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UB CHE 201 Ch 11A
Alcohol Reactions. Given Reactant and Reagent Give Product
| 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 |
Created by:
HugsAndKisses
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