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Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 14th Edition
Timberlake14thChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook
Chapter 14, Problem 73b

Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following:
b. Condensed structural formula showing amide hydrolysis with sodium hydroxide and heat.

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1
Identify the type of hydrolysis reaction: Hydrolysis typically involves breaking a bond in a molecule using water. In this case, the reaction likely involves an ester or amide bond, as these are common in hydrolysis reactions.
Determine the functional group in the given compound: Examine the structure in the image to identify whether it contains an ester or amide group. These groups are cleaved during hydrolysis to form specific products.
Write the general reaction for hydrolysis: For an ester, hydrolysis produces a carboxylic acid and an alcohol. For an amide, hydrolysis produces a carboxylic acid and an amine. Represent this reaction using condensed structural formulas or line-angle formulas.
Break the molecule at the hydrolyzable bond: Using the structure provided in the image, locate the bond between the carbonyl carbon and the oxygen (for esters) or the nitrogen (for amides). Split the molecule at this bond and add the components of water (H and OH) to the resulting fragments.
Draw the products: Represent the resulting carboxylic acid and alcohol (or amine) using condensed structural formulas or line-angle formulas. Ensure that the structures are complete and correctly show the addition of H and OH from water.

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Key Concepts

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

Hydrolysis

Hydrolysis is a chemical reaction in which water is used to break down a compound. In organic chemistry, it often involves the cleavage of bonds in larger molecules, such as esters or amides, resulting in the formation of smaller molecules, typically an acid and an alcohol or amine. Understanding hydrolysis is crucial for predicting the products formed from the reaction.
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Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. It provides a simplified view of the molecule, making it easier to visualize the structure and functional groups present. This format is particularly useful for larger organic molecules.
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Line-Angle Formula

The line-angle formula, also known as the skeletal formula, is a shorthand representation of organic molecules where vertices represent carbon atoms and lines represent bonds. This method omits hydrogen atoms attached to carbons, simplifying the structure for easier interpretation. It is widely used in organic chemistry to depict complex molecules clearly and efficiently.
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