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Chapter 5: Problem 95

The product formed by the reaction of ethyl acetate with sodium ethoxide is (a) ethyl acetoacetate (b) ethyl propionate (c) Propane-2, 3-dione (d) 3-oxobutanal

Short Answer

Expert verified
Answer: The product formed in the reaction between ethyl acetate and sodium ethoxide is ethyl acetoacetate.

Step by step solution

01

Identify the reactants

The reactants in this exercise are ethyl acetate (CH3-COO-CH2-CH3) and sodium ethoxide (CH3-CH2-O-Na). Ethyl acetate is an ester and sodium ethoxide is an alkoxide salt.
02

Understand the reactivity of esters

Esters (R-COO-R') can undergo nucleophilic substitution reactions. In this type of reaction, the nucleophile (a species with a lone pair of electrons) attacks the carbonyl group (C=O), breaking the C-O bond in the process and eventually resulting in the formation of a new C-O bond and releasing a leaving group.
03

Determine the nucleophilic attack site

In this reaction, sodium ethoxide (CH3-CH2-O-Na) acts as the nucleophile. The oxygen atom in the ethoxide ion has a lone pair of electrons that can attack the carbonyl carbon in ethyl acetate. This results in cleavage of the C-O bond and displacement of the leaving group (ethoxide ion).
04

Write the product after nucleophilic attack

The nucleophilic attack by the ethoxide ion on the carbonyl carbon will create a new C-O bond, resulting in the formation of the product ethyl acetoacetate: CH3-C(O)-CH2-C(O)-O-CH2-CH3. The sodium ion will retain its positive charge and be present as a counterion.
05

Identify the correct answer

The correct answer is option (a) ethyl acetoacetate, as this is the product formed after the nucleophilic substitution reaction between ethyl acetate and sodium ethoxide.

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Most popular questions from this chapter

Which of the following statements relating to the derivatives of carboxylic acids are correct? (a) An amide \(\mathrm{R}-\mathrm{C}\), answers all the tests for a primary amine. (b) Esters undergo hydrolysis more readily than acid amides.. (c) Carboxylic acid can be converted to an ester by reacting with alcohol in the presence of a base (d) Benzoic acid can be converted to methyl benzoate by using diazomethane.

Identify the product (c) in the following sequence of reaction \(\mathrm{PhCH}_{2} \mathrm{Cl} \underset{\text { DMF }}{\longrightarrow}(\mathrm{A}) \stackrel{\mathrm{KCN}}{\text { PhCHO/A }}\) (B) \(\stackrel{\mathrm{H}_{3} \mathrm{O}^{+}}{\longrightarrow}(\mathrm{C})\)

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An organic compound \((X)\) when heated with concentrated \(\mathrm{NaOH}\) solution followed by acidification gave the following O=C1OCc2ccccc21 lactone as the only organic product The compound \((\mathrm{X})\) is (a) O=Cc1ccccc1C=O (b) O=Cc1ccccc1C(=O)O (c) CCOC(=O)c1ccccc1C(=O)O (d) O=C(O)c1ccccc1C(=O)O

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