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Chapter 23: Q50E (page 783)

What product would you expect to obtain from aldol cyclization of hexanedial,OHCCH2CH2CH2CH2CHO

Short Answer

Expert verified

Aldol cyclization of hexanedial, OHCCH2CH2CH2CH2CHOgenerally gives five-member ring aldehydic compounds.

Step by step solution

01

Cyclization in hexanedial

In Hexanedial, cyclization is undergone through intramolecular aldol reaction in which reaction occurs within the same compound and a high member ring is formed which is strain-free and stable.

02

Intramolecular aldol reaction in Hexanedial:

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Most popular questions from this chapter

The Mannich reaction of a ketone, an amine, and an aldehyde is one of the few three-component reactions in organic chemistry. Cyclohexanone, for example, reacts with dimethylamine and acetaldehyde to yield an amino ketone. The reaction takes place in two steps, both of which are typical carbonyl-group reactions.

(a)The first step is reaction between the aldehyde and the amine to yield an intermediate iminium ion R2C=NR2+plus water. Propose a mechanism, and show the structure of the intermediate iminium ion.

(b)The second step is reaction between the iminium ion intermediate and the ketone to yield the final product. Propose a mechanism.

Predict the addition product for each reaction below and provide the mechanism.

Azlactones are important starting materials used in the synthesis of dehydro a-aminoacids. They react with aldehydes to form an intermediate that is hydrolyzed under acidic conditions to give the final amino acid product. Provide the structure of the intermediate and propose a mechanism for its formation.

What enone product would you expect from aldol condensation of each of the following compounds?

1-Butanol is prepared commercially by a route that begins with an aldol reaction. Show the steps that are likely to be involved.
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