Reaction from 236 - Chem 436 Spring 2009 Reactions to...

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Cl OH OH OH RX HCl Mg ether HO SOCl 2 pyridine ArSO 2 Cl ZnCl 2 h ν Br 2 RMgX OH OSO 2 Ar Cl Cl Br Br Br Chem 436, Spring 2009 Free radical halogenation Reactions to review from Chem 236 • chlorination not selective • bromination selective for 3° > 2° > 1° hydrogen • initiation, propagation, termination steps Formation of Grignard reagents • cannot have hydroxyl group in same molecule • usually lose stereochemistry at attached carbon Nucleophilic substitution reactions (S N 2 and S N 1) Basic hydrolysis of alkyl halides • S N 2 rxn, therefore only for non- β -branched 1° RX Conversion of alcohols into alkyl halides • form ROH 2 + intermediate • S N 2 rxn if 1° alcohol • S N 1 rxn if 2° or 3° alcohol Reaction of an alcohol with SOCl 2 or PBr 3 • S N 2 reaction • inversion of configuration • 3° alcohols do not form halide Use of sulfonate esters to assist displacement reactions • arenesulfonate (ArSO 3 ) good leaving group • useful when don't want racemic product – 1 –
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O OH Cl O OH Cl Br Br CH 3 O CH 3 OH H + O 2 H + , Δ – H 2 O NaH RO tBuO tBuO OCH 3 OH O OOH OH OCH 3 O OR Carbocation rearrangements
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Reaction from 236 - Chem 436 Spring 2009 Reactions to...

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