Exam 1 -09

Exam 1 -09 - 1 (18 points). Are the following compounds...

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1 (18 points). Are the following compounds planar? By “planar,” we mean that all the non-hydrogen atoms lie in the same plane. Explain why or why not. O O N B N B N B H H H H H H N H (a) (b) (c) (d) (e) In the case of (e) would the observation that there is no signal in the 1 H NMR spectrum below δ = 5.5 ppm indicate planarity or nonplanarity? Explain your answer briefly. a. b.
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c. d. e.
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2 (16 points). Predict the relative rates of Diels-Alder reaction of the following dienes. Explain your reasoning briefly. First, write 1, 2, 3, or 4 in the box over the structure. 1 = Fastest, 4 = Slowest
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1 ) to give two Diels-Alder adducts, 2 and 3. Adduct 2 is favored at low temperature and adduct 3 is favored at high temperature. O O O 1 2 major product at low temperature 3 major product at high temperature + a. Draw very detailed three-dimensional pictures of the two adducts. No ambiguous structures, please. You must show stereochemistry very carefully. It will probably – no,
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Exam 1 -09 - 1 (18 points). Are the following compounds...

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