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FUNCTIONAL GROUPS Other Organic Functional Groups Alcohols • Organic compounds with one or more hydroxyl groups, -OH • General formula: CnH2n+1OH • Three classes of alcohols: R C R'' H H OH H Primary, 1 R C OH R' Secondary, 2 R C OH R' Tertiary, 3 Naming of Alcohols • The longest carbon chain containing the –OH group is chosen • The position of the –OH group is indicated by the smallest possible number • Ending changes to -ol Examples 1- Propanol 2- Propanol 2-methyl-2-propanol 5 5 2 OH 3 4 OH Pentane Pentane-2,4-diol ‘e’ is retained in diol 6 1 Phenols 7 • Derived from aromatic hydrocarbons • Contain one or more –OH groups attached to an aryl group Ar – OH Aryl group Hydroxyl group OH OH 1 OH 8 2 Phenol Benzene-1,2-diol 2-hydroxyphenol OH 1 Cl OH OH 1 1 2 3 4 Cl 2-chlorophenol 3-chlorophenol 4-chlorophenol o-chlorophenol m-chlorophenol p-chlorophenol o ortho m meta p para 9 Cl Aldehydes • Organic compounds that contain a H-C=O group • The C=O is called a carbonyl group • Product of the dehydrogenation of alcohols H R C R O C H O + H H • The aldehyde group, -CHO, always occupies the terminal position • Therefore, no need to specify its position • Ending changes to -al H2 Examples O O O O H H H H Methanal Ethanal AKA Formaldehyde H Propanal Benzaldehyde Ketones • Organic compound that contains a carbonyl group with no H atom directly attached to it R C O 'R • Only need to specify position in carbon chain when ketone can be in multiple positions • Ending changes to -one Examples Propanone – AKA acetone Butanone – AKA Methyl Ethyl Ketone 2-Pentanone - Note the number is necessary because the C=O could be on carbon 2 or carbon 3 Examples O 4 2 O 2 3 4-methyl-2-pentanone 2-methyl-3-pentanone Examples 3 O O O 2 4 2 O Pentane-2,3-dione Pentane-2,4-dione Carboxylic Acids • Organic compounds that contain a carboxyl group O C Carbonyl = Carboxyl OH Hydroxyl • The carboxyl group, -COOH, always occupies the terminal position • No need to specify its position • Ending changes to –oic acid Examples O O O OH OH OH H Methanoic acid Ethanoic acid Propanoic acid Butanoic acid Examples COOH COOH COOH 1 OH 1 2 3 Benzoic acid 2-hydroxybenzoic acid 3-methylbenzoic acid Esters • Derived from a carboxylic acid and an alcohol O R C + O HO R' H2O H O R C O Ester • When naming esters: • Carbon chain containing C=O gets suffix • Ending changes from –oic acid to –oate • Name of “R” group from alcohol precedes R' Examples O O Methyl Ethanoate spacing Ethyl butanoate Butyl ethanoate Ethers • Organic compounds that contain an oxy, -O-, group R O oxy group R • When naming, the oxy groups are always treated as substituents and expressed as prefixes Examples methane O ethoxy ethoxymethane 22 Examples O ethane methoxy methoxyethane Examples O phenoxy methane phenoxymethane Examples benzene O methoxy methoxybenzene Examples 1 2 3 propane O methoxy 2-methoxypropane Amines • Organic compounds that are derivatives of ammonia, NH3 H N H R Primary(1°) amine H NH3 N R Secondary(2°) amine 'R ''R N 'R R Tertiary (3°) amine Naming Primary Amines • When the amino group is attached to a hydrocarbon family like CC, C=C, X- and RO-, the amine group is always treated as the principal functional group and expressed as a suffix • Ending changes to –amine methanamine NH2 NH2 NH2 ethenamine (ethylenamine) ethynamine (acetylenamine) Naming Primary Amines • When naming amine groups with other functional groups, the amino group is always treated as the substituent and expressed as a prefix, amino- 2 HO 1 NH2 2-aminoethanol Naming Secondary and Tertiary Amines • Use the designation “N” to state group that is directly attached to amine group N-methylmethanamine NH N-methylethanamine NH Examples N N N,N-dimethylethanamine N,N-dimethylmethanamine Aromatic Amines NH2 NOT benzenamine phenylamine or aniline Examples NH2 NH 2-methylaniline N-methylaniline N-phenylmethanamine Formation of Primary Amides • Organic compound that is derived from a carboxylic acid and an amine O R C + H NH2 OH H2O O R C NH2 1° amide N links to only ONE C • The amide group always occupies the terminal position in a primary amide • No need to specify its position • Suffix of –amide is used Examples of Primary Amides O Ethanamide NH2 Butanamide Formation of Secondary Amides O R + C OH H H2O NH R' 1o amine O R C HN R' 2° amide N links to TWO C atoms • When naming secondary and tertiary amides: • Carbon chain containing C=O gets suffix, –amide • Use the designation “N” to state R group that is directly attached to amine group Formation of Tertiary Amides O R'' O R + C H N H2O R C N R' R' OH 2o amine ''R 3° amide N links to THREE C atoms Examples O N-methyl ethanamide HN NO spacing O N,N-dimethylethanamide N Nitriles • Compounds that contain the cyano group, -CN • If acting as the principal functional group: • The carbon of the -CN group is counted as part of the longest carbon chain • The -CN group always occupies the terminal position so no need to specify its position • Ending changes to –nitrile C 1 3 2 ethanenitrile N C N 2-methylpropanenitrile Nitriles • If acting as the substituent: • The carbon of the -CN group is NOT counted as part of the longest carbon chain • The prefix, cyano-, is used N 1 HOOC 2 3 C 3-cyano-2-methylpropanoic acid A Summary of All Organic Compounds Alkane Alcohol Carboxylic acid O OH OH Alkene Ether Amine NH2 O Alkyne C Ketone Amide O O C NH2 Haloalkane Aldehyde Amino acid O O Cl Br H2N H OH