alcoholrxns - for them *** OTs(Bs) WB WB 4) Substitution...

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Alcohol Reaction Summary Preparation 1) Substitution – a primary alkyl halide plus OH - without heat X OH OH 2) Grignard reactions – a Grignard reagent is RMgX 1 o alcohol: O RMgX, ether 2) H + RC OH formaldehyde RMgX, ether 2) H + RC C OH C C O oxirane 2 o : RMgX, ether 2) H + O OH R an aldehyde 3 o : RMgX, ether 2) H + O HO R a ketone 3) Reduction of aldehydes or ketones – use H 2 /Pt or NaBH 4 /H 2 O O OH H 2 Pt O O NaBH 4 H 2 O 4) Preparation of Phenol NO 2 Sn HCl NH 2 HCl, NaNO 2 cold N 2 H 2 O OH
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Reactions 1) Alkoxide formation -- an alcohol plus an alkali metal (Li, Na, or K) ROH Na or Li or K RO 2) Ether formation: 1 o alkyl halide plus an alkoxide ion: RO X RO Alcohol + acid at 140 o C: OH H 2 SO 4 140 o O (symmetrical ether) 3) Reaction with tosyl chloride (TsCl) or brosyl chloride (BsCl) Ts(Bs)Cl R OH R OTs(Bs) *** - OTs and - OBs are good leaving groups , so you can substitute weak bases
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Unformatted text preview: for them *** OTs(Bs) WB WB 4) Substitution for OH with Br or Cl using PX 3 (X = Br or Cl) R OH R X PX 3 5) Substitution for OH with Cl using SOCl 2 (sulfonyl chloride) R OH R Cl SOCl 2 6) Glycol or Diol formation KMnO 4 or OsO 4 OH HO (syn addition) OH HO RCO 3 H a peroxyacid (anti addition) 7) Mild oxidation of a 1 o alcohol to form an aldehyde (you can only use a mild oxidizer) OH PCC or Cu, 250 C or o Ag 2 O O 8) Oxidation of a 2 o alcohol to form a ketone (you can use a mild or a strong oxidizer) OH PCC or Cu, 250 C or o Ag 2 O O or KMnO 4 or K 2 Cr 2 O 7 (mild oxidizers) (strong oxidizers) 9) Preparation of an ester by an equilibrium reaction of an alcohol with a carboxylic acid OH O OH + O O H 2 O + H +...
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alcoholrxns - for them *** OTs(Bs) WB WB 4) Substitution...

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