Youyou's Organic Chemistry Notes

Dirty HBr

Hydrogenation of Alkene using Pd(C)

Ozonolysis

Creating a Cis Diol using OsO4

Reverse Regioselectivity. Put the H on the "wrong atom"

BH3 is really BH3THF

In order to stop rearrangement, we need to bridge.

Use Hg(OAc)+ to act as a bridge, cleaved off by BH4-

Hydride Shift occurs with H+ because it does not bridge

We get polymerization in dilute conditions of nucleophile or if there are no other good nucleophiles, then the alkene acts as the nucleophile. 

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

Br2 can also attack from the top to get the SS enantiomer

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