TUTORIAL 8

1. Give IUPAC names for the following structures:

2. Predict the products of the reaction of (i) phenylacetaldehyde and (ii) acetophenone with
the following reagents:
a. NaBH4, then H3O+
b. Tollens’ reagent
c. NH2OH, HCl catalyst
d. CH3MgBr, then H3O+
e. 2 CH3OH, HCl catalyst
f. H2NNH2, KOH
g. (C6H5)3P=CH2
h. HCN, KCN

3. How would you carry out the following reactions? More than one step may be required.
a. 3-Hexyne  3-Hexanone
b. Bromobenzene  Acetophenone
c. 1-Methylcyclohexene  2-Methylcyclohexanone

4. Each of the following reaction schemes contains one or more flaws. What is wrong in
each case? How would you correct each scheme?
a.

b.
5. Write a mechanism for the following reaction. Include formal charges and curved arrows
to show the movement of electrons in all steps.