Q18 / 90 · JEE Main 2023 (30 Jan Shift 2) · Chemistry

Figure

In the above conversion of compound (X) to product (Y), the sequence of reagents to be used will be:

  • A

    (i) Br2, Fe

    (ii) Fe, H+

    (iii) LiAlH4

  • B

    (i) Br2aq

    (ii) LiAlH4

    (iii) H3O+

  • C

    (i) Fe, H+

    (ii) Br2aq

    (iii) HNO2

    (iv) CuBr

  • Correct answer
    D

    (i) Fe, H+

    (ii) Br2aq

    (iii) HNO2

    (iv) H3PO2

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.

Figure 

Hence, the correct answer is option: 'D'.

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