Ch18 Amines(pdf) - KFUPM Open Courseware

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Mechanism of the Hofmann RearrangementStep 1ORCNH 2ORCNHBrRNCORNH 2The Hofmann rearrangement involves 6 stepsin 3 stages.1. formation of an N-bromoamide (2 steps)2. conversion of the N-bromoamide to anisocyanate (2 steps)3. hydrolysis of the isocyanate (2 steps)RCH••O•••• NH– •• •• O••HStep 1Step 2••O••••–•• O••••–•• O••RCH•• NH– •• •• O••HRCH•• N•• O••HHRCH•• N•••• Br••••Br••••
Step 2••O••••–•• O••Step 3••O••RCRCRCH•• N••Br•••••• Br•• • –••H•• N•••• Br••••Br••••H•• N••Br••••– •• •• O••HStep 3Step 4••O••••–•• O••••O••••–•• O••RCRCCRCH•• N••Br•••••• N••Br••••HRN •••• Br•• • –••N••••Br••••– •• •• O••H•• O••H
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: Example: Secondary amines give tert
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 and 32: (aqueous)CH 2 CH 3+NCH 2 CH 3CH 2 C
Page 33 and 34: Nitrosyl Cation and NitrosationNitr
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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