Skip to main content
Pearson+ LogoPearson+ Logo
Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 14, Problem 15b

Draw the condensed structural formula for the ester formed when each of the following reacts with methyl alcohol: 
b. pentanoic acid

Verified step by step guidance
1
Identify the functional groups involved in the reaction: Pentanoic acid contains a carboxylic acid group (-COOH), and methyl alcohol contains a hydroxyl group (-OH). The reaction between these two will form an ester through a condensation reaction.
Understand the esterification process: In esterification, the hydroxyl group (-OH) from the carboxylic acid reacts with the hydrogen atom from the alcohol's hydroxyl group (-OH), releasing a molecule of water (H₂O). The remaining parts combine to form the ester bond (-COO-).
Determine the structure of pentanoic acid: Pentanoic acid has a five-carbon chain with the carboxylic acid group (-COOH) attached to the first carbon. Its condensed structural formula is CH₃(CH₂)₃COOH.
Combine the alcohol and acid: Methyl alcohol (CH₃OH) contributes the methyl group (-CH₃) to the ester. Replace the hydrogen atom of the carboxylic acid's hydroxyl group (-OH) with the methyl group (-CH₃) from methyl alcohol.
Write the condensed structural formula for the ester: The ester formed will have the structure CH₃(CH₂)₃COOCH₃, where the -COO- group connects the pentanoic acid chain to the methyl group from methyl alcohol.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2m
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Esterification Reaction

Esterification is a chemical reaction between an alcohol and a carboxylic acid, resulting in the formation of an ester and water. In this process, the hydroxyl group (-OH) from the acid and a hydrogen atom from the alcohol combine to release water, while the remaining parts form the ester. Understanding this reaction is crucial for predicting the structure of the resulting ester.
Recommended video:
Guided course
0:46
Ester Reactions: Esterification Example 1

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms in a molecule without depicting all the bonds explicitly. It provides a simplified view of the molecular structure, indicating how atoms are grouped together. This format is particularly useful for visualizing organic compounds like esters, where functional groups play a significant role.
Recommended video:
Guided course
1:53
Condensed Formula Concept 1

Pentanoic Acid

Pentanoic acid, also known as valeric acid, is a five-carbon straight-chain carboxylic acid with the formula C5H10O2. It features a carboxyl group (-COOH) at one end of the carbon chain, which is essential for its reactivity in esterification. Recognizing the structure of pentanoic acid is vital for accurately drawing the condensed structural formula of the ester formed when it reacts with methyl alcohol.
Recommended video: