Question | Answer |
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 |