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Chapter 21: Q-21-21-6P (page 688)

The following structure represents a tetrahedral alkoxide ion intermediate formed by the addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product.

Short Answer

Expert verified

The nucleophile is OH-.

The leaving group in the molecule is CH3O-. The derivative of starting acid is methyl-2-cyclopentylacetate.

The ultimate products are methanol and cyclopentylacetate anion.

Step by step solution

01

The given species

The representation of alkaline ion using the model as below:

02

The nucleophilic substitution reaction

In the given reaction, the reacting molecule is shown below:

The nucleophilic attack by the base () hydroxide ion can yield the intermediate. This will lose a methoxyl group and yields 2-cyclopentyl-1-hydroxy-1-methoxyethan-1-olate as the intermediate. Then the leaving group that is acetate leaves the substrate molecule and forms the respective products.

03

Explanation

The nucleophile is .

The leaving group in the molecule is . The derivative of starting acid is methyl-2-cyclopentylacetate.

The ultimate products are methanol and cyclopentylacetate anion.

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Most popular questions from this chapter

21-68 When a carboxylic acid is dissolved in isotopically labeled water, thelabel rapidly becomes incorporated into both oxygen atoms of the carboxylic acid. Explain.
R鈭�C鈭�O鈭�OH鈫�H2OR鈭�C鈭�O鈭�OH

How would you prepare the following compounds starting with an appropriate carboxylic acid and any other reagents needed? (Reddish brown = Br.)

a.

b.

Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step:

Show the products you would obtain by reduction of the following esters with LiAlH4:

(a) (b)

21-47 Draw and name compounds that meet the following descriptions:
(a) Three acid chlorides having the formulaC6H9ClO
(b) Three amides having the formula C7H11NO
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