Chapter 16: PROBLEM 16.8 (page 612)
Question. Draw all possible resonance structures for the following cation and indicate which structure makes the largest contribution to the resonance hybrid.

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Chapter 16: PROBLEM 16.8 (page 612)
Question. Draw all possible resonance structures for the following cation and indicate which structure makes the largest contribution to the resonance hybrid.

Answer
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Question: Draw the products of the following Diels–Alder reactions. Indicate stereochemistry where appropriate.
a.

b.

c.

d.

Question: One step in the synthesis of dodecahedrane (Section 4.11) involved reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4 . This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.

Question: Classify each diene as isolated or conjugated.
a.

b.

c.

d.

Question: Draw all possible stereoisomers of hepta-2,4-diene and label each double bond as E or Z.
Question: Devise a stepwise mechanism for the conversion of M to N. N has been converted in several steps to lysergic acid, a naturally occurring precursor of the hallucinogen LSD (Figure 18.4).

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