Exercise 5 | Electrophilic Attack on Derivatives of Benzene

Propose a reasonable synthesis of the following compounds from benzene:
 

1) The 2 substituents are para oriented.
CH3: Ortho, Para Directing; COCH3: Meta Directing ⇒ start with CH3
 

 

2) The 2 substituents are meta oriented.
Cl: Ortho, Para Directing; NO2: Meta Directing ⇒ start with NO2
 

 

3) Cl and CH3 are Ortho Para Directing ⇒ start with CH3 and block Para position with an e- acceptor