CHAPTER TWENTY Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Aryl esters, that is, compounds of the type RCOAr, are named in an analogous way The names of amides of the type RCNH2 are derived from carboxylic acids by replacing the suffix -oic acid or -ic acid by -amide O CH3CNH, C6H5C ( CH3)2CHCH,CNH Benzamide 3-Methylbutanamide We name compounds of the type RCNHR and RCNr2 as N-alkyl- and N, N-dialkyl substituted derivatives of a parent amide O O CH3CNHCH C,HSCN(CH, CH3) CH3 CH, CH, CNCH(CH3)2 H3 N-Methylacetamide N, N-Diethylbenzamide N-lsopropyl-N-methyl- Substitutive iupac names for nitriles add the suffix -nitrile to the name of the parent hydrocarbon chain that includes the carbon of the cyano group. Nitriles may also be named by replacing the -ic acid or-oic acid ending of the corresponding carboxylic acid with -nitrile. Alternatively, they are sometimes given functional class IUPAC names as alkyl cyanides C6H5C≡N CH3CHCH3 Ethanenitrile Benzonitrile 2-Methylpropaneni (acetonitrile) (isopropyl cyanic PROBLEM 20.1 Write a structural formula for each of the following compounds: (a)2-Phenylbutanoyl bromide (e)2-Phenylbutanamide (b)2-Phenylbutanoic anhydride (f)N-Ethyl-2-phenylbutanamide (c) Butyl 2-F SAMPLE SOLUTION (a)A 2-phenylbutanoyl group is a four-carbon acyl unit that bears a phenyl substituent at C-2. When the name of an acyl group is followed by the name of a halide, it designates an acyl halide CH3CH2 CHCBr 2-Phenylbutanoyl bromide Back Forward Main MenuToc Study Guide ToC Student o MHHE WebsiteAryl esters, that is, compounds of the type , are named in an analogous way. The names of amides of the type are derived from carboxylic acids by replacing the suffix -oic acid or -ic acid by -amide. We name compounds of the type and as N-alkyl- and N,N-dialkyl￾substituted derivatives of a parent amide. Substitutive IUPAC names for nitriles add the suffix -nitrile to the name of the parent hydrocarbon chain that includes the carbon of the cyano group. Nitriles may also be named by replacing the -ic acid or -oic acid ending of the corresponding carboxylic acid with -onitrile. Alternatively, they are sometimes given functional class IUPAC names as alkyl cyanides. PROBLEM 20.1 Write a structural formula for each of the following compounds: (a) 2-Phenylbutanoyl bromide (e) 2-Phenylbutanamide (b) 2-Phenylbutanoic anhydride (f) N-Ethyl-2-phenylbutanamide (c) Butyl 2-phenylbutanoate (g) 2-Phenylbutanenitrile (d) 2-Phenylbutyl butanoate SAMPLE SOLUTION (a) A 2-phenylbutanoyl group is a four-carbon acyl unit that bears a phenyl substituent at C-2. When the name of an acyl group is followed by the name of a halide, it designates an acyl halide. CH3CH2CHCBr C6H5 O 2-Phenylbutanoyl bromide Ethanenitrile (acetonitrile) CH3C N Benzonitrile C6H5C N 2-Methylpropanenitrile (isopropyl cyanide) CH3CHCH3 C N N-Methylacetamide CH3CNHCH3 O N,N-Diethylbenzamide C6H5CN(CH2CH3)2 O N-Isopropyl-N-methyl￾butanamide CH3CH2CH2CNCH(CH3)2 O CH3 RCNR 2 O X RCNHR O X CH3CNH2 O X Acetamide C6H5CNH2 O X Benzamide (CH3)2CHCH2CNH2 O X 3-Methylbutanamide RCNH2 O X RCOAr O X 776 CHAPTER TWENTY Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website