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Chapter 22: 54E (page 752)

Fill in the reagents a鈥揷 that are missing from the following scheme:

Short Answer

Expert verified

The reagents are:

(a) NaOC2H5/CH3I

(b) H3O+/Heat ,and

(c) LDA/CH3I.

Step by step solution

01

  Acidic hydrogens in ketones

The alpha hydrogens in ketones are acidic in nature. The acidic protons will be removed in reaction with a strong base, and a carbanion intermediate will be formed. This carbanion intermediate on reaction with an alkyl halide forms a new C-C bond.

The given reaction is,

The given equation

02

Reagents

The reagents used in the reaction are,

The given chemical reaction

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Most popular questions from this chapter

If methanol rather than water is added at the end of a Hell鈥揤olhard鈥揨elinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.


The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.

How would you prepare the following compounds using either an Acetoacetic ester synthesis or a malonic ester synthesis?

Although 2-substituted 2-cyclopentenones are in a base-catalyzed equilibrium with their 5-substituted 2-cyclopentenone isomers (Problem 22-55), the analogous isomerization is not observed for 2-substituted 2-cyclohexenones. Explain.

Amino acids can also be prepared by a two-step sequence that involves Hell鈥揤olhard鈥揨elinskii reaction of a carboxylic acid followed by treatment with ammonia. Show how you would prepare leucine, (CH3)2CHCH2CH(NH2)CO2H, and identify the mechanism of the second step.
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