Chem 31 PS1

1. Consider the structure of procaine:

a. Identify ALL the functional groups present in procaine.

b. How many atoms in the molecule are (i) sp-hybridized, (ii) sp2-hybridized, (ii) sp3-hybridized?
c. Arrange the following bonds in terms of INCREASING bond strength:
C1-C2, C3-N, C4-O, C5-O, C5=O, C5-C6, C9-N, C10=C11
2. Arrange the following compounds in terms of INCREASING melting point temperature:
a. 2,2,3-trimethylbutane; 2,3-dimethylpentane, hexane
b. (4E)-oct-4-ene, (4Z)-oct-4-ene, (3E)-3-methylhept-3-ene, (3Z)-3-methylhept-3-ene
c. butane, 1-butene, 1-butyne, buta-1,3-diene
3.

Identify the type of organic reaction (addition, elimination, substitution) of the following:
a. 1,2-dihydroxylation of alkenes using cold, alkaline KMnO4 and acidic water.
b. Hydrogenation of alkynes using Lindlars catalyst.
c. Formation of alkyl halides from alkanes via free radical mechanism.

4. Consider the compound (3S)-3,4,4-trimethylheptane:

a. Draw the most stable intermediate formed when the compound reacts with Br2.
b. A pair of enantiomers is expected to form in 4a. Rationalize this result.
c. Draw the most stable conformation of the (R)-product at the C3-C4 bond.
5. Draw an (a) enantiomer, (b) diastereomer of the compound below.

6. Consider the compound below:

a. What is the name (including stereochemistry) of this compound?

b. Draw its product (in its most stable conformation) when reacted with cold, alkaline KMnO4.
7. All of these compounds are formed via cationic polymerization. Determine the monomer in each of the
following:

a.

b.
8. In each pair for compounds, determine which is AROMATIC:

a.

b.
9. Draw the missing substrate(s), reagent(s), intermediate(s) or product(s). Show stereochemistry.