methyl and nitro groups present on the benzene ring are ortho-para directing groups and amine group is the strong activator. Hence, bromine water reacts with respect to amino group. The amino group on the benzene ring undergoes diazotization with nitrous acid. The diazonium part reduces to benzene with hypophosphorous acid.