O Chem Rxn Flashcards
Halohydrin Formation
X2 over H2O. Adds an X and an OH. Halogen ion intermediate. S: anti R: Markovnikov, OH preferring higher substituted C
Addition of HX to Alkenes
Adds H and X.
S: N/A
R: Markovnikov
Acid Catalyzed Alkene Hydration
Adds H and OH.
Water removes proton, water is deprotonated, water joins molecule, water is deprotonated.
R: Mark, but not consistent since shifts are possible.
Oxymercuration of Alkenes
Adds H and OH.
S: anti
R: Markovnikov
- Hg(OAC)2, H2O/THF
- NaBH4
(Compare to hydroboration)
Hydroboration of Alkenes
Adds H and OH
S: Syn
R: non-Markovnikov
1. BH3/THF
2. H2O2, NaOH, H2O
(compare to oxymercuration)
Dichlorocarbene Addition
Forms cyclopropane with Halogens attached.
S:Syn
R: NA
CHCl3, KOH
(compare to Simmons-Smith)
Simmons-Smith
Forms cyclopropane without attached Halogens.
S: Syn
R: NA
CH2I2, Zn(Cu), ether
(compare to Dichlorocarbene addition)
Catalytic hydrogenation of Alkenes
Adds two H.
S: Syn
R: NA
H2, Pd/C or PtO2
Peroxyacid Epoxidation
Peroxyacid forms epoxide from Alkene. Acid adds 2 OH
S: anti
R: NA
- Peroxyacid
2 H3O+
(acid step mimics X2 addition)
(compare result to OsO4 hydroxylation)
Hydroxylation with Osmium Tetraoxide
Adds 2 OH.
S: Syn
R: NA
- OsO4, pyridine
- NaHSO3, H2O
(compare to epoxide hydrolysis)
Oxidative Cleavage of Alkenes with Ozone
Splits DBs with DB Os.
- O3
- Zn, H3O+
Oxidative Cleavage of Alkenes with Potassium Permanganate
Splits DBs with DB Os.
R groups stay, 1 H becomes OH, 2 H becomes CO2.
KMnO4, H3O+
Bromohydrin Formation
Adds Br and OH.
Anti, Markovnikov.
NBS in H2O with DMSO.
Dehydrohalogenation of Vicinal Dihydrides
Forms alkyne from alkane.
2 KOH, ethanol
Or 2 NaNH2, NH3
Addition of HCl or HBr to alkynes
Markovnikov, usually trans. 2nd equivalent, Xs on same C.