Ch18 Amines(pdf) - KFUPM Open Courseware

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Example: Ammonia gives a primary amine.Example: Primary amines give secondary aminesOH 2 , NiHCH 3 (CH 2 ) 5 CH+ H 2 NO + NH 3ethanolNH 2H 2 , Ni ethanol(80%)CH 3 (CH 2 ) 5 CH 2 NH(65%)via:NHExample: Primary amines give secondary aminesExample: Secondary amines give tertiary aminesOCH 3 (CH 2 ) 5 CH+ H 2 NOCH 3 CH 2 CH 2 CH+NH 2 , Ni ethanolH 2 , Ni, ethanolHCH 3 (CH 2 ) 5 CH 2 NH(65%)via:CH 3 (CH 2 ) 5 CHNNCH 2 CH 2 CH 2 CH 3(93%)
Example: Secondary amines give tertiary aminespossible intermediates include:NN+18.4 CThe Hofmann RearrangementHOCHCH 2 CH 2 CH 3CHCH 2 CH 2 CH 3NCHCHCH 2 CH 3The Hofmann RearrangementExamplesTreatment of amides with bromine in basic solutiongives an amine with loss of the carbonyl carbon.ORCNH 2Br 2HO –RNH 2+ CO 2– 3O(CH 3 ) 3 CCH 2 CNH 2OCNH 2Br 2 , NaOHH 2 OBr 2 , KOHH 2 O(CH 3 ) 3 CCH 2 NH 2(94%)NH 2BrBr(87%)
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: Synthesis of Amines via AmidesOCOHo
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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