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HBr (alkene)
1.HBr
2.ROOR
(alkene)
1. H2SO4
2. H2O
(alkene)
Br2/CCl4
(alkene)
Br2/H2O
(alkene)
1. BH3
2. NaOH, H2O2
(alkene)
1) mCPBA
2) cat. H2SO4, H2O
(alkene)
1. Hg(OAc)2, H2O
2. NaBH4
(alkene)
1) OsO4
2) NaHSO3, H2O
(alkene)
1) O3
2) S(CH3)2 aka DMS
(alkene)
H2, Pt
(alkene)
1. Hg(OAc)2, ROH
2. NaBH4
(alkene)
H2, Lindlar's catalyst
(Alkyne)
Z Alkene
Na/NH3(l)
(Alkyne)
Alkyne to trans alkene.
HgSO4, H2SO4, H2O
(Alkyne)
carbonyl on more substituted carbon
1) HBR2 or 9-BBN
2) H2O2, NaOH
(Alkyne)
carbonyl on less substituted carbon
xs HBr
(Alkyne)
2 Br on more substituted carbon
xs Br2, CCl4
(Alkyne)
4 Br added to both ends of alkyne
HBr, ROOR
(alkyne)
2 Br on less substituted carbon
1) O3
2) H2O
(alkyne)
split too carboxylic acid and CO2
1) xs NaNH2 or xs LDA
2) H2O
creates terminal alkyne
NaNH2
depronating alkyne