Amines Amines (e.g. RNH 2 ) are organic derivatives of ammonia, NH 3 similar to ammonia
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1 148Exam 2 notes rganic hemistry (e.g. 2 ) are organic derivatives of ammonia, 3 similar to ammonia omenclature: suffix 2 prefix 2 ( 3 ) 2 Types: Primary (1 o ), secondary (2 o ), tertiary (3 o ) or quaternary ammonium cations (4 o ). Structure : 3 2 l _ ame ammonia ethyl amine Type dimethyl amine trimethyl amine tetramethyl ammonium 148
2 149Exam 2 notes Physical Properties: ydrogen bonding? Melting points: Boiling points: rganic hemistry Solubility in aqueous media: Structure: eactivity: The important organic reactions of amines 1. As bases with common acids: 2. As nucleophiles with the common electrophiles: A) B) ) 149
3 150Exam 2 notes Acidity: rganic hemistry 3 a a 2 1. a 2 2. 'X ' X X a 2 2 -X X Basicity: X a 2 2 -X
4 151Exam 2 notes Aryl amines: rganic hemistry 2 The basicity of aryl amines is: Increased by: Decreased by: 2 eteroaromatic compounds: 151
5 152Exam 2 notes rganic hemistry Preparation of Ammonia Alkylation Phthalimide Alkylation -X X - 1. K 2. -X eductions: Azides [] 2 itriles [] 2 2 itro Ar 2 [] Ar 2 Amides 2 LiAl eductive Amination ' " 2 2. [] " 2 ' 152
6 153Exam 2 notes rganic hemistry Alkylation of Ammonia by Alkyl alides -X X - 3 -X 2 -X 2 -X 3 -X 4 X MEAISM F AMMIA ALKYLATI ' 2 2 _ Br 2 ' ' 2 ' 2 2 ' 153
7 154Exam 2 notes rganic hemistry Alkylation of Phthalimide eaction type: Advantage: Disadvantage: Mechanism: 1. K 2. -X _ 2 Br
8 155Exam 2 notes eduction of Azides eaction type : verall reaction: eagents : rganic hemistry [] 2 eduction of itriles xidation number eaction type: verall eaction: eagents : [] 2 2 eduction of itro ompounds [] Ar 2 Ar 2 eaction type : itroarenes can be reduced to primary aryl amines eagents: Importance: eduction of Amides 2 LiAl 4 eaction type: verall reaction: ' 2, reduced to, 2 ' 2 Typical reagents : Products:
9 156Exam 2 notes rganic hemistry LiAl 4 Mechanism: LiAl 4 LiAl 4 ' ' " ' ' " '" Li Al 3 Al 2 '" '" Li Al 3 '" 156
10 157Exam 2 notes rganic hemistry eductive Amination via Imines or Eneamines eaction type : verall eaction: Typical reagents : step 1 : step 2 : Importance: ' " 2 Then educe " 2 ' eactions of 1. ucleophilic substitution alkyl halides 2. ucleophilic addition aldehydes or ketones 3. ucleophilic acyl substitution carboxylic acid derivatives, 157
11 158Exam 2 notes rganic hemistry Alkyl alides -X X - Aldehydes and Ketones arboxylic acid deriviatives 2 ' " 2 ' " 2 l ' 2 Then educe " 2 ' ' Base '2 ' 2 Base '2 " 2 2 ofmann Elimination 2 1. Excess 3 I 2. Ag 2 / 2 ( 3 ) 3 2 Electrophilic Aromatic Substitution E E Diazotization E itrosation 2 ' 2 '
12 159Exam 2 notes rganic hemistry Alkylation of by Alkyl alides -X 2 ' 3 ' 3 X - ' 3 -X 2 -X 2 -X 3 -X 4 X eaction of with Aldehydes and Ketones Primary amines Secondary amines ' " 2 2 ' " 2 Then educe ' " " 2 ' eaction type: ucleophilic Addition then Elimination 1 amines: 2 amines: Preparation of Amides l ' 2 Base '2 2 2 eaction type: ' 2 Base '2 eagents: Limitations: 159
13 160Exam 2 notes ofmann Elimination rganic hemistry 1. Excess 3 I 2 2. Ag 2 / 2 eaction type: eagent: Mechanism: ( 3 ) I = Ag 2 2 :( 3 ) 3 2 egioselectivity: ofmann product 2 1. Excess 3 I 2. Ag 2 / 2 EAT ( 3 ) 3 Selectivity: B3 3 B 3 B
14 161Exam 2 notes rganic hemistry Electrophilic Aromatic Substitution E E E Limitation: Problem: 2 2 Br 2 2 l or 161
15 162Exam 2 notes rganic hemistry Diazotization of primary amines itrosation of secondary amines 2 ' 2 ' 2 2 eagents: Mechanism for diazotization reaction of Primary alkyl or aryl amines 2 162
16 163Exam 2 notes rganic hemistry Mechanism for Secondary alkyl or aryl amines 2 Tertiary alkyl amines Tertiary aryl amines Useful eactions Aryl Diazonium Ions Schiemann reaction Sandmeyer reactions Azo Dyes l ul ubr Br 3 P 2 or Ethanol 2, 2 S 4 eat (100 o ) 2 KI BF 4 u I F 163
17 164Exam 2 notes rganic hemistry Spectroscopic Analysis I Absorbance (cm -1 ) M - Interpretation esonance (ppm) (broad, exchangeable) M Interpretation esonance (ppm) Interpretation UV-VIS Mass Spectrometry ( 3 ) The nitrogen rule: 1. o nitrogens 2. odd number of atoms 3. even number of atoms ( 3 )
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