Chapter 19 - Chapter 19 Carboxylic Acid Derivatives:...

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Chem 212 B. R. Kaafarani 1 Chapter 19 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
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Chem 212 B. R. Kaafarani 2 RC O X Acyl Halides Name the acyl group and add the word chloride , fluoride , bromide ,or iodide as appropriate Acyl chlorides are, by far, the most frequently encountered of the acyl halides 19.1. Nomenclature of Carboxylic Acid Derivatives
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Chem 212 B. R. Kaafarani 3 CH 3 C Cl O Acetyl chloride 3-Butenoyl chloride O H 2 C CHCH 2 C Cl O C Br F p -Fluorobenzoyl bromide Acyl Halides
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Chem 212 B. R. Kaafarani 4 RC O CR' O O Acid Anhydrides When both acyl groups are the same, name the acid and add the word anhydride. When the groups are different, list the names of the corresponding acids in alphabetical order and add the word anhydride.
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Chem 212 B. R. Kaafarani 5 Acetic anhydride Benzoic anhydride Benzoic heptanoic anhydride CH 3 C O CCH 3 O O C 6 H 5 C O CC 6 H 5 O O C 6 H 5 C O C(CH 2 ) 5 CH 3 O O Acid Anhydrides
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Chem 212 B. R. Kaafarani 6 RC O R' O Esters Name as alkyl alkanoates. Cite the alkyl group attached to oxygen first ( R' ). Name the acyl group second; substitute the suffix -ate for the -ic ending of the corresponding acid.
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Chem 212 B. R. Kaafarani 7 CH 3 C O CH 2 CH 3 O Ethyl acetate Methyl propanoate 2-Chloroethyl benzoate O CH 3 CH 2 C O CH 3 C O CH 2 CH 2 Cl O Esters
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Chem 212 B. R. Kaafarani 8 RC NH 2 O Amides having an NH 2 group Identify the corresponding carboxylic acid. Replace the -ic acid or -oic acid ending by –amide.
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Chem 212 B. R. Kaafarani 9 CH 3 C NH 2 O Acet amide 3-Methylbutan amide O (CH 3 ) 2 CHCH 2 C NH 2 C NH 2 O Benz amide Amides having an NH 2 group
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Chem 212 B. R. Kaafarani 10 RC NH R' O and RC N R' 2 O Amides having substituents on N Name the amide as before. Precede the name of the amide with the name of the appropriate group or groups. Precede the names of the groups by the letter N- (standing for nitrogen and used as a locant).
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Chem 212 B. R. Kaafarani 11 CH 3 C NH CH 3 O N - Methyl acetamide N - Isopropyl - N - methyl butanamide C N (CH 2 CH 3 ) 2 O N , N - Diethyl benzamide O CH 3 CH 2 CH 2 C N CH(CH 3 ) 2 CH 3 Amides having substituents on N
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Chem 212 B. R. Kaafarani 12 RC N Nitriles Add the suffix -nitrile to the name of the parent hydrocarbon chain (including the triply bonded carbon of CN). Or: replace the -ic acid or -oic acid name of the corresponding carboxylic acid by –onitrile. Or: name as an alkyl cyanide (functional class name).
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Chem 212 B. R. Kaafarani 13 CH 3 C N Ethanenitrile or: Acetonitrile or: Methyl cyanide C 6 H 5 C N Benzonitrile N C CH 3 CHCH 3 2-Methylpropanenitrile or: Isopropyl cyanide Nitriles
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Chem 212 B. R. Kaafarani 14 Figure 19.1 (page 816) The key to managing the information in this chapter is the same as always: structure determines properties.
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This note was uploaded on 01/06/2012 for the course CHEM 212 taught by Professor Bilalkaafarani during the Fall '10 term at American University of Beirut.

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Chapter 19 - Chapter 19 Carboxylic Acid Derivatives:...

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