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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 79d

Propyl acetate is the ester that gives the odor and smell of pears.
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d. Write the balanced chemical equation for the base hydrolysis of propyl acetate with NaOH.

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1
Identify the reactants: Propyl acetate (C3H7COOCH3) and sodium hydroxide (NaOH). Base hydrolysis of an ester involves breaking the ester bond in the presence of a strong base like NaOH.
Understand the reaction mechanism: In base hydrolysis (saponification), the ester reacts with the hydroxide ion (OH⁻) from NaOH. This breaks the ester bond, forming a carboxylate salt and an alcohol.
Write the general reaction format: RCOOR' + NaOH → RCOONa + R'OH. Here, R is the propyl group (C3H7), and R' is the methyl group (CH3).
Substitute the specific groups into the general reaction: C3H7COOCH3 + NaOH → C3H7COONa + CH3OH.
Verify the equation is balanced: Ensure the number of each type of atom is the same on both sides of the equation. In this case, the equation is already balanced as written.

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Key Concepts

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

Ester Hydrolysis

Ester hydrolysis is a chemical reaction where an ester reacts with water to form an alcohol and a carboxylic acid. In the case of propyl acetate, hydrolysis involves breaking the ester bond in the presence of water, leading to the formation of propanol and acetic acid. This reaction can occur under acidic or basic conditions, with base hydrolysis often referred to as saponification.
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Balanced Chemical Equation

A balanced chemical equation represents a chemical reaction with equal numbers of each type of atom on both sides of the equation. Balancing is essential to obey the law of conservation of mass, which states that matter cannot be created or destroyed in a chemical reaction. For the hydrolysis of propyl acetate, the equation must reflect the reactants (propyl acetate and sodium hydroxide) and the products (propanol and acetic acid) in stoichiometric proportions.
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Saponification Reaction

Saponification is a specific type of ester hydrolysis that occurs in the presence of a strong base, such as sodium hydroxide (NaOH). This reaction is commonly associated with the production of soap from fats and oils, but it also applies to esters like propyl acetate. During saponification, the ester is converted into an alcohol and a carboxylate salt, which is the basis for soap formation.
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