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Chapter 24: Q.33. (page 962)

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

Short Answer

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Answer

Step by step solution

01

Identify the α and β  carbons to the carbonyl group

The bond between the αandβcarbons to the carbonyl group is cleaved. The α-carbon is then added with a hydrogen atom.

02

Addition to the  β-carbon

Upon the cleavage of the bond between the αandβ carbons, the role="math" localid="1649052581778" β-carbon is added with a =Oif the bond between the αandβ carbons was a double bond.

However, if the αandβ carbons had a single bond then, the OH group on the β-carbon is converted to the carbonyl C=O group.

03

Product of the given reaction

a. The starting materials of the product are detected hereunder.

starting materials of a.


b. The starting materials of the product are detected hereunder.

starting materials of b.


c. The starting materials of the product are detected hereunder.

starting materials of c.


d. The starting materials of the product are detected hereunder.

starting materials of d.

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Most popular questions from this chapter

Question:One step in a recent short synthesis of a prostaglandin (Section 19.6) involves the conversion of succinaldehyde to the bicyclic hemiacetal X. Draw a stepwise mechanism for this process. (Hint: The mechanism begins with an intermolecular aldol reaction.)

Question: Zingerone, a spicy-sweet component of cooked ginger, can be converted to its protected TBDMS ether A, as we learned in Chapter 20. How can A be converted to gingerol, a compound present in fresh ginger, using a directed aldol reaction as a key step?

Question: Draw the product formed when each dicarbonyl compound undergoes an intramolecular aldol reaction followed by dehydration.

Question: Draw a stepwise mechanism for the following reaction, which was used in the synthesis of ezetimibe (Section 20.6), a drug used to treat patients with high cholesterol.

Question: 2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasmine-like odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reaction between benzaldehyde (C6H5CHO)and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.
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