Ch18 Amines(pdf) - KFUPM Open Courseware

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Cleavage of Alkylated PhthalimideO•• N R + H O 2Oacid or baseCO 2 HCO 2 H+H 2 Nimide hydrolysis isnucleophilic acylsubstitutionRCleavage of Alkylated Phthalimidehydrazinolysis is an alternative method of releasingthe amine from its phthalimide derivativeO••N ROH 2 NNH 2+OOH 2 NNHNHRExampleExampleOO–•• N • K ++ C 6 H 5 CH 2 Cl–•• N • K ++ C 6 H 5 CH 2 ClODMFODMFO•• NCH 2 C 6 H 5(74%)O
ExampleOONHNH+ C 6 H 5 CH 2 NH 2H 2 NNH 2(97%)The Gabriel’s s synthesis to prepareα-amino acidsO•• NCH 2 C 6 H 5OFirst: Reaction with alkyl malonateO–•• N • OK ++ BrCH(CO 2 C 2 H 5 ) 2Diethyl bromomalonateSecond: Treatment with baseO•• NOCH(CO2 C 2 H 5 ) 2+ C 2 H 5 O -EthoxideOO•• NCH(CO 2 C 2 H 5 ) 2•• N• •C(CO2 C 2 H 5 ) 2OO
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: Gabriel Synthesisgives primary amin
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 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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