chem 348 reagents – Flashcards
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| CH2I2, Zn (Cu) Et2O2 |
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| Simmons Smith (alkene->Carbene) |
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| O3 CH2Cl2 -78 |
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| Ozonolysis (alkene-> aldehyde) |
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| KMnO4 |
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| Oxidative Cleavage (Alkene-> carboxylic acids) |
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| ? |
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| Cyclopropanation |
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| OsO4 NaIO4 THF or tBuOH when using KMnO4: |
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| Periodate cleavage (alkene to ald/ketone) KMno4= carboxyic acids |
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| HgSO4 H2SO4 |
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| Hydration of Alkynes (alkyne to carboxylic acid or ketone) |
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| NBS hv CCl4 |
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| Allylic or Benzylic Bromination (addition of bromine to allylic or benzylic carbon) |
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| 1.) 9 BBN 2.) H2o2, NaOH |
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| Hydration of Alkynes (alkyne to Aldehyde) |
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| 1.) Hg(OAc)2, H20 2.) NaBH4 |
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| oxymercuration reduction (alkene to OH on markovnikov carbon) |
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| 1.) BH3 THF 2.) NAOH H2O2 |
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| Hydroboration oxidation (alkene to OH on antimarkovnikov carbon) |
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| -:CH2 |
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| Carbene formation (alkene to carbene) |
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| H2N NH2 KOH |
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| Wolff Kishner RXN Ketone taken off |
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| 1. CH3-NH2, H+, -H2O 2. NaBH4/MeOH |
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| Reductive amination (Ketone->Imine-> Amine) |
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| Starting w/ Benzene: 1.) HNO3 2.) SNCl2/HCL MeOH 3.) NaNO2/H2SO4 |
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| formation of diazonium ion N triple bond N good LG |
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| Diazonium + CuCl |
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| chlorbenzene |
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| Diazonium + CuBr |
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| bromobenzene |
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| Diazonium + NaI |
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| Iodine-benzene |
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| Diazonium + H3PO2 |
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| Benzene |
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| Diazonium + phenol and NaOH |
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| azo dye |
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| Diazonium + Ch3OH |
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| Reflux benzene-OCH3 |
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| Diazonium + H20, 100 C OR Cu2O, Cu(NO3)2 |
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| phenol |
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| Diazonium + CuCn |
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| benzene w/ nitrile |
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| t-butyl benzene + H2CrO4, H2SO4/H2O, heat |
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| side chain oxidation (benzene disapears, carboxylic acid w/t-butyl on it) |
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| Na2CrO7, H2O2, Aceton |
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| Jones Oxidation secondary alcohol to Ketone |
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| 1.DMSO, (COCl)2 CH2Cl2 -60 2.Et3N -20 |
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| Swern Oxidation primary alcohol to aldehyde |
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| periodinane -HOAc |
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| Primary alchol to aldehyde |
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| LDA, THF, -78C |
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| product of kinetic enolate |
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| Ph3P=CHCH2Ch3 +aldehyde or ketone |
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| wittig (carbonyl to alkene) |
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| 1.) NaH, THF b.) PhCHO |
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| Emmons-horner reaction (carbonyl to alkene) |
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| NaCN, H+ aldeh/ketone |
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| formation of cyanohydrin |
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| TMSCN |
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| cyanohydrin protecting group |
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| ketone + HONH3CL, py or NaOAC |
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| oxime formation |
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| oxime+ PCl5 or H2SO4 |
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| Beckmann Rearrangement |
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| CN DIBAL (1eq) |
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| Reduction to CHO |
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| CN DIBAL (2eq) |
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| Reduction to NH2 |
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| CO2H DIBAL (2eq) |
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| Reduction to CHO |
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| Ester DIBAL (1eq) |
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| Reduction to CHO |
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| Br2, HOAc + carbonyl |
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| alpha halogenation |
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| ketone + mcpba |
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| ester |
