Textbook Question
How would you make the following compounds from N-benzylbenzamide?
b. benzoic acid
22. Carboxylic Acid Derivatives: NAS
Acid-Catalyzed Ester Hydrolysis
6:41 minutesProblem 17a
Textbook Question
Write a mechanism for each of the following reactions:
a. the uncatalyzed hydrolysis of methyl propionate.
Verified step by step guidance1
Identify the functional group in methyl propionate. Methyl propionate is an ester, which has the general structure RCOOR'. The hydrolysis of an ester involves breaking the ester bond to form a carboxylic acid and an alcohol.
Understand the reaction conditions. Since the problem specifies 'uncatalyzed hydrolysis,' the reaction will proceed without the aid of an acid or base catalyst. This means the reaction will rely on water as the nucleophile and proceed more slowly.
Initiate the mechanism. The lone pair of electrons on the oxygen atom in a water molecule attacks the carbonyl carbon of the ester group. This is a nucleophilic addition step. Represent this step as: .
Form the tetrahedral intermediate. After the nucleophilic attack, the carbonyl carbon becomes sp³ hybridized, and a tetrahedral intermediate is formed. This intermediate contains a hydroxyl group (-OH) and the original alkoxy group (-OR') attached to the same carbon.
Complete the reaction. The tetrahedral intermediate undergoes a rearrangement where the alkoxy group (-OR') is eliminated, leading to the formation of a carboxylic acid (RCOOH) and an alcohol (R'OH). This step regenerates the carbonyl group in the carboxylic acid.
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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 involving the breaking of a bond in a molecule using water. In organic chemistry, it often refers to the reaction of esters or amides with water, leading to the formation of an alcohol and a carboxylic acid. Understanding hydrolysis is crucial for analyzing reactions involving esters, such as methyl propionate, as it dictates the pathway and products formed.
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Mechanism of Reaction
A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the individual steps, intermediates, and transition states involved in the reaction. For the uncatalyzed hydrolysis of methyl propionate, detailing the mechanism helps in understanding how water interacts with the ester bond and the subsequent formation of acetic acid and methanol.
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Esters and Their Reactivity
Esters are organic compounds formed from the reaction of an alcohol and a carboxylic acid, characterized by the functional group -COO-. They are generally reactive towards nucleophiles, such as water in hydrolysis reactions. Recognizing the structure and reactivity of esters like methyl propionate is essential for predicting the outcome of hydrolysis and understanding the role of the ester functional group in organic reactions.
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