1. Draw Lewis structures for methane and its carbocation, radical, and carbanion.

2. Draw Lewis structures for cyanamide (NH₂CN) and hydrazoic acid (HN₃).

3. Explain and illustrate with Lewis structures why BF₃ forms a "salt" (bp 126^o) with diethyl ether.

4. Explain and illustrate the difference between tautomerism and resonance.

5. Draw the structure and correct IUPAC name for "2-isopropyl-2-isobutyl-n-butane".

6. Carbon dioxide and water are the products of complete combustion (oxidation) of

hydrocarbons. How much CO₂ and H₂O is produced by the oxidation of 1 gram of

cyclohexane? Show how these numbers can be used to determine the

carbon/hydrogen ratio (empirical formula) if the cyclohexane were an unknown

substance. What information is necessary to obtain the molecular formula?

7. Ammonia, NH₃, has a pKa=33. Can a solution of NaNH₂ be prepared in methanol (CH₃OH)? Explain.

8. A chemical reaction obeys the rate law, rate =k[A][B]. What impact will doubling the amount of

solvent have on the rate of the reaction? Explain.

9. A better acronym for Organic Reactions for Bulldogs (ORB) at the course website is needed. Since

Bulldogs refer to the course as ORGO, it is an acronym in search of a title. Other meaningful and

printable acronyms may be suggested. Mail via ORB (in the About ORB link). A vote will be taken on a

future Problem Set.