1. A Review of General Chemistry

There is a small portion of the periodic table that you must know to do organic chemistry. Construct this part from ­memory, using the following steps.

a. From memory, make a list of the elements in the first two rows of the periodic table, together with their numbers of valence electrons

b. Use this list to construct the first two rows of the periodic table.

c. Organic compounds often contain sulfur, phosphorus, chlorine, bromine, and iodine. Add these elements to your ­periodic table.

a. Draw resonance contributors for the following species. Do not include structures that are so unstable that their contributions to the resonance hybrid would be negligible. Indicate which are major contributors and which are minor contributors to the resonance hybrid.

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

6.

Compound X, isolated from lanolin (sheep’s wool fat), has the pungent aroma of dirty sweatsocks. A careful analysis showed that compound X contains 62.0% carbon and 10.4% hydrogen. No nitrogen or halogen was found.

a. Compute an empirical formula for compound X

In 1934, Edward A. Doisy of Washington University extracted 3000 lb of hog ovaries to isolate a few milligrams of pure estradiol, a potent female hormone. Doisy burned 5.00 mg of this precious sample in oxygen and found that 14.54 mg of CO₂ and 3.97 mg of H₂O were generated.

a. Determine the empirical formula of estradiol.