Green Oxidation

Whats the premise of Green Oxidation lab

Using a Cu-based reeaction to catalyze the oxidation of a primary alochol to a aldehyde

In what conditions did the Green oxidation lab take place

In Aerobic conditions (the presence of oxygen)

What ion Cu did we use

Copper (I)

Why did we choose Copper over OsO4

OsO4 is highly Toxic

Why did we choose Copper over CrO3
(Cr(IV))

Chromium is bad for the enviorment and hard to dispose it

What are some metals that we typically see oxidize reactions

OsO4, Cro3 in conc. H2SO4, KMnO4, and PCC

What does PCC stand for

Pyridinium chlorochromate

Why are the oxidative agents that I just noted bad

We need the same mol amount of reactant that needs to be oxidize (though they are catalyze we need alot)
It yeilds by inorganic salts as by products that requires an additional seperative step
They promote over oxidation, we just want an aldehyde not a carboxylic acid

What is the definition of a catalyst

An additive used in sub-stiochiometric amount that increase the rate of reaction without itsefl being consumed or undergoing a net chemical change

How does a catalyst increase the rate of reaction

lowers the activation energy process, mean there is a change of the energy at the transition state

What is the EXACT catalyst molecule (all)

Copper (I) Bromide
2,2-bipyridine (bpy)
N-methyl; imidazole (NMI)
TEMPO

Tell me the reaction of this lab

CuBr+NMPI+BPY form this big catalytic group which then associates with TEMPOH
this group gets oxdized by the use of ½ O2 and H2O to go from a red/brown color to a green color

In this oxidization reacction Copper 1 turns into copper 2 by adding an OH to it the Oxygen came from the ½ O2 and the H came from TEMPOH to become TEMPO

Then this green group oxidize a benzyl alcohol to an benzaldehyde and releases H2O to go back to it’s orginal red/brown color

Summary: What gets reduced

TEMPO and Cu(II) in the coordinated complex

Summary: What gets oxidized

TEMPOH and Cu(I) in the coordinated complex

Give me the stichiometric reaction of this lab

ArCH₂OH + ½ O₂ → ArCHO + H2O

What does TEMPO Stand for

2,2,6,6-Tetramehyl-1piperidinyloxyl

Attached are 4 molecules what gets reduced and what gets oxidized

The red/brown molecule gets oxdized
The Green molecule gets reduced

Is Copper Bromide dense

Yes!

Based on the American Chemical Society “Green

Chemistry Institute”, how does this reaction conform to the principles of green

chemistry?

Prevention of waste in compirson of other reagents
highly atom-econimical
Less hazard chemical substance in comparison to other metal catalyst

things to ask

What part of the reaction are we supposed to know (ask about the top of page 2)
What Hazards should we know
What part of the procedure should we know, will it ask why specific reagents

How did we know the reaction is complete

When an solution turned green and a color change was seen

Why did we use nitrogen to evaporate at the end

So iwe can remove our solvent (pentane) and it’s a safe way

In the lab we did a liquid-liquid extraction which layer is which

The top layer will be the organic layer because the pentane solvent is less dense than water.

What was the main hazard we needed to look out for and what was it’s hazard

Acetone and pentane, they are flammable