Carboxylic Acids and Their Derivatives Practice Problems

Carboxylic acid derivatives practice problems

This is a comprehensive practice problem covering most of the nucleophilic acyl substitution reactions of carboxylic acids and their derivatives.

Here is the content of this 1-hour video for the practice problem solutions:

The detailed mechanism for reactions such as Fischer esterification, ester hydrolysis, transesterification, the reaction of carboxylic acids with amines to produce salts, and using a coupling agent or converting them first to acyl chlorides using thionyl chlorides to prepare amides.

The mechanisms of acid or base-catalyzed hydrolysis of amides, imines, nitriles, and esters. The similarity and difference of the Grignard and Organocuprates reactions with esters, acid chlorides, anhydrides, and nitriles, and their mechanisms.

You can also find all of these reactions in one powerful summary sheet, which is part of the Organic 1 and 2 Summary guides and included in CS memberships.

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

This beautiful Summary Guide includes the Nucleophilic Acyl Substitution mechanism, also referred to as an Addition-Elimination mechanism, the mechanism of Fischer esterification.

The reaction of esters, such as reversible hydrolysis under acidic and irreversible hydrolysis under basic conditions, transesterification, and all the others with nucleophiles and reducing agents.

You will have a comprehensive summary of the preparation and all the major reactions of Carboxylic Acids, Anhydrides, Esters, Acid (acyl) Chlorides, Amides, and Nitriles. All the common patterns, as well as the details for specific reactions, for example, with the Grignard reagent and Organocuprates of each derivative, are addressed in the given section.

Attempt to solve each problem before checking the answer and solution.

Here is also a 45-question, Multiple-Choice Quiz with a 50-minute Video Solution on the reactions of carboxylic acids and their derivatives. 

Free

Carboxylic Acids and Their Derivatives Quiz

Reactions of Carboxylic Acids and Their Derivatives

📥 Download this Study Guide of Carboxylic Acid Derivatives and others here.

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

🗺️ All the Conversions of Carboxylic Acid Derivatives in a Comprehensive Reaction Map

 

Practice

1.

Predict the major product for each nucleophilic acyl substitution reaction and draw the corresponding curved-arrow mechanism:

a)
Answer

This is a Fischer esterification.

Check the video under the “Solution” tab for the mechanism.

b)
Answer
c)
Answer

Without a coupling reagent, the carboxylic acid and amine react as acid and base.

d)
Answer
e)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

f)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

g)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

h)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

i)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

j)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

k)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

l)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

m)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

n)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

o)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

p)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

q)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

r)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

s)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

t)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

u)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

v)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

w)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

x)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

y)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

z)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

Solution

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

2.

Propose reagents for reducing the following carbonyl compounds:

a)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

b)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

c)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

d)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

e)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

f)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

g)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

3.

Predict the major organic product(s) for each of the following reactions. They all involve carboxylic acid derivatives such as esters, acid chlorides, nitriles, anhydrides, and amides. You may also need to go over the reactions covered in earlier chapters, particularly, the Grignard and Gilman reagents, oxidizing and reducing agents, and electrophilic aromatic substitutions.

A link to each topic encountered in a given problem will be provided in the answer tab.

 

a)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

b)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

c)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

d)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

e)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

;

f)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

g)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

h)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

i)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

j)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

k)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

l)
Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

4.

Add the missing reagent in the following synthetic scheme on carboxylic acid derivatives:

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

5.

Draw a plausible mechanism for the following synthetic transformation:

 

 

 

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

 

6.

Propose a mechanism for the following synthetic transformation:

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

 

7.

Friedel-Crafts acylation of carboxylic acids is not very common as the carbonyl group is not so electrophilic. One of the ways to activate the acid is the use of TFAA (Trifluoroacetic anhydride). Propose a mechanism for the following Friedel-Crafts acylation and explain the role of TFAA:

 

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

8.

Propose a mechanism for the following Friedel-Crafts acylation reaction.

 

 

Note: H3O+ with heat is used for hydrolyzing the ester into a carboxylic acid. 

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

9.

Chemiluminescence is used for many applications including glow sticks. The principle behind this process is the excitation of fluorescent dyes such as rhodamines, perylenes, anthracenes, and many more using a chemical reaction. In other words, the source of energy for the excitation of the dye is a chemical reaction. Most often the energy is generated as a result of spontaneously decomposing carbon dioxide dimer which, in turn, is produced via the oxidation of diaryl oxalate diesters with hydrogen peroxide:

 

 

Draw a curved arrow mechanism for the formation of the carbon dioxide dimer and explain why perylene is aromatic despite having 20 π electrons.

 

 

Answer

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.

10.

Check Also

Share Your Thoughts, Ask that Question!