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Chapter 22: Q.69P-A (page 1204)

Question: Predict the products of the following reactions

a. Cyclopentanone +Br2 in acetic acid

Short Answer

Expert verified

Answer

Step by step solution

01

Acid catalyst alpha halogenation

It is a reaction shown by an enolate ion formed by aldehyde or ketone in which halogenation occurs at the alpha position to the carbonyl.

02

Reaction of Cyclopentanone + in acetic acid

Cyclopentanone forms the enolate ion on reaction with the acetic acid, followed by the halogenation at the alpha position to the carbonyl of cyclopentanone as shown:

03

Mechanism

  1. Carbonyl is protonated with acetic acid
  2. Formation of the enolate ion
  3. Alpha halogenation

Mechanism

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Most popular questions from this chapter

Question:Show how you would use the Robinson annulation to synthesize the following compounds.

C.

Show how an acetoacetic ester synthesis might be used to form a 未 -diketone such as heptane-2,6-dione.

For each molecule shown below,

  1. Indicate the most acidic hydrogens.
  2. Draw the important resonance contributors of the anion that results from removal of the most acidic hydrogen.

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

e.

Show how you would use the malonic ester synthesis to make the following compounds
See all solutions

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