Youyou's Organic Chemistry Notes

Hi, reactions from introductory Organic Chem. I use this mainly for tumblr's tagging system which makes it easy to sort through reactions. As of the 2013-2014 school year, I have no more plans to take another orgo course. Thus, this blog will no longer be updated. Consider this a good reference/archived tool.

[myorgonotes]

Dirty HBr

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

[myorgonotes]

Hydrogenation of Alkene using Pd(C)

Syn addition

[myorgonotes]

Ozonolysis

Ozone + Zn/H2O2 Cleaves Alkenes

[myorgonotes]

Creating a Cis Diol using OsO4

can use SOBr2 or SOCl2 to turn the diol to other

[myorgonotes]

Can form oxiranes from MCPBA or Dimethyl Dioxirane (As my professor fondly calls it, "Spectacles")

[myorgonotes]

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

BH3 is really BH3THF

if use NH2-OSO3 instead of HOOH, can get amine

[myorgonotes]

In order to stop rearrangement, we need to bridge.

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

Stereoselective, Anti attack

[myorgonotes]

Hydride Shift occurs with H+ because it does not bridge

Rearrangement will only go down to more stability

[myorgonotes]

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

[myorgonotes]

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

[myorgonotes]

[myorgonotes]

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

[myorgonotes]

[myorgonotes]

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

[myorgonotes]

Diols are in Equilibrium with their corresponding Ketone

[myorgonotes]

//Laughs nervously

[myorgonotes]

Reductive Amination