PROBLEM 26.12 Polyphthalamides are a class of polymers used in several components of automobile engines, and are produced using benzene-1,4-dioic acid and an aliphatic diamine. Draw the repeating unit for the polyphthalamide that uses hexane-1,6-diamine. NH2 HO, H,N НО Hexane-1,6-diamine Benzene-1,4-dioic acid SOLVED PROBLEM 26.11 Kevlar is a high-strength polymer used in body armor and bicycle tires. It is a condensation polymer synthesized from benzene-1,4-diamine (para-phenylenediamine) and benzene-1,4-dicarbonyl chloride (terephthaloyl chloride). Draw the repeating unit for Kevlar. NH2 H,N Benzene-1,4-diamine (para-Phenylenediamine) Benzene-1,4-dicarbonyl chloride (Terephthaloyl chloride) Think What functional group does benzene-1,4-diamine contain? What functional group does benzene-1,4-dicarbonyl chloride contain? When those functional groups react, what functional group is produced? Does that product contain other reactive sites for polymerization to continue? Solve Benzene-1,4-diamine has an NH2 functional group and benzene-1,4- dicarbonyl chloride has a COCI functional group. We learned in Section 21.3 that molecules with these functional groups react to produce an amide that connects the two molecules together, so these two monomers will produce a dimer. NH2 CI N. H,N H,N

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Which polymer do you think has the higher Tg, Kevlar (see Solved Problem 26.11) or the polyphthalamide described in Problem 26.12 (p. 1328)? Explain your reasoning.

PROBLEM 26.12 Polyphthalamides are a class of polymers used in several
components of automobile engines, and are produced using benzene-1,4-dioic acid
and an aliphatic diamine. Draw the repeating unit for the polyphthalamide that uses
hexane-1,6-diamine.
NH2
HO,
H,N
НО
Hexane-1,6-diamine
Benzene-1,4-dioic acid
Transcribed Image Text:PROBLEM 26.12 Polyphthalamides are a class of polymers used in several components of automobile engines, and are produced using benzene-1,4-dioic acid and an aliphatic diamine. Draw the repeating unit for the polyphthalamide that uses hexane-1,6-diamine. NH2 HO, H,N НО Hexane-1,6-diamine Benzene-1,4-dioic acid
SOLVED PROBLEM 26.11
Kevlar is a high-strength polymer used in body armor and bicycle tires. It is a
condensation polymer synthesized from benzene-1,4-diamine (para-phenylenediamine)
and benzene-1,4-dicarbonyl chloride (terephthaloyl chloride). Draw the repeating unit
for Kevlar.
NH2
H,N
Benzene-1,4-diamine
(para-Phenylenediamine)
Benzene-1,4-dicarbonyl chloride
(Terephthaloyl chloride)
Think What functional group does benzene-1,4-diamine contain? What functional
group does benzene-1,4-dicarbonyl chloride contain? When those functional groups
react, what functional group is produced? Does that product contain other reactive
sites for polymerization to continue?
Solve Benzene-1,4-diamine has an NH2 functional group and benzene-1,4-
dicarbonyl chloride has a COCI functional group. We learned in Section 21.3 that
molecules with these functional groups react to produce an amide that connects
the two molecules together, so these two monomers will produce a dimer.
NH2
CI
N.
H,N
H,N
Transcribed Image Text:SOLVED PROBLEM 26.11 Kevlar is a high-strength polymer used in body armor and bicycle tires. It is a condensation polymer synthesized from benzene-1,4-diamine (para-phenylenediamine) and benzene-1,4-dicarbonyl chloride (terephthaloyl chloride). Draw the repeating unit for Kevlar. NH2 H,N Benzene-1,4-diamine (para-Phenylenediamine) Benzene-1,4-dicarbonyl chloride (Terephthaloyl chloride) Think What functional group does benzene-1,4-diamine contain? What functional group does benzene-1,4-dicarbonyl chloride contain? When those functional groups react, what functional group is produced? Does that product contain other reactive sites for polymerization to continue? Solve Benzene-1,4-diamine has an NH2 functional group and benzene-1,4- dicarbonyl chloride has a COCI functional group. We learned in Section 21.3 that molecules with these functional groups react to produce an amide that connects the two molecules together, so these two monomers will produce a dimer. NH2 CI N. H,N H,N
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