(MCPBA)
CH2Cl2
MetaChloroPeroxyBenzoic Acid
50%
50%
Racemic Mixture of Enantiomers
“Reactive Peroxy Bond”
Syn Addition
Rainbow Guard Curved Arrow Mechanism
“Roche Hinge”
“Oh, the things you’ll do, for the love of making bonds.”
Is that “Roche Hinge”, made of Braavosi Gold!
Rainbow Guard? Never heard of them, I’ll ask my sister.
(Click “Slideshow” to Animate)
Major Product
Minor Product
Epoxide
Side Attacked
Less Sub. Attack
More Sub. Attack
Strong Nuc.
“Double Sided Electrophile”
“Inverts”
More Sub. Side, 3o
Less Sub.
Side, 2o
3o
Too much Steric Hindrance
No Rxn
H2O
Weak Elec.
(Ring Strain)
Major Product
Basic Conditions:
Just Attack!!
Dra-a-a-a-tik-tik!!
High Valyrian: Dracarys!!
English: Fire Attack!!
“Basic: Think - Charge Org. Intermediates”
Inverted
Less Sub.
Side, 2o
Neg. Ch. O. Intermed.
Inverted
“Basic: Think - Charge Org. Intermediates”
Major Product
Minor Product
Epoxide
Side Attacked
Less Sub. Attack
More Sub. Attack
Very Strong Nuc. / Base
“Double Sided Electrophile”
“Inverts”
More Sub. Side, 2o
Less Sub.
Side, 1o
Major Product
Basic Conditions:
Attack!!
1a.
b. H3O+(aq)
Weak Elec.
(Ring Strain)
Very Strong Nuc. / Base
Weak Elec.
(Ring Strain)
Minor Product
Ugh, Umph!
Not Stereocenters!
Hrrrrrr!
You call an Organolithium Strong!!
Oograa!!!
Basically Steric Hind. Dominates, I agree.
Inverted
“Acidic: Think + Charge Org. Intermediates”
Major Product
Minor Product
Epoxide
Side Attacked
Weak Elec.
Weak Nuc.
(TsOH)
More Sub. Attack
Less Sub. Attack
Strong Elec.
No Rxn
Weak Nuc.
Strong Elec.
Strong Elec.
Weak Nuc.
“Double Sided Electrophile”
“Inverts”
Major Product
Minor Product
Less Sub.
Side
Will React
Acidic Conditions:
One can’t always start with “Attack!!” as an opening, wit can also help you achieve your goals.
Yes! We need at least one Strong.
Tosic Acid, too powerful to retain its proton.
You’re showing promise in this, Game of Carbons.
More Sub. Side
Inverted
Inverted
Acidic Conditions
Basic Conditions
“Think - Charge
Org. Intermediates”
“Double Sided Electrophile”
(Except 3o, too much S.H.)
“Side Attacked Inverts”
“Think + Charge
Org. Intermediates”
“Double Sided Electrophile”
(1o, 2o & 3o)
Need at least one Strong Nuc. or Elec.
Start with, Attack!!
Start with, Protonation to make one strong.
Strong, Hahaha..
That is one thing, I am positive of.
The Grignard Adds under Basic Conditions, the Acid is added after the deed is done.
The LiAlH4 is very Basic, the Acid is added after the deed is done.
Negative? OK, I’ll subtract you!
You “Superior” High Lords, best keep your heads in your books. It don’t look as if a sword would fit well in your, pampered hand.
Actual Quiz on the following Slides
(Key above)
And here is a link to a Google Doc version of the Quiz.
Use colors for reacting electrons.
Acidic Conditions
Basic Conditions
“Think - Charge
Org. Intermediates”
“Double Sided Electrophile”
(Except 3o, too much S.H.)
“Side Attacked Inverts”
“Think + Charge
Org. Intermediates”
“Double Sided Electrophile”
(1o, 2o & 3o)
Need at least one Strong Nuc. or Elec.
Start with, Attack!!
Start with, Protonation to make one strong.