a) Interpretation: The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated. Concept introduction: Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation. To state: The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Question

1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

Answer 1

Question

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

Concept introduction:Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

concept introduction: Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

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