Polymers Basic
Polymers Basic
14. Identify the monomer units from which each of the following polymers is made, and tell
whether each is a chain-growth or a step-growth polymer.
17. Show the structure of the polymer that results from heating the following diepoxide and
diamine:
23. Nitroethylene, H2C=CHNO2, is a sensitive compound that must be prepared with great
care. Attempted purification of nitroethylene by distillation often results in low recovery of
product and a white coating on the inner walls of the distillation apparatus. Explain.
24. Poly(vinyl butyral) is used as the plastic laminate in the preparation of automobile
windshield safety glass. How would you synthesize this polymer?
25. What is the structure of the polymer produced by anionic polymerization of β-propiolactone
using NaOH as catalyst?
26. Glyptal is a highly cross-linked thermosetting resin produced by heating glycerol and
phthalic anhydride (1,2-benzenedicarboxylic acid anhydride). Show the structure of a
representative segment of glyptal.
27. Melmac, a thermosetting resin often used to make plastic dishes, is prepared by heating
melamine with formaldehyde. Look at the structure of Bakelite shown in Section 31.5, and then
propose a structure for Melmac.
28. Epoxy adhesives are cross-linked resins prepared in two steps. The first step involves SN2
reaction of the disodium salt of bisphenol A with epichlorohydrin to form a low-molecular-
weight prepolymer. This prepolymer is then “cured” into a cross-linked resin by treatment with
a triamine such as H2NCH2CH2NHCH2CH2NH2.
32. The polymeric resin used for Merrifield solid-phase peptide synthesis (Section 26.8) is
prepared by treating polystyrene with N-(hydroxymethyl)phthalimide and
trifluoromethanesulfonic acid, followed by reaction with hydrazine. Propose a mechanism for
both steps.