CHEM1280 Problem Set 3

(Due on 10. Oct, 2012)

1. Tell whether each of the following compounds has the E or the Z configuration:

a. Z b.E

2. a. Give the structures and the systematic names for all alkenes with molecular formula
C4H8, ignoring cis-trans isomers.

b. Which of the above compounds have E and Z isomers?

3. Identify the electrophile and the nucleophile in each of the following reaction steps.
Then draw curved arrows to illustrate the bond-making and bond-breaking processes.
4. What will be the major product of the reaction of 2-methyl-2-butene with each of
following reagents?
a. HBr d. H2O + trace H2SO4
b. HI e. CH3OH + trace H2SO4
c. H2, Pd/C f. CH3CH2OH + trace H2SO4

5. Starting with an alkene, indicate how each of the following compounds can be
synthesized:
6. What reagents could be used to carry out the following synthesis?

7. Which of the following systematic names are correct? Correct the incorrect names.
a. 4-heptyne d. 2,3-dimethyl-5-octyne
b. 2-ethyl-3-hexyne e. 4,4-dimethyl-2-pentyne
c. 4-chloro-2-pentyne f. 2,5-dimethyl-3-hexyne

a. 3-heptyne d. 6,7-dimethyl-3-octyne
b. 5-methyl-3-heptyne e. correct
c. correct f. correct

8. Show how each of the following compounds could be prepared using the given starting
material, any necessary inorganic reagents, and any necessary compound that has no
more than four carbon atoms. (More than one step may be necessary)