synthetic transformations

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32 Terms

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8.1 Oxymercuration-demercuration
1) Hg(OAc)2, H2O 2) NaBH4 | Markovnikov H + OH, no rearrangement
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8.2 Alkoxymercuration-demercuration
1) Hg(OAc)2, HOR 2) NaBH4 | Markovnikov H + OR (ether), no rearrangement
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8.3 Anti-Markovnikov H + OH
1) BH3, THF 2) H2O2, NaOH
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8.4 Anti-Markovnikov H + Br
HBr, peroxides (ROOR), heat/light
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8.5 Markovnikov H + X
HX, cold, dark, no peroxides
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9.1 Br2 + alkene
Anti addition: trans only
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9.2 Alkene to epoxide
MCPBA (peroxy acid)
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9.3 Epoxide opening, basic
1) strong Nu (RO-, R2N-) 2) dilute acid | Nu attacks LESS hindered C
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9.4 Epoxide opening, acidic
HOR + acid | Nu attacks MORE substituted C
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9.5 Br2 + HOR + alkene
Br on less substituted C, OR on more substituted C (anti)
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9.6 Cyclopropane from alkene
Carbene: CHCl3 + KOH (:CCl2) or CH2I2 + Zn(Cu) (:CH2)
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10.1 Hydroboration-oxidation
1) BH3 2) H2O2, NaOH | Syn, anti-Markovnikov
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10.2 Catalytic hydrogenation (alkene)
H2, Pt or Pd | Syn addition
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10.3 Alkyne to alkane
H2, Pt or Pd
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10.4 Alkyne to cis alkene
H2/Lindlar catalyst (or H2/Ni2B)
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10.5 Alkyne to trans alkene
Na metal, NH3(l)
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10.6 1° alcohol to aldehyde
PCC
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10.7 2° alcohol to ketone
KMnO4, Na2Cr2O7/acid, CrO3/acid, or PCC
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10.8 1° alcohol/aldehyde to carboxylic acid
KMnO4, Na2Cr2O7/acid, or CrO3/acid (not PCC)
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10.9 Syn dihydroxylation
OsO4, then H2O2 or NaHSO3 | (cold dilute KMnO4, then KOH, also works)
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10.10 Ozonolysis
1) O3 2) Zn, acetic acid | C=C becomes two C=O
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10.11 Permanganate cleavage of C=C
1) hot KMnO4 2) H3O+ | C-H carbon becomes COOH
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11.1 HX + terminal alkyne
HX, dark, cold. 1 equiv: vinyl halide; excess: geminal dihalide
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11.2 X2 + alkyne
1 equiv: dihaloalkene; excess: tetrahaloalkane
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11.3 Markovnikov hydration of alkyne
H2O, H2SO4, HgSO4 | Product: methyl ketone
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11.4 Anti-Markovnikov hydration of alkyne
1) BH3, THF 2) H2O2, NaOH | Product: aldehyde
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11.5 Deprotonate terminal alkyne
NaNH2 | Product: acetylide anion
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11.6 Nitrile hydrolysis
H2O, H2SO4 | Product: carboxylic acid
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Cis vs. trans alkyne reduction
Lindlar gives cis; Na/NH3 gives trans
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PCC vs. strong oxidant on 1° alcohol
PCC: aldehyde. KMnO4/dichromate/CrO3: carboxylic acid
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Alkyne hydration: ketone vs. aldehyde
Hg/acid: ketone. Borane: aldehyde
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Epoxide opening: acid vs. base
Acid: more substituted C. Base: less hindered C