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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 27a

Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:
a. Condensed structural formula of an ester reacting with sodium hydroxide under heat, indicating saponification.

Verified step by step guidance
1
Understand the concept of hydrolysis: Hydrolysis is a chemical reaction where a water molecule breaks a bond in a compound. In acid- or base-catalyzed hydrolysis, the reaction is facilitated by an acid (H⁺) or a base (OH⁻). For esters, hydrolysis typically results in the formation of a carboxylic acid and an alcohol.
Analyze the given compound: Since the problem references an image, identify the functional group in the compound (e.g., ester, amide, etc.) and its structure. For an ester, the general formula is RCOOR', where R and R' are alkyl or aryl groups.
Determine the products of hydrolysis: In acid-catalyzed hydrolysis of an ester, the ester reacts with water in the presence of an acid to produce a carboxylic acid (RCOOH) and an alcohol (R'OH). In base-catalyzed hydrolysis (saponification), the ester reacts with a base (e.g., NaOH) to produce a carboxylate salt (RCOO⁻Na⁺) and an alcohol (R'OH).
Draw the condensed structural formulas: For the acid-catalyzed hydrolysis, write the condensed structural formulas for the carboxylic acid and alcohol. For the base-catalyzed hydrolysis, write the condensed structural formulas for the carboxylate salt and alcohol.
Draw the line-angle formulas: Convert the condensed structural formulas into line-angle formulas, which are simplified representations where bonds between carbon atoms are shown as lines, and hydrogen atoms are typically omitted for clarity.

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Key Concepts

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

Acid-Base Catalysis

Acid-base catalysis involves the acceleration of a chemical reaction by the presence of an acid or a base. In hydrolysis reactions, acids can donate protons to facilitate the breaking of bonds, while bases can accept protons to stabilize intermediates. Understanding this concept is crucial for predicting the products formed during hydrolysis.
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Hydrolysis

Hydrolysis is a chemical reaction in which water is used to break down a compound. In organic chemistry, this often involves the cleavage of bonds in larger molecules, resulting in the formation of smaller products. Recognizing the type of hydrolysis (acidic or basic) is essential for determining the resulting structures.
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Condensed Structural and Line-Angle Formulas

Condensed structural formulas provide a shorthand way to represent the structure of a molecule, showing how atoms are connected without depicting all bonds explicitly. Line-angle formulas, on the other hand, use lines to represent bonds and vertices to represent carbon atoms, simplifying the visualization of complex organic structures. Mastery of these representations is vital for accurately illustrating the products of hydrolysis.
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