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 45b

Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with HCl:
b. Condensed structural formula of an amide featuring a carbonyl group and an amine group.

Verified step by step guidance
1
Identify the functional group in the given compound. In this case, the compound is an amide, which contains a carbonyl group (C=O) directly bonded to a nitrogen atom (N).
Understand the reaction type: Hydrolysis of an amide in the presence of HCl involves breaking the bond between the carbonyl carbon and the nitrogen atom. This reaction produces a carboxylic acid and an ammonium salt.
Determine the products: The carbonyl carbon will form a carboxylic acid group (-COOH), while the nitrogen atom will bond with a hydrogen ion (H⁺) from HCl to form an ammonium ion (R-NH₃⁺).
Draw the condensed structural formula or line-angle formula for the carboxylic acid product. Replace the amide group with a carboxylic acid group (-COOH) in the structure.
Draw the condensed structural formula or line-angle formula for the ammonium salt product. The nitrogen atom from the amide will now be part of an ammonium ion (R-NH₃⁺), paired with a chloride ion (Cl⁻) from HCl.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
42s
Was this helpful?

Key Concepts

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

Hydrolysis of Amides

Hydrolysis of amides involves the reaction of an amide with water, often in the presence of an acid or base, to produce a carboxylic acid and an amine or ammonia. In this case, hydrochloric acid (HCl) acts as the catalyst, facilitating the breakdown of the amide bond. Understanding this process is crucial for predicting the products formed during the reaction.
Recommended video:
Guided course
1:12
Acidic Hydrolysis Concept 1

Condensed Structural Formula

A condensed structural formula provides a simplified representation of a molecule, showing the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. This format is useful for quickly conveying the structure of organic compounds, especially in complex molecules, making it easier to visualize the products of chemical reactions.
Recommended video:
Guided course
1:53
Condensed Formula Concept 1

Line-Angle Formula

The line-angle formula, also known as the skeletal formula, is a shorthand way of drawing organic molecules where vertices represent carbon atoms and lines represent bonds. This method simplifies the representation of larger molecules by omitting hydrogen atoms attached to carbons, allowing for a clearer view of the molecular structure and functional groups, which is essential for understanding the products of hydrolysis.
Recommended video:
Guided course
01:24
Bond Angles (Simplified) Concept 1