Alcohol Synthesis(New Reactions). Given Reactant and Reagent Give Product
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| R-X + Mg ---ether--> | R-Mg-X, grignard reagent
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| R-X + 2Li ---> | R-Li(organolithium reagent) + Li+-X
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| Formaldehyde + R-MgX --1)ether solvent, 2) H3O+ ---> | 1* alcohol
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| Aldehyde + R-MgX --1)ether solvent, 2) H3O+ ---> | 2* alcohol
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| Ketone + R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 1 group added
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| acid chloride + 2R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 2 groups added
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| ester + 2R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 2 groups added
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| Ethylene Oxide + R-MgX --1)ether solvent, 2) H3O+ ---> | 1* alcohol, 2 carbons added
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| R-MgX + compound containing O-H, N-H, S-H, or terminal alkyne | protonated reagent + alkane
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| R-MgX + compound containing C=O, C=N, nitrile, S=O, N=O | will be attacked by reagent
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| 1* alcohol + Na(s) | alkoxide
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| 2* or 3* alcohol + K(s) | alkoxide
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| difficult alcohol + NaH in THF | alkoxide
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| Phenol + NaOH (aq) or KOH(aq) | phenoxide
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| Why doesnt a phenol need to be treated with Na or K metal to form a phenoxide? | Ion formation is favored due to resonance stabilization
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| aldehyde + 1)NaBH4, 2)H3O+ | 1* alcohol
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| ketone + 1)NaBH4, 2)H3O+ | 2* alcohol
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| carboxylic acid + 1)NaBH4, 2)H3O+ | no reaction, NaBH4 is selective
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| ester + 1)NaBH4, 2)H3O+ | no reaction, NaBH4 is selective
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| aldehyde + 1)LiAlH4, 2)H3O+ | 1* alcohol
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| ketone + 1)LiAlH4, 2)H3O+ | 2* alcohol
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| carboxylic acid + 1)LiAlH4, 2)H3O+ | 1* alcohol
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| ester + 1)LiAlH4, 2)H3O+ | 1* alcohol
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| alkene + 1)LiAlH4 | no reaction
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| alkene + NaBH4 | no reaction
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| aldehyde or ketone with double bonds + H2 --Raney Nickel--> | alcohol without double bonds
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| Na+-S-H + R-X | R-SH (thiol)
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| thiol + KMnO4 or HNO3 | sulfonic acid (has 2 other resonance forms)
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| R2CuLi(gilman reagent) +R'-X | R'-R + R-Cu + LiX
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| 2R-Li + CuI | R2CuI(gilman reagent formation) + LiI
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