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Chapter 23: Q42. (page 924)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

The stepwise mechanism of the haloform reaction is shown below.

Step by step solution

01

Haloform reaction

Halogenation is carried out by treating a carbonyl compound with alpha hydrogen atoms with a halogen in the presence of a base. When excess halogens are present, all the possible acidic protons get replaced by halogens. This reaction is known as the haloform reaction.

02

Mechanism involved in the haloform reaction

The first step is the abstraction of a base. The second step is the formation of an enolate, followed by the third step that is the attack of an electrophile in the presence of a base.

Representation of the stepwise reaction scheme of the haloform reaction.

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Most popular questions from this chapter

Question: A key step in the synthesis of the narcotic analgesic meperidine (trade name Demerol) is the conversion of phenyl acetonitrile to X. (a) What is the structure of X? (b) What reactions convert X to meperidine?

Question: Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen.

a. Write out a synthesis of nabumetone from ethyl acetoacetate.

b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?

Question: (–)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer isolated from the tailflower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.

Question: As we learned in Chapter 20, organolithium reagents (RLi) are strong bases that readily react with acidic protons. Why aren’t organolithium reagents used to generate enolates?

Question: Treatment of W with CH3Li, followed by CH3l, affords compound Y (C7H14O ) as the major product. Y shows a strong absorption in its IR spectrum at , and its 1 H NMR spectrum is given below. (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.
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