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Chapter 22: Problem 7

Teflon is formed by a radical addition reaction involving the monomer tetrafluoroethylene. Show the mechanism for this reaction.

Short Answer

Expert verified
Teflon is formed from a radical addition reaction involving the monomer tetrafluoroethylene. The reaction mechanism involves three stages: initiation, propagation and termination. The initiation stage forms radical species using heat or light. The propagation stage involves the addition of these radicals to tetrafluoroethylene to form a radical intermediate and then a larger radical. The termination stage ends the chain reaction by forming Teflon from the radical species.

Step by step solution

01

Initiation

The initiation stage involves the formation of a radical species. This can be done using UV light or heat to break the bond of the initiator molecule, dichlorodifluoromethane (CCl2F2), into two radicals: CCl2F· and Cl· radicals. The reaction can be represented as follows: \[ \text{CCl}_2\text{F}_2 \rightarrow \text{CCl}_2\text{F}\cdot + \text{Cl}\cdot\]
02

Propagation

The propagation stage involves two reactions. In the first reaction, the Cl· radical interacts with the tetrafluoroethylene molecule, forming a radical intermediate. The second reaction involves the radical intermediate, reacting with another tetrafluoroethylene molecule, which forms a larger radical and regenerates a Cl· radical. These reactions can be represented as follows: \[ \text{Cl}\cdot + \text{C}_2\text{F}_4 \rightarrow \text{ClC}_2\text{F}_4\cdot\]\[ \text{ClC}_2\text{F}_4\cdot + \text{C}_2\text{F}_4 \rightarrow \text{ClC}_4\text{F}_8\cdot + \text{Cl}\cdot\]
03

Termination

The termination stage involves the reaction of two radical species to make a non-radical product. This reaction ends the radical chain reaction. In our case, two radical intermediates can collide and form the Teflon polymer. This reaction can be represented as follows: \[ 2\text{ClC}_4\text{F}_8\cdot \rightarrow \text{Cl}_2\text{C}_4\text{F}_8\] The final product, Teflon, is formed.

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