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