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Chapter 24: Q.10. (page 962)

Question: What carbonyl starting materials are needed to prepare each compound using a directed aldol reaction?

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Aldol reaction

An aldol reaction involves the formation of a β-hydroxy carbonyl compound from two carbonyl compounds (aldehyde or ketone).

02

General aldol reaction

A general aldol reaction is given below:

Aldol reaction

03

Carbonyl compounds used to prepare the given compounds

Cleaving the carbon-carbon (C-C) bond between the carbon adjacent to the carbonyl compound and the one connected to the hydroxyl group and replacing the alcohol group with a carbonyl group gives the structure of the starting materials used.

a.

Cleavage of C-C bond in a.

The starting materials required are cyclohexanone and 2-methyl propanal.

b.

Cleavage of C-C bond in b.

The starting materials required are phenylacetaldehyde and ketone.

c.

Cleavage of C-C bond in c.

The starting materials required are 4-heptanone and benzaldehyde.

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Most popular questions from this chapter

Question: Which carbonyl compounds do not undergo an aldol reaction when treated with OH- in H2O ?

Question:When A is treated with aqueous –OH, the major product is compound B, which undergoes ester hydrolysis and decarboxylation to form C. Draw a stepwise mechanism for the conversion of A to B.

Question: What product (including stereochemistry) is formed in each of the following intramolecular reactions?

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: What β-keto ester is formed when each ester is used in a Claisen reaction?
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