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Chapter 17: Q-17-73P (page 850)

Show how the following compound can be prepared from starting materials that have no more than five carbons:

Short Answer

Expert verified

If an aldol addition uses two different carbonyl compounds, such reactions are crossed aldol addition.

A single product can be obtained in this reaction if one of the aldehydes does not comprise alpha hydrogen and cannot form an enolate ion.

Step by step solution

01

Crossed Aldol addition

If an aldol addition uses two different carbonyl compounds, such reactions are crossed aldol addition.

A single product can be obtained in this reaction if one of the aldehydes does not comprise alpha hydrogen and cannot form an enolate ion.

02

Identifying how the given compound can be prepared from starting materials that have no more than five carbons

The given compound is prepared from the starting material with no more than five carbons through a series of steps. An - unsaturated carbonyl compound is reacted with a base leading to the formation of an enolate ion.

This ion attacks another cyclic unsaturated compound. An intramolecular cyclization happens in the last transformation, and the formation of the required compound takes place. The reaction is given below.

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Most popular questions from this chapter

Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones?

a. 2-pentanone b. 2-octanone c. 4-phenyl-2-butanone

If the preference for formation of a six-membered ring were not so great, what other cyclic product would be formed from the intramolecular aldol addition of

a.2,6-heptanedione? b. 2,8-nonanedione?

Describe three ways to synthesize the following compound:

Draw the products of the following reactions:
See all solutions

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