Tutorial 7 – Organohalide and Alcohol

1. Give IUPAC names for the following compounds:

a) b) c)

d) e) f)

g) h) i)

2. How would you prepare the following compounds, starting with cyclopentene
and any other reagents needed?
a) Chlorocyclopentane
b) Methylcyclopentane
c) 3-Bromocyclopentene
d) Cyclopentanol
e) Cyclopentylcyclopentane
f) 1,3-Cyclopentadiene

3. A chemist requires a large amount of 1-bromo-2-pentene as starting material for a

synthesis and decides to carry out an NBS allylic bromination reaction. What is wrong
with the following synthesis plan? What side products would form in addition to the
desired product?

4. What product(s) would you expect from the reaction of 1-methylcyclohexene with NBS?
Would you use this reaction as part of a synthesis?

5. Rank the compounds in each of the following series in order of increasing oxidation
level:
a)
 b)

6. How would you carry out the following syntheses?

7. The syntheses shown here are unlikely to occur as written. What is wrong with each?
a)

b)

c)

8. Provide the alkene needed to synthesize each of the following alcohols by using either
oxymercuration–demercuration or hydroboration–oxidation method.
a) b) c)

d) e) f)
9. How would you prepare the following compounds from 2-phenylethanol? More than one
step may be required.
a) Styrene (PhCH=CH2)
b) Phenylacetic acid (PhCH2CO2H)
c) Benzoic acid
d) Ethylbenzene
e) Benzaldehyde
f) 1-Phenylethanol
g) 1-Bromo-2-phenylethane

10. Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 25 °C to yield a mixture
of two alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after
ozone treatment followed by reduction with zinc in acetic acid. Write the reactions
involved, and identify A and B.