organic chem slides

organic chem slides - CHAPTER 11 AMINES DERIVATIVES OF...

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204 AMINES DERIVATIVES OF AMMONIA ELECTRONIC STRUCTURE N N N N H H H H H H R R R R' R' R" Primary Amine Secondary Amine Tertiary Amine Ammonia R R R R = H or Alkyl group unshared electron pair N CHAPTER 11
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205 Specify the alkyl groups attached to the nitrogen and add the suffix – amine. CH 3 CH 2 NH 2 (CH 3 ) 2 NH (CH 3 CH 2 ) 3 NH ethylamine dimethylamine triethylamine Ethyl,methylamine NAMING I- COMMON NAMES II- IUPAC NAMES The –NRR’ group is treated as a substituent and is called the amino group . CH 3 CHCH 2 CH 3 NH 2 CH 3 CHCH 3 NHCH 3 H 2 N NHC 2 H 5 H H 2-aminobutane 2-methylaminopropane Trans-1-amino-3-ethylaminocyclopentane
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206 PREPARATION N H H H + RX N H H H R + X + nucleophillic substitution Treatment of the ammonium salt with OH - yields the amine. N H H H R + + OH N H H R + H 2 O
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207 N H H R + + H 2 O R' X N H H R + R' OH N H R R' N H R + + H 2 O X N H R + R' OH N R R' R' R" R" R" N R + X N R + R' R' R" R" R"' R"' secondary tertiary quaternary ammonium salt
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208 BASCICITY T h e u n s h a r e d p a i r o f e l e c t r o n s o n t h e n i t r o g e n a t o m o f a m m o n i a a n d a m i n e s n o t o n l y m a k e s t h e m n u c l e o p h i l e s b u t a l s o B r o n s t e d b a s e s . Amines react with water as shown below N + H OH N H + + OH K B
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209 GAS PHASE Electron donating inductive effect stabilizes the ammonium ion by delocalizing the + charge. Thus amine becomes more basic. N R N R N R N R' R' R" H H H H H H N + H OH N H + OH K B R R δ + δ + tertiary secondary primary ammonia
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210 AQUEOUS PHASE I- Hydrogen bonding of ammonium ion stabilizes the ammonium ion which makes the amine more basic. II- The greater the number of hydrogen bonds the more basic the amine. N R N R N R N R' R' R" H H H H H H ammonia primary secondary tertiary
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211 Type of amine Amine Ammonium ion K B Ammonia NH 3 NH 4 + 10 -4.7 Primary CH 3 NH 2 CH 3 NH 3 + 10 -3.6 Secondary (CH 3 ) 2 NH (CH 3 ) 2 NH
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organic chem slides - CHAPTER 11 AMINES DERIVATIVES OF...

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