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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 following reaction involves two successive intramolecular Michael reactions. Write both steps, and show their mechanisms.

In the mixed Claisen reaction of cyclopentanone with ethyl format, a much higher yield of the desired product is obtained by first mixing the two carbonyl components and then adding a base, rather than by first mixing base with cyclopentanone and then adding ethyl format. Explain.

How might the following compounds be prepared using Michael reactions? Show the nucleophilic donor and the electrophilic acceptor in each case.

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.

Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction.

(a) Trimethyl acetaldehyde

(b) Cyclobutanone

(c) Benzophenone (diphenyl ketone)

(d) 3-Pentanone

(e) Decanal

(f) 3-Phenyl-2-propenal
See all solutions

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