1. Learn how to determine the Degree of Unsaturation of a compound from its formula. We will be using this concept in class. The text uses a formula. I think the website method is easier. Try this one: C₁₂H₁₇Br₂ClN₂O₂S.

2. Do problems 2-4 in the Alkyl Halide module in ORGO. They need not appear on your homework.

3. Construct a diagram [like the one here] that interrelates the heats of formation and the heats of hydrogenation (Table 7-1, pg. 307) of (E)-2-hexene, (Z)-2-hexene and n-hexane, and the standard state. Provide numerical values. Do your values for the heats of hydrogenation make sense with relevant data in Table 7-1, pg. 307?

4. Determine the heat of formation of 2-methyl-2-butane given the data provided in Table 7-1, pg. 307, and the heats of formation provided in the Study Aids.

5. Treatment of (3S, 4S)-3-bromo-3,4-dimethylhexane A with aqueous sodium hydroxide gives a tetrasubstituted alkene B, an optically active (E)-trisubstituted alkene C and a small amount of an optically active alkene D. Why is (E)-C favored over (Z)-C? Does the racemate of A give the same products? Explain. When the diastereomer (3R, 4S)-A is used in the reaction, what are the structures of B', C' and D'?

6. Treatment of bromide 1 with t-C₄H₉OK gives only bicyclic alkene 2. Bromide 3 is unreactive under the same conditions. Explain. Provide an accurate mechanism for the formation of 2 from 1.

7. A student decides to synthesize tert-butyl methyl ether (MTBE) by the reaction of tert-butyl chloride with CH₃ONa in CH₃OH. His classmate tells him that his experiemnt is doomed to failure. She, being well-informed and generous, offers two alternative methods for the solution of his synthesis. Where did he go wrong and what did she offer as alternatives?