10. Amines - 2010 Department of Chemistry, The University...

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© 2010 Department of Chemistry, The University of Western Ontario 10.1 10. Amines (text 10.1 – 10.5, 10.8) A. Structure and Nomenclature Amines are derivatives of ammonia (NH 3 ), where one or more H atoms have been replaced by an alkyl or aryl group. They have the general formula R 3 N (R = H, alkyl, aryl). If we compare the one-carbon alkane CH 4 to a one-carbon amine CH 3 NH 2 , we notice that each N atom in a molecular formula adds 1 H to the saturated formula. C n H 2n+2+y N y For unsaturation, subtract one H for each N in the molecule o C 3 H 9 N is equivalent to C 3 H 8 = saturated o C 5 H 10 N 2 is equivalent to C 5 H 8 = 2 units of unsaturation This and all the unsaturation calculations described in the previous chapters covers all the common heteroatoms. The rules can be combined and used in complicated formulas. o C 12 H 17 N 2 O 4 Cl equiv. to C 12 H 16 = 5 units unsat. Chemical tests ( e.g. Br 2 and KMnO 4 ) can reveal how many alkene bonds are present, so useful structural information can be obtained from tests and molecular formulas.
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For example, the anti-malarial drug quinine (extracted from a South American tree) has the formula C 20 H 24 N 2 O 2 and therefore has 10 units of unsaturation. Alkyl amines (N single bonded to alkyl C) are classified according to the number of C atoms bonded to the N. Primary RNH 2 Secondary R 2 NH Tertiary R 3 N Quaternary R 4 N + Alkyl amines have N with a full octet, three bonds, sp 3 hybridization, and one lone pair. (except 4°) N atoms with three bonded atoms/groups don’t act as stereocentres. The lone pair rapidly interconverts from one enantiomer to the other and cannot be isolated. However, quaternary ammonium salts can be chiral and have two non- interconverting enantiomers. N
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This note was uploaded on 05/01/2011 for the course CHEMISTRY Chemistry taught by Professor Dr.felixlee during the Fall '11 term at UWO.

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10. Amines - 2010 Department of Chemistry, The University...

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