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Chapter 24: Q.46. (page 962)

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

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

The Robinson annulation

The Robinson annulation involves the formation of a six membered cyclic ring from an 伪,尾-unsaturated ketone and an enolate forming carbonyl compound. The steps in Robinson Annulation involve Michael addition followed by Aldol condensation.

An example is shown below:

Example of Robinson Annulation

02

Retrosynthetic analysis

a.

The retrosynthetic breakdown of the target molecule gives the following starting materials:

Starting materials of a

b.

The following starting materials are obtained upon retrosynthetic analysis:

Starting materials of b

c.

The following started materials undergo Robinson annulation to give the given product:

Starting materials of c

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Most popular questions from this chapter

Question:Draw the product formed from a Michael reaction with the given starting materials usingOEt,EtOH.

Question: Answer the following questions about 2-acetylcyclopentanone.

a. What starting materials are needed to form 2-acetylcyclopentanone by a Claisen reaction that forms bond (a)?

b. What starting materials are needed to form 2-acetylcyclopentanone by a Claisen reaction that forms bond (b)?

c. What product is formed when 2-acetylcyclopentanone is treated with NaOCH2CH3, followed by CH3I?

d. Draw the Robinson annulation product(s) formed by reaction of 2-acetylcyclopentanone with methyl vinyl ketone (CH2=CHCOCH3).

e. Draw the structure of the most stable enol tautomer(s).

Question: Which of the following compounds can serve as Michael acceptors?

Question: What starting materials are needed to synthesize each compound using an aldol or similar reaction?

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.
See all solutions

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