CHEM 3312: General Organic Chemistry

Homework Assignment 3, Due October 12

Below is the structure of androstenedione, a compound commonly seen in the news several baseball seasons ago.

1. Indicate the presence of polar bonds in androstenedione by drawing in bond dipoles. Also label partially charged atoms using the d⁺ or d^- notation.

Reference textbook problems: 2.1, 2.2, 2.3, 2.4, 2.5, 2.6

2. Identify the hydrogens in androstenedione that are more acidic than standard alkyl hydrogens (i.e. those having pKa of 20 or smaller).

Reference textbook problems: 22.1, 22.8, 22.24, 22.28

3. Draw any enolate anions (and their resonance structures) that could form if androstenedione were treated with a base (such as NaOH). (Note, you should have 3 different enolate anions).

Reference textbook problems: 22.9, 22.23, 22.25

4. Draw any enols that could form under acidic conditions.

Reference textbook problems: 22.2, 22.3,

5. If androstenedione were treated with bromine (Br₂) in acetic acid, what product or products would be generated?

Reference textbook problems: 22.12, 22.13