Textbook Question
What acyl chloride and amine are required to synthesize the following amides?
a. N-ethylbutanamide
b. N,N-dimethylbenzamide
22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
5:27 minutesProblem 79
Textbook Question
Identify the major and minor products of the following reaction:
Verified step by step guidance1
Step 1: Analyze the reactants. The molecule contains two nucleophilic functional groups: a primary amine (-NH2) and a secondary amine (-NH). Both can react with the electrophilic acetyl chloride (CH3COCl). The hydroxyl group (-OH) is less nucleophilic and unlikely to react under these conditions.
Step 2: Consider the reaction conditions. Since only 1 equivalent of acetyl chloride is provided, only one nucleophilic site will react. The primary amine (-NH2) is more nucleophilic than the secondary amine (-NH) due to less steric hindrance and higher electron density.
Step 3: Predict the major product. The primary amine will likely react with acetyl chloride to form an amide bond. The reaction mechanism involves nucleophilic attack by the amine on the carbonyl carbon of acetyl chloride, followed by the elimination of HCl.
Step 4: Predict the minor product. If the secondary amine reacts instead, it will form a different amide product. However, this is less likely due to steric hindrance and the lower nucleophilicity of the secondary amine compared to the primary amine.
Step 5: Summarize the outcome. The major product will be the amide formed from the reaction of the primary amine with acetyl chloride. The minor product, if formed, would result from the reaction of the secondary amine with acetyl chloride.
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5mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks a carbonyl carbon, leading to the replacement of a leaving group. This reaction is characteristic of carboxylic acid derivatives, such as esters, amides, and acyl chlorides. Understanding this mechanism is crucial for predicting the major and minor products formed during the reaction.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Carboxylic Acid Derivatives
Carboxylic acid derivatives include compounds like acyl chlorides, esters, and amides, which can undergo nucleophilic acyl substitution. Each derivative has different reactivity due to the nature of the leaving group and the electrophilicity of the carbonyl carbon. Recognizing the type of derivative involved in the reaction helps in determining the expected products.
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Product Distribution
In reactions involving nucleophilic acyl substitution, the distribution of products can be classified as major and minor based on factors such as sterics, electronics, and the stability of the resulting compounds. Major products are typically more stable or formed in greater quantities, while minor products may arise from less favorable pathways. Analyzing these factors is essential for predicting the outcome of the reaction.
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