Organic Chemistry : Help with Carboxylic Acid Reactions

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Help With Carboxylic Acid Reactions

Screen shot 2015 07 19 at 11.39.38 am

Which reagent may be used to convert a carboxylic acid to an acid chloride, as shown?

Possible Answers:

Correct answer:

Explanation:

It is extremely useful in organic synthesis to utilize methods by which less reactive carboxylic acids (and their derivatives) may be converted to more reactive species, like acid chlorides. Such reactions are not always intuitive as they proceed by transforming low-energy species to more energetic states. Reagents such as thionyl chloride  and phosphorus tribromide , which you have likely seen previously in examination of common alcohol reactions, readily convert carboxylic acids to acid chlorides. The reaction is energetically favorable due to the formation of sulfur dioxide, a very stable gas.

Example Question #13 : Carbonyl Reactants

Which of the following is derived from a carboxylic acid?

Possible Answers:

None of these

Aldehyde

Imine

Acid anhydride

Correct answer:

Acid anhydride

Explanation:

A carboxylic acid can be synthesized directly into an acid anhydride by introducing the carboxylic acid to an acid chloride.

Example Question #2 : Help With Carboxylic Acid Reactions

Socl2 reactant

What is the major product of the given reaction?

Possible Answers:

Socl2 correct product

Socl2 incorrect product 3

Socl2 incorrect product 2

Socl2 incorrect product

Correct answer:

Socl2 correct product

Explanation:

This question is asking us to determine what the product will be when a carboxylic acid is reacted with thionyl chloride, . In this reaction, the carboxylic acid is converted into an acyl chloride, with additional production of  and  as side products. Generally, this reaction is very useful for converting carboxylic acids into a more reactive form, so that further reactions can take place.

Example Question #52 : Reactions By Reactant

What is the product of the reaction shown?

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Screen shot 2015 11 13 at 1.40.10 pm

Possible Answers:

II

I

III

IV

Correct answer:

III

Explanation:

The Grignard reagent also acts as a base, and will remove any protons that have a low-enough pKa. This means that the alpha hydrogen will be removed, and the resulting carboxylate ion is stabilized through resonance and is unlikely to react with the protonated Grignard reagent.

Example Question #3 : Help With Carboxylic Acid Reactions

What is the product of the reaction below?

Image12

Possible Answers:

Correct answer:

Explanation:

This reaction is an acid-catalyzed esterification of a carboxylic acid. In the reaction the carbonyl is attacked by the alcohol oxygen, and the carbonyl is reformed by kicking off what was the hydroxyl group in the original carboxylic acid. What is left is an ester (of the form RCOOR', with R' containing the same number of carbons as was in the original alcohol).

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