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UB CHE 201 Ch 10 A
Alcohol Synthesis(New Reactions). Given Reactant and Reagent Give Product
| Question | Answer |
|---|---|
| R-X + Mg ---ether--> | R-Mg-X, grignard reagent |
| R-X + 2Li ---> | R-Li(organolithium reagent) + Li+-X |
| Formaldehyde + R-MgX --1)ether solvent, 2) H3O+ ---> | 1* alcohol |
| Aldehyde + R-MgX --1)ether solvent, 2) H3O+ ---> | 2* alcohol |
| Ketone + R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 1 group added |
| acid chloride + 2R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 2 groups added |
| ester + 2R-MgX --1)ether solvent, 2) H3O+ ---> | 3* alcohol, 2 groups added |
| Ethylene Oxide + R-MgX --1)ether solvent, 2) H3O+ ---> | 1* alcohol, 2 carbons added |
| R-MgX + compound containing O-H, N-H, S-H, or terminal alkyne | protonated reagent + alkane |
| R-MgX + compound containing C=O, C=N, nitrile, S=O, N=O | will be attacked by reagent |
| 1* alcohol + Na(s) | alkoxide |
| 2* or 3* alcohol + K(s) | alkoxide |
| difficult alcohol + NaH in THF | alkoxide |
| Phenol + NaOH (aq) or KOH(aq) | phenoxide |
| 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 |
| aldehyde + 1)NaBH4, 2)H3O+ | 1* alcohol |
| ketone + 1)NaBH4, 2)H3O+ | 2* alcohol |
| carboxylic acid + 1)NaBH4, 2)H3O+ | no reaction, NaBH4 is selective |
| ester + 1)NaBH4, 2)H3O+ | no reaction, NaBH4 is selective |
| aldehyde + 1)LiAlH4, 2)H3O+ | 1* alcohol |
| ketone + 1)LiAlH4, 2)H3O+ | 2* alcohol |
| carboxylic acid + 1)LiAlH4, 2)H3O+ | 1* alcohol |
| ester + 1)LiAlH4, 2)H3O+ | 1* alcohol |
| alkene + 1)LiAlH4 | no reaction |
| alkene + NaBH4 | no reaction |
| aldehyde or ketone with double bonds + H2 --Raney Nickel--> | alcohol without double bonds |
| Na+-S-H + R-X | R-SH (thiol) |
| thiol + KMnO4 or HNO3 | sulfonic acid (has 2 other resonance forms) |
| R2CuLi(gilman reagent) +R'-X | R'-R + R-Cu + LiX |
| 2R-Li + CuI | R2CuI(gilman reagent formation) + LiI |
Created by:
HugsAndKisses
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