Dirty HBr
Sticks Br onto the wrong side. Only HBr works because of energy balance.

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Dirty HBr
Sticks Br onto the wrong side. Only HBr works because of energy balance.
Hydrogenation of Alkene using Pd(C)
Syn addition
Ozonolysis
Ozone + Zn/H2O2 Cleaves Alkenes
Creating a Cis Diol using OsO4
can use SOBr2 or SOCl2 to turn the diol to other
Can form oxiranes from MCPBA or Dimethyl Dioxirane (As my professor fondly calls it, "Spectacles")
Reverse Regioselectivity. Put the H on the "wrong atom"
BH3 is really BH3THF
if use NH2-OSO3 instead of HOOH, can get amine
In order to stop rearrangement, we need to bridge.
Use Hg(OAc)+ to act as a bridge, cleaved off by BH4-
Stereoselective, Anti attack
Hydride Shift occurs with H+ because it does not bridge
Rearrangement will only go down to more stability
We get polymerization in dilute conditions of nucleophile or if there are no other good nucleophiles, then the alkene acts as the nucleophile.
Formation of a ring can also happen
H does not bridge, thus, not need to worry as much on stereochemistry
H+HSO4 HSO4- is not a good nucleophile , so will not attack again
same with H+ClO4
Br2 can also attack from the top to get the SS enantiomer
We can't get Chiral Products from achiral reactant, so the product ends up being a racemic mixture
The "I suspect rule":
if Ionic/small, "hard", prefer attack C=O
S, I reversible
if Covalent/big, "squishy", prefer attack C=C
if covalent attack C=O, it's reversible b/c weaker base
F, O reversible
BH4- and AlH4- don't care
Diols are in Equilibrium with their corresponding Ketone
//Laughs nervously
Reductive Amination