a) Interpretation: The preparation of the compound shown using acetoacetic ester synthesis is to be given. 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 primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S N 2 attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation. To give: The preparation of the compound shown using acetoacetic ester synthesis.

Question

Nitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

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 primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

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 primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

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