Ch18 Amines(pdf) - KFUPM Open Courseware

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CH 2 CH 3+NCH 2 CH 3CN –+MechanismCH 3 CH 2 CH 2 CH 2 BrCH 2 CH 3(in butyl bromide)18.8Nitrosation of AlkylaminesCH 2 CH 3+NCH 2 CH 3CH 2 CH 3(in butyl bromide)Br –+CH 3 CH 2 CH 2 CH 2 CNNitrite Ion, Nitrous Acid, and Nitrosyl CationNitrosyl Cation and Nitrosation–••••O••••NO •• • H +HO ••••••NH +O •• • H•• O • H+••N+O •• • H+•• OHN•• O •• • ••N+O •• •
Nitrosyl Cation and NitrosationNitrosation of Secondary Alkylamines+N••NO •• • +N••NO •• • •• N••NO •• • H++HN • •+••N+O •• • HN • •+••N+O •• • nitrosation ofsecondary aminesgives an N-nitrosoamineExampleSome N-NitrosoNNitroso <strong>Amines</strong>(CH 3 ) 2 N N O N-nitrosodimethylamine(leather tanning)(CH 3 ) 2 NH••NaNO 2 , HClH 2 O••(CH 3 ) 2 NN•• (88-90%)O •• • NNONNNON-nitrosopyrrolidine(nitrite-cured bacon)N-nitrosonornicotine(tobacco smoke)
Page 1 and 2: Chapter 18Amines18.1Amine Nomenclat
Page 3 and 4: Secondary and Tertiary AminesName a
Page 5 and 6: Geometry at NCompare geometry at N
Page 7 and 8: Physical Propertiesboilingpoint:CH
Page 9 and 10: Preparation of AminesTechniques fal
Page 11 and 12: Gabriel Synthesisgives primary amin
Page 13 and 14: ExampleOONHNH+ C 6 H 5 CH 2 NH 2H 2
Page 15 and 16: Synthesis of Amines via AzidesS N 2
Page 17 and 18: Synthesis of Amines via AmidesOCOHo
Page 19 and 20: Example: Secondary amines give tert
Page 21 and 22: Step 2••O••••-•• O
Page 23 and 24: Basicity Constant (K b ) and pK bK
Page 25 and 26: Basicity of Amines in Aqueous Solut
Page 27 and 28: Effect of Substituents on Basicity
Page 29 and 30: ImidazoleWhich nitrogen is protonat
Page 31: (aqueous)CH 2 CH 3+NCH 2 CH 3CH 2 C
Page 35 and 36: Nitrosation of Primary AlkylaminesN
Page 37 and 38: Nitrosation of N-AlkylarylaminesNsi
Page 39 and 40: The Hofmann EliminationMechanismon

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