Ch18 Amines(pdf) - KFUPM Open Courseware

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1 H NMR13 C NMRcompare chemical shifts in:Carbons bonded to N are more shielded thanthose bonded to O.H 3 CCH 2 NH 2 H 3 C CH 2 OHδ 3.9 ppm δ 4.7 ppmCH 3 NH 2CH 3 OHN C H is more shielded thanO C Hδ 26.9 ppm δ 48.0 ppmMass SpectrometryCompounds that contain only C, H, and Ohave even molecular weights. If an odd numberof N atoms is present, the molecular weight isodd.A molecular-ion peak with an odd m/z valuesuggests that the sample being analyzedcontains N.18.4Preparation of Amines
Preparation of AminesTechniques fall into three major categories:1) Nucleophilic Substitution2) Reduction3) Amide rearrangement18.4 APreparation of Aminesby Alkylation of AmmoniaDesired reaction is:Alkylation of Ammonia2 NH 3 + R—X R—NH2+ NH 4 XDesired reaction is:Alkylation of Ammonia2 NH 3 + R—X R—NH2+ NH 4 Xvia:H 3 N • + R•• + •• X •• H 3 N R ••–+ •• X •• ••then:H 3 N • + HH++N R H 3 N H +H•• NRHH
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: Physical Propertiesboilingpoint:CH
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 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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