Textbook Question
Predict the product of the following reactions.
(a)
22. Carboxylic Acid Derivatives: NAS
Carboxylic Acid to Acid Chloride
5:30 minutesProblem 72c
Textbook Question
How could you convert N-methylbenzamide to the following compounds?
c. methyl benzoate
Verified step by step guidance1
Step 1: Recognize that N-methylbenzamide is an amide, and methyl benzoate is an ester. The conversion involves replacing the amide group (-CONHCH3) with an ester group (-COOCH3). This typically requires hydrolysis followed by esterification.
Step 2: Perform acidic or basic hydrolysis of N-methylbenzamide to break the amide bond. This will yield benzoic acid (C6H5COOH) and methylamine (CH3NH2). Use a strong acid like HCl or a strong base like NaOH for this step.
Step 3: Isolate the benzoic acid from the reaction mixture. If basic hydrolysis was used, acidify the solution to precipitate benzoic acid.
Step 4: React the benzoic acid with methanol (CH3OH) in the presence of an acid catalyst, such as sulfuric acid (H2SO4), to perform esterification. This will convert benzoic acid into methyl benzoate.
Step 5: Purify the methyl benzoate product using techniques such as distillation or recrystallization, depending on the reaction conditions and impurities.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amide Hydrolysis
Amide hydrolysis is a reaction where an amide is converted into a carboxylic acid and an amine or ammonia, typically in the presence of water and an acid or base. This reaction is crucial for understanding how to transform N-methylbenzamide into its corresponding carboxylic acid, which can then be further converted into methyl benzoate.
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Esterification
Esterification is the process of forming an ester from a carboxylic acid and an alcohol, usually in the presence of an acid catalyst. In this case, the carboxylic acid derived from the hydrolysis of N-methylbenzamide can react with methanol to produce methyl benzoate, illustrating the importance of this reaction in organic synthesis.
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Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. This mechanism is key in the conversion of the carboxylic acid formed from N-methylbenzamide into the ester methyl benzoate, as the alcohol acts as the nucleophile.
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