Chapter 10 -Reaction of Alcohols

I.  Oxidation-Reduction 
	Oxidation :  loss of H2; addition of O or O2; addition of X2
	Reduction:  addition of H2 or H_; loss of O or O2; addition of X2
II.  Oxidation of Alcohols
	A.  Secondary alcohol--------> ketone
		chromic acid reagent (potassium dichromate and sulfuric mixture)
		mechanism involves the initial formation of a chromate ester followed by 
		elimination of hydrogen attached to OH carbon and CrO3H
	B.  Primary alcohol
		1.  all-the way - chromic acid reagent or KMnO4
		RCH2OH ------->  RCHO -------->  RCO2H
		2.  Stopping at the aldehyde stage - PCC
	C.  Tertiary alcohols - no reaction at normal temperatures used in oxidation
	D.  Biological Oxidation
		ethanol goes to ethanal in the presence of NADH+ and ADH (alcohol 
dehydrogenase); NADH+  is converted to NAD.  Transfer of a pro-R hydrogen to the front 
face of the pyridine ring in NADH+ .  The process is repeated for the conversion of 
acetaldehyde to acetic acid.
III. Alcohols as Nukes
	A.  Formation of Tosylate esters - read section 10-7.
	B.  Alkoxide formation and subsequent E-2 reactions
IV.  Alcohols as Electrophiles
	A.  Reaction of Alcohols with HX
		ROH   +    HX -------RX +  HOH
		HBr is the most general acid used - Reacts with primary, sec and tert 
alcohols
		HCl  reacts ok with secondary and tertiary alcohols, but not primary
			use Lucus reagent to get primary alcohols to react (ZnCl2/ HCl
		HI gives low yields
	READ about limitations on p. 446.
	B.  Reaction of Alcohols with PX3
		Work best with primary and secondary alcohols
		SN2 displacement of dihalophosphorus from intermediate - stereochemistry
		inversion of configuration
	C.  Reaction of Alcohols with SOCl2 - retention of configuration under some
	conditions.
	D.  Dehydration of alcohols - read p. 450 to 454.
	E.  Unique Reaction of pinnacol ---pinacalone.