Ch. 21 - Carboxylic Acid Derivatives

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch. 21 - Carboxylic Acid Derivatives

Problem 47a

Chapter 21, Problem 47a

Predict the products of saponification of the following esters.
(a)

Verified step by step guidance

Step 1: Understand the concept of saponification. Saponification is the base-catalyzed hydrolysis of an ester, resulting in the formation of a carboxylate salt and an alcohol. The reaction typically involves a strong base like NaOH or KOH.

Step 2: Analyze the given ester structure. The ester provided is phenyl formate (HCOOPh), where the ester functional group consists of a formyl group (HCO-) and a phenyl group (Ph).

Step 3: Write the general reaction for saponification. The ester reacts with a strong base (e.g., NaOH) to produce a carboxylate salt and an alcohol. In this case, the formyl group will form a formate ion (HCOO⁻), and the phenyl group will form phenol (C₆H₅OH).

Step 4: Break down the reaction mechanism. The hydroxide ion (OH⁻) attacks the carbonyl carbon of the ester, leading to the cleavage of the ester bond. This results in the formation of the carboxylate ion and the alcohol.

Step 5: Summarize the products. The saponification of phenyl formate will yield sodium formate (HCOONa, if NaOH is used) and phenol (C₆H₅OH) as the final products.

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Key Concepts

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

Saponification

Saponification is a chemical reaction that involves the hydrolysis of esters in the presence of a strong base, typically sodium hydroxide (NaOH) or potassium hydroxide (KOH). This process breaks the ester bond, resulting in the formation of an alcohol and a carboxylic acid salt, commonly known as soap. Understanding this reaction is crucial for predicting the products when esters undergo saponification.

Esters

Esters are organic compounds formed from the reaction of an alcohol and a carboxylic acid, characterized by the functional group -COO-. They are often responsible for the pleasant aromas of fruits and flowers. In the context of saponification, recognizing the structure of the ester, including the alkyl and aryl groups, is essential for determining the resulting products after the reaction.

Hydrolysis

Hydrolysis is a chemical process in which water is used to break down a compound. In the case of saponification, hydrolysis refers to the reaction of the ester with water, facilitated by a base, leading to the formation of an alcohol and a carboxylic acid. Understanding hydrolysis is key to predicting the products of saponification, as it directly relates to how the ester is converted into its constituent parts.

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Related Practice

Textbook Question

Predict the products of the following reactions.

(e)

(f)

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Textbook Question

Predict the products of saponification of the following esters.

(b)

915

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Textbook Question

Acid-catalyzed transesterification and Fischer esterification take place by nearly identical mechanisms. Transesterification can also take place by a base-catalyzed mechanism, but all attempts at base-catalyzed Fischer esterification (using –OR″, for example) seem doomed to failure. Explain why Fischer esterification cannot be catalyzed by base.

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Textbook Question

Predict the products of saponification of the following esters.

(d)

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Textbook Question

Predict the products of saponification of the following esters.

(c)

847

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