Monocarboxylic Acids: Structure, Properties & Uses

Lesson Transcript
Instructor: Sarah Pierce

Sarah has a doctorate in chemistry, and 12 years of experience teaching high school chemistry & biology, as well as college level chemistry.

This lesson covers the structure and properties of monocarboxylic acids. The preparation of monocarboxylic acids from alcohols, nitriles, and acyl chlorides is discussed. Practical uses of carboxylic acids as medicine and soap are also covered. Updated: 09/21/2022

What Is Monocarboxylic Acid?

Imagine you're biting into a juicy hamburger and crunch into a pickle. The tell-tale taste of vinegar fills your mouth. Have you ever wondered what vinegar actually is? The scientific name for vinegar is acetic acid, and the molecule is a monocarboxylic acid.

A carboxylic acid is an organic molecule that has mostly carbon and hydrogen atoms but also contains a carbon that has a double bond to an oxygen. The carbon that's doubly bound to the oxygen is attached to another oxygen, which is bound to a hydrogen. This functional group is the part of the molecule that changes in chemical reactions and is sometimes shown as -COOH or CO2 H.

Molecules can have several carboxylic acid functional groups. Citric acid, the carboxylic acids that adds a citrus taste to your soda, has three carboxylic acid groups. When a molecule has just has one carboxylic acid group, it's defined as a monocarboxylic acid.

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  • 0:04 What Is Monocarboxylic Acid?
  • 1:04 Properties
  • 1:59 Synthesis
  • 3:09 Uses
  • 3:48 Lesson Summary
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Properties

Carboxylic acids are weak acids. This means that the COOH group gives its proton to another chemical, or is deprotonated. When the COOH loses an H, a carboxylate ion (COO-) forms. Acids have sour tastes, which is why citric acid is added to candy to give it a slightly sour taste.

The solubility of carboxylic acid molecules depends on the number of carbon atoms in the entire molecule. If the molecule has fewer than five carbons, it's soluble in water. If the molecule has more than five carbons, it is not soluble in water.

Carboxylic acid molecules tend to form hydrogen bonds with each other in solution. They form dimers, or two molecules that are associated with each other. Because it takes so much energy to break these bonds, the boiling point of carboxylic acids is greater than water.

Synthesis

Carboxylic acids can be synthesized in many ways. These are generally used in organic chemistry synthesis and teaching laboratories. If you have taken a chemistry lab, you may have synthesized a carboxylic acid. Let's look at three ways we can make carboxylic acids.

1. Oxidation of Alcohols

A primary alcohol can react with an oxidizer to produce carboxylic acids. Primary alcohols are OH groups attached to a carbon with two hydrogens. A common chemical that can oxidize alcohols is chromic acid (H2 CrO4).

2. Hydration of Nitriles

Nitriles are molecules with a carbon that has a triple bond to a nitrogen. A nitrile can react with an acid and water to form carboxylic acids. Whenever water reacts with a compound, the process is called hydration, or hydrolysis.

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