Question

How can you convert benzene to the following compounds using this list of reagents?

1. HNO₃, H₂SO₄   2. SO₃, H₂SO₄    3. NaNO₂, HCl    4. Br₂, FeBr₃    5. Cl₂, FeCl₃

6. CuCN    7. CuCl    8. CuBr    9. H₂O, ∆    10. CH₃CH₂CH₂Cl, AlCl3

11. CH₃CH₂COCl (an acid chloride), AlCl₃   12. Zn-Hg, EtOH, HCl   13. (1. Sn, HCl 2. NaOH, H₂O)

14. CH₃Cl , AlCl₃      15. KMnO₄

A) m-nitropropylbenzene

B) p-nitropropylbenzene

I tried 1, 10 for the first one and 10, 1 for the second one (since I know NO₂ is meta directing, and propane is ortho, para directing) but those are wrong, and I'm not sure why.

Answer 1

benzene react with CH3CH2COCl (an acid chloride), AlCl3 to give 1-phenylpropan-1-one.

propan-1-one are meta directing group

1-phenylpropan-1-one undergo nitration with HNO3, H2SO4 to give 1-(3-nitrophenyl)propan-1-one

1-(3-nitrophenyl)propan-1-one will undergoes Clemmensen Reduction (Zn-Hg, EtOH, HCl to give m-nitropropylbenzene

B) m-nitropropylbenzene

benzene react with CH3CH2COCl (an acid chloride), AlCl3 to give 1-phenylpropan-1-one it will undergoes Clemmensen Reduction (Zn-Hg, EtOH, HCl) to give propylbenzene . propyl are o, p directing group,

propylbenzene one undergo nitration with HNO3, H2SO4 to give p-nitropropylbenzene major   and o-nitropropylbenzene minor