Chap19 chem12B

Chap19 chem12B - Chap 19 Amines O N OCH3 N CH3 O Ph N O...

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1 Chap 19 Amines N O OCH 3 O O Ph cocain N N CH 3 nicotine N N H H N H N N N N H indole N H piperdine pyridine aziridine pyrole pyrolidine imidizole 1. Chirality - Amines introconvert with lone pair and lose stereochemistry. N CH 2 Ch 3 (R) N CH 2 Ch 3 (S)
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2 Two ways to get a chiral amine. 1) Quaternary salt. N Ph + 2) ring strained system (small ring) N lone pair cannot introconvert. 2. Physical properties Basicity- R NH 2 + HX R NH 3 + + X- R groups are e’ donating, additional R groups make it more basic but 1,2 and 3 all have about the same bascity due to decreasing solubility of adding more R groups. hybridization N H 3 C C N pKb 2.88 8.75 24 sp 3 sp 2 sp 3. Electrophilic Aromatic Substitution.
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3 A) Pyrole N H + H 3 C O CH 3 O O Friedel-Crafts N H CH 3 O + HOAc N H N H E E+ N H E + N H E + N H E + B) Pyridine, non-bonding π e’ perpendicular to ring. Electrophilic N is e’ withdrawing by induction, deactivating and meta director. 1) electrophilic N + NO 2 + N NO 2 also get N + E N E + resistant to further substitution. Why. N + NO 2 + N NO 2 + bad other resonance
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4 N + NO 2 + N NO 2 + N NO 2 + N NO 2 + better 2) substitution rxn, Lv group has to be ortho para, activating towrd nucleophiles. N
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Chap19 chem12B - Chap 19 Amines O N OCH3 N CH3 O Ph N O...

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