Draw the least and most stable Newman projection and sawhorse representation of 4-bromo-3-chloroheptane. and 1,4-dichlorcyclohexane. Label each.

a. Write out the complete mechanism for the nitration of toluene. Include the formation of the elctrophile, the addition of the electrophile, the resonance structures of the intermediate carbocation, and the elimination of a proton to form the aromatic ring.

b. Rewrite the resonance structures for the intermediate carbocation with the assumption that the entering nitro group adds meta to the -CH3 substituent.

c. Examine the intermediate carbocations formed from a/b. Suggest a reason why toluene is either meta or ortho/para directing.
II. How would you prepare salicylic acid from benzene?