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Chapter 23: Q27E (page 783)

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

Short Answer

Expert verified

The product formed from the reactions are as follows,

  1. 2-ethyl-3-hydroxyhexanal
  2. 1’-hydroxy-[1,1’-(cyclobutan-2-one)
  3. 3-hydroxy-3-phenylpropanal
  4. 3-hydroxy-3-methylcyclopentanone

Step by step solution

01

Product formed from reaction (a)

The product formed from the given reaction is,

The mechanism for the above reaction is as follows,

02

Product formed from reaction (b)

The product formed from the given reaction is,

The mechanism for the above reaction is as follows,

03

Product formed from reaction (c)

The product formed from the given reaction is,

The mechanism for the above reaction is as follows,

04

Product formed from reaction (d)

The product formed from the given reaction is,

The mechanism for the reaction is as follows,

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Most popular questions from this chapter

When 2-methyl cyclohexanone is converted into an enamine, only one product is formed despite the fact that the starting ketone is unsymmetrical. Build molecular models of the two possible products and explain the fact that the sole product is the one with the double bond opposite the methyl-substituted carbon.

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

Intramolecular aldol cyclization of 2,5-heptanedione with aqueous NaOH yields a mixture of two enone products in the approximate ratio 9;1. Write their structures, and show how each is formed.

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.

The major product formed by intramolecular aldol cyclization of 2,5-heptanedione (Problem 23-51) has two singlet absorptions in the 1H NMR spectrum, at 1.65 d and 1.90 d, and has no absorptions in the range 3 to 10 d. What is its structure?
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