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Chapter 23: Q62. (page 924)

Question:

(a) Draw two different haloketones that can form A by an intramolecular alkylation reaction.

(b) How can A be synthesized by an acetoacetic ester synthesis?

Short Answer

Expert verified

Answer

(a)


(b)

Step by step solution

01

Generation of an enolate

The reaction of a carbonyl compound with a base generates an enolate (carbanion is generated at the alpha carbon).

02

Haloketones involved in the synthesis of A

The compound A can be synthesized using the given haloketones.

The reaction of the haloketones in the presence of a base yielding compound A is shown below.

Haloketones used in the synthesis of A

03

Synthesis of A by acetoacetic ester synthesis

The reaction of the given substituted acetoacetic ester with base generates an enolate.

The enolate attacks the electron-deficient carbon atom (the carbon atom attached to the electronegative bromine atom).

The basic hydrolysis of the obtained product yields compound A.

Synthesis of A by acetoacetic ester synthesis

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Most popular questions from this chapter

Question: The cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.

Question: Draw a stepwise mechanism for the following reaction.

Question: When phenylacetaldehyde (C6H5CH2CHO) is dissolved in with added DCl, the hydrogen atomsαto the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.

Question: What alkyl halides are needed to prepare each ketone using the acetoacetic ester synthesis?

Question: Explain why pentane-2,4-dione forms two different alkylation products (A or B) when the number of equivalents of base is increased from one to two.
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