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3. Discuss the effect of diffusion-controlled reactions on reactivity of macromolecules.
4. Discuss how paired group and neighboring group effects influence random irreversible reactions.
5. Discuss reactions that favor large molecules.
Section 9.2
1. Explain, showing chemical equations, how hydrochlorination of natural
rubber
is often
accompanied by cyclization.
2. Discuss chlorination of natural rubber. How can natural rubber and polybutadiene be brominated?
3. Discuss with the aid of chemical equations hydrogenation of 1,4-polybutadiene.
4. How can polyisoprene and polybutadiene be modified by additions of carbenes? Explain and
discuss, showing the structures of the starting materials and the products.
5. Illustrate the Prins reactions of rubber with formaldehyde and with glyoxal. How can this reaction
be carried out in the solid phase?
6. Discuss polar additions to unsaturated polymers. Give examples Include the
ene
reaction.
7. How can the Ritter reactions be carried out on isoprenes?
8. How can the Diels-Alder reactions are carried out with unsaturated polymers. Use chemical
equations to illustrate.
9. Explain how polybutadiene and isoprene can be epoxidized, giving reagents and showing all
by-products.
Section 9.3
1. Show how, and explain why, cis -polybutadiene rearranges to trans as a result of irradiation by
gamma rays or ultraviolet light. Also, show what happens to polyisoprene when it is irradiated in
the ultraviolet light.
2. Discuss with the aid of chemical equations the cyclization reactions of rubber.
3. How are polyacrylonitrile fibers converted to graphite-like fibers. Explain, showing all the steps in
thermal cyclization of polyacrylonitrile.
4. Discuss migration of double bonds in polymers.
5. How does poly(4,4 0 -diphenylpropane isophthalate) rearrange upon irradiation with ultraviolet
light?
6. Give examples of the Schmidt and Beckmann rearrangements.
Section 9.4
1. Discuss with the help of chemical equations the fluorination reactions of polyethylene.
2. Discuss chlorination of polyethylene and polypropylene.
3. How is chlorosulfonation of polyethylene carried out industrially. Explain and write the chemical
equations for the reactions. How is the product used?
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