Textbook Question
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(c)
22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
3:21 minutesProblem 9a,b
Textbook Question
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH3)
Verified step by step guidance1
Identify the general reaction for amide synthesis: Amides can be synthesized by reacting an acyl chloride with an amine. The reaction involves nucleophilic acyl substitution, where the amine attacks the carbonyl carbon of the acyl chloride, leading to the formation of the amide and the release of HCl.
For part (a), N,N-dimethylacetamide: Determine the required acyl chloride and amine. The structure of N,N-dimethylacetamide suggests that the acyl chloride should be acetyl chloride (CH3COCl), and the amine should be dimethylamine ((CH3)2NH).
Write the reaction for part (a): Combine acetyl chloride (CH3COCl) with dimethylamine ((CH3)2NH). The reaction proceeds as follows:
For part (b), acetanilide (PhNHCOCH3): Determine the required acyl chloride and amine. The structure of acetanilide suggests that the acyl chloride should again be acetyl chloride (CH3COCl), and the amine should be aniline (PhNH2).
Write the reaction for part (b): Combine acetyl chloride (CH3COCl) with aniline (PhNH2). The reaction proceeds as follows:
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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom. They are highly reactive towards nucleophiles, making them useful in organic synthesis, particularly for forming amides. In the context of the question, acyl chlorides can be reacted with amines to produce the desired amides.
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Recognizing acyl chlorides and anhydrides.
Amines
Amines are organic compounds that contain nitrogen atoms bonded to carbon atoms. They can act as nucleophiles due to the lone pair of electrons on the nitrogen, allowing them to react with electrophiles like acyl chlorides. In synthesizing amides, the amine reacts with the acyl chloride to form the amide bond, releasing hydrochloric acid as a byproduct.
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Amide Formation
Amide formation is a key reaction in organic chemistry where an amine reacts with a carboxylic acid derivative, such as an acyl chloride, to produce an amide. This reaction typically involves nucleophilic attack by the amine on the carbonyl carbon of the acyl chloride, leading to the formation of the amide bond (C=O-N). Understanding this mechanism is crucial for synthesizing specific amides like N,N-dimethylacetamide and acetanilide.
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