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UB CHE 201 Ch 11A

Alcohol Reactions. Given Reactant and Reagent Give Product

1* alcohol + Na2Cr2O7/H2SO4 aldehyde intermediate then to carboxylic acid
2* alcohol + Na2Cr2O7/H2SO4 ketone
1* alcohol + PCC (CrO3+pyridine+HCl) aldehyde
chromic acid test 1* and 2* alcohol will react, 3* wont
Collins reagent original PCC
Jones reagent Dilute Chromic Acid in acetone
NaOCl/H2O good oxidizer for acid sensitive compounds. Takes 1* all the way to a carboxylic acid
alcohol + KMnO4 in base or water 1* to carboxylic acids, 2* to ketones
HNO3/10-20*C 1* to carboxylic acids, 2* to ketones
alcohol + CuO +heat oxidation, not good for lab synthesis due to high temps
alcohol + Cu-Zn/400*C oxidation, not good for lab synthesis due to high temps
alcohol + DMSO + oxyalyl chloride then hindered base (like Et3N) and low temps (Swern Oxidation) to aldehydes and ketones
alcohol + TsCl/pyridine tosylate ester that can react via SN2
alcohol + H2SO4/heat alkene (reduction), can then react to form an alkane catalytically
tosylate ester + LiAlH4 alkane
alcohol + HBr/H2O R-Br
alcohol + NaBr, H2SO4 R-Br
Alcohol + (lucas reagent) HCl/H2O --ZnCl2---> R-Cl
alcohol + PCl3 R-Cl + P(OH)3
alcohol + PBr3 R-Br + P(OH)3
alcohol + PCl5 R-Cl + POCl3 + HCl
R-OH + P + I R-I + P(OH)3
R-OH + thionyl chloride (Cl2-S=O)--heat--> chlorosulfite ester intermediate, then ion pair --> R-Cl + SO2 + HCl
Alcohol ---H2SO4, 180*C --> E1 forms alkene
(2)1* alcohol ---H2SO4, 140*C --> SN2 forms symmetrical dialkyl ethers
diol --H2SO4/100* --> one less OH group, ,ethyl shift to where OH was, double bond to O. PINACOL REARRANGEMENT
alcohol + acid --H+ --> ester + H2O
alcohol + acid chloride ester + HCl
alcohol + sulfuric acid alkyl sulfate ester, add another alcohol --> dialykl sulfate ester. really good leaving group
alcohol + nitric acid alkyl nitrate ester
alcohol + phosphoric acid phosphate ester
Williamson Ether Synthesis 1) form alkoxide with Na, K or NaH 2) Sn2 attack of alkoxide on alkyl halide
less hindered alkyl group (w/ halide or Ts) + more hindered alkoxide williamson ether synthesis
more hindered alky; group (w/ halide or Ts) + less hindered alkoxide elimination
Created by: HugsAndKisses



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