Problem Set 6
Chapter 7
Due: Monday, October 22, 2001
August Wilhelm von Hofmann (1818-1892) Royal College of Chemistry (1845) Berlin (1865) |
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. |
Aleksandr Mikhailovich Zaitsev [Saytzeff (German)] (1841-1910) University of Kazan |
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? |
8. Compound A, C8H12, reacts with hydrogen in the presence of the catalyst Pt to afford B, C8H14. [How many rings and double bonds in A and B?] Compound B forms only 2 monochloro derivatives, C and D, upon free radical chlorination. Compound C forms A and alcohol E (C8H12O) upon reaction with KOH. Compound D cannot undergo an SN2 reaction (why?) with KOH nor can it undergo elimination. What are the structures of A-E? Show your reasoning. |
9. Predict the products of the reaction on the right. Provide a mechanism. |
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