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Chapter 24: Q.36. (page 962)

Question: Identify the structures of C and D in the following reaction sequence.

Short Answer

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Answer

Structures of C and D

Step by step solution

01

Role of dimethyl sulfide

The dimethyl sulfide reduces one oxygen atom from the trioxolane intermediate formed upon ozonolysis.

02

Ozonolysis

Upon ozonolysis, the C=C double bond cleaves, and both the carbons get a (=O) bond.

03

Product of the given reaction

C is a product of the ozonolysis reaction, while D is an aldol product. Both of the products are given hereunder.

Structures of C and D

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Most popular questions from this chapter

  1. Question:β -Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds usedin traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular 00a00000ldol reaction.000 (a) What Michael acceptor is needed for the conjugate addition? (See Problem23.61 for another method to form the bicyclic ring system of β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.

Question: Draw a stepwise mechanism for the following Robinson annulation. This reaction was a key step in a synthesis of the steroid cortisone by R. B. Woodward and co-workers at Harvard University in 1951.

Question: What cyclic product is formed when each 1,5-dicarbonyl compound is treated with aqueous OH?

Question:What starting materials are needed to synthesize each compound using a Robinson annulation?

Question: In theory, the intramolecular aldol reaction of 6-oxoheptanal could yield the three compounds shown. It turns out, though, that 1-acetylcyclopentene is by far the major product. Why are the other two compounds formed in only minor amounts? Draw a stepwise mechanism to show how all three products are formed.
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