OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
Chapter 31 – Synthetic Polymers
Solutions to Problems
31.1
The alkenes most reactive to cationic polymerization contain electron-donating functional
groups that can stabilize the carbocation intermediate. The reactivity order of substituents
in cationic polymerization is similar to the reactivity order of substituted benzenes in
electrophilic aromatic substitution reactions.
31.2
Anionic polymerization occurs most readily with alkenes having electron-withdrawing
substituents.
31.3
The intermediate anion can be stabilized by resonance involving the phenyl ring.
31.4
Vinylidene chloride doesn’t polymerize in isotactic, syndiotactic or atactic forms because
no asymmetric centers are formed during polymerization.
31.5 None of the polypropylenes rotate plane-polarized light. If an optically inactive reagent
and an achiral compound react, the product must be optically inactive. For every chirality
center generated, an enantiomeric chirality center is also generated, and the resulting
polymer mixture is optically inactive.
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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
31.6
31.7
Irradiation homolytically cleaves an allylic C–H bond because it has the lowest bond
energy. The resulting radical adds to styrene to produce a polystyrene graft.
31.8
31.9
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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
31.10
Vestenamer can be formed by an ADMET synthesis using 1,9-decadiene.
Vestenamer is usually synthesized from cyclooctene by a ROMP polymerization.
Norbornene undergoes ROMP polymerization to yield Norsorex.
31.11
The product of hydrogenation of natural rubber is atactic. This product also results from
the radical copolymerization of propene with ethylene.
3 10/27/2023
Chapter 31 – Synthetic Polymers
Solutions to Problems
31.1
The alkenes most reactive to cationic polymerization contain electron-donating functional
groups that can stabilize the carbocation intermediate. The reactivity order of substituents
in cationic polymerization is similar to the reactivity order of substituted benzenes in
electrophilic aromatic substitution reactions.
31.2
Anionic polymerization occurs most readily with alkenes having electron-withdrawing
substituents.
31.3
The intermediate anion can be stabilized by resonance involving the phenyl ring.
31.4
Vinylidene chloride doesn’t polymerize in isotactic, syndiotactic or atactic forms because
no asymmetric centers are formed during polymerization.
31.5 None of the polypropylenes rotate plane-polarized light. If an optically inactive reagent
and an achiral compound react, the product must be optically inactive. For every chirality
center generated, an enantiomeric chirality center is also generated, and the resulting
polymer mixture is optically inactive.
1 10/27/2023
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
31.6
31.7
Irradiation homolytically cleaves an allylic C–H bond because it has the lowest bond
energy. The resulting radical adds to styrene to produce a polystyrene graft.
31.8
31.9
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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
31.10
Vestenamer can be formed by an ADMET synthesis using 1,9-decadiene.
Vestenamer is usually synthesized from cyclooctene by a ROMP polymerization.
Norbornene undergoes ROMP polymerization to yield Norsorex.
31.11
The product of hydrogenation of natural rubber is atactic. This product also results from
the radical copolymerization of propene with ethylene.
3 10/27/2023
