Q.

Derive a series of reactions to convert benzene into metachlorobromobenzene. Select reagents and conditions from the following table, listing them in the order of use.

(1) sulphuric acid (conc.), heat

(2) Cl2+FeCl3 and heat 

(3) NaNO2+H3O+,0oC
(4) H2,Pd/C catalyst 
(5) Mg in ether
(6) PBr3
(7) H3PO2
(8) HNO3 (conc.) +H2SO4 (conc.) and heat 
(9) Cu2Br2+HBr
(10) CH3CO2O+ pyridine 

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a

8 then 4 then 10 then 2 then 3 then 9

b

8 then 2 then 4 then 3 then 9

c

1 then 2 then 6

d

2 then 8 then 4 then 3 then 9

answer is A.

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