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22. Carboxylic Acid Derivatives: NAS

Fischer Esterification

22. Carboxylic Acid Derivatives: NAS

Fischer Esterification

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General Reaction

General Reaction

Johnny Betancourt

General Mechanism

General Mechanism

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Practice this topic

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Predict the esterification products of the following acid/alcohol pairs. (a) CH3CH2CH2COOH + CH3OH (b) CH3OH + HNO3 (c) 2CH3CH2OH + H3PO4

Textbook Question

When butanoic acid and 18^O-labeled methanol react under acidic conditions, what compounds are labeled when the reaction has reached equilibrium?

Textbook Question

a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethanol. Why? (HINT: Build models.) b. Would he have encountered the same problem if he had tried to synthesize the methyl ester of 4-methylbenzoic acid in the same way?

Textbook Question

Propose a mechanism for the following reaction. (HINT: Number the carbons to help you see where they end up in the product.)

Textbook Question

Show how each of the following esters could be prepared using a carboxylic acid as one of the starting materials: a. methyl butyrate (odor of apples)

Textbook Question

(b) Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.

Textbook Question

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion. (c) ethyl phenylacetate

Textbook Question

Show how you would accomplish the following syntheses in good yields. (c)

Textbook Question

Predict the esterification products of the following acid/alcohol pairs.

(d) <IMAGE of reaction>

(e) <IMAGE of reaction>

Textbook Question

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

Textbook Question

Suggest the most appropriate reagent for each synthesis, and explain your choice.

(b) <IMAGE>

Textbook Question

Show how you would convert alanine to the following derivatives. Show the structure of the product in each case. (a) alanine isopropyl ester (b) N-benzoylalanine

Textbook Question

Show how each of the following compounds can be prepared, using the given starting material: a.

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need. (f)

Textbook Question

Show the alcohol and the acid chloride that combine to make the following esters.

(c) <IMAGE>

(d) <IMAGE>

Textbook Question

The mechanism of the Fischer esterification was controversial until 1938, when Irving Roberts and Harold Urey of Columbia University used isotopic labeling to follow the alcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was added to a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy 18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction, and the components of the mixture were separated.

<IMAGE>

(a) Propose a mechanism for this reaction.

(b) Follow the labeled 18O atom through your mechanism, and show where it is found in the products.

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