TUTORIAL 6

1. Give IUPAC names for the following compounds:

2. Which of the following molecules would you expect to be aromatic?

3. Propose structures for aromatic hydrocarbons that meet the following descriptions:
a. C9H12; gives only one C9H11Br product on substitution with bromine.
b. C10H14; gives only one C10H13Cl product on substitution with chlorine
c. C8H10; gives three C8H9Br products on substitution with bromine
d. C10H14; gives two C10H13Cl products on substitution with chlorine

4. Predict the major monoalkylation products you would expect to obtain from reaction
of the following substances with chloromethane and AlCl3:
a. m-Bromophenol
b. 2,4-Dichloronitrobenzene
c. 2,4-Dichlorophenol
5. Name and draw the major product(s) of electrophilic chlorination of the following
compounds:
a. o-Xylene
b. p-Nitrobenzoic acid
c. p-Bromobenzenesulfonic acid

6. What product(s) would you expect to obtain from the following reactions?

7. The nitration of toluene can occur either ortho, meta or para to the methyl group.
Determine and justify the most likely product(s) with respect to resonance stability.

8. Propose structures for compounds G-I: