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Jacob McNamara Elmhurst College, Elmhurst, Illinois. Problems with the old synthesis: -Originally produced for acetaldehyde -this was expensive due to the high temp. combustions of light hydrocarbons -28 cents per pound was the cost Solution to this problem:

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wacker process

Jacob McNamara

Elmhurst College, Elmhurst, Illinois

Problems with the old synthesis:

-Originally produced for acetaldehyde

-this was expensive due to the high

temp. combustions of light hydrocarbons

-28 cents per pound was the cost

Solution to this problem:

-Started with ethylene, which only costs 3.5 cents per pound

Wacker Process

Step 1

+

PdCl4 reacts with ethylene to form PdCl3 with a bond connecting to the bond of H2C=CH2

Old Initial Synthesis of Olefins

Used mainly in the oil industry

Step 2

+

Detailed Mechanism for Step 4

This palladium complex reacts with water to eject a chlorine atom

New Synthesis of Olefins:

Replace a hydrogen on the ethylene molecule with

the desired ligand by a basic substitution reaction.

Step 3

+

Based on the HOMO diagram below, another molecule of water attacks the pi-bond

on the ethylene portion of the molecule, causing a CH2CH2OH chain to form.

The palladium catalyst is regenerated

by a reaction with CuCl2

Detailed

Mechanism

Step 4

Refer to the mechanism to the right for how this reaction takes place

Metal-olefin complexes use back-bonding

- this means there is a decrease in electron density

of the pi-bonding orbital of the olefin and a gain

of electron density in the pi-star orbital.

Step 5

A molecule of water comes, and its lone pair takes the hydrogen atom off of the oxygen,

which gives the final product, plus some hydronium ions.