Which initiator(s) can be used to polymerize each of the monomers?,

1. Consider the following initiators and monomers

Initiator Monomer
Grubbs initiator Propylene oxide
n-Butyl lithium Ɛ-Caprolactam
bpyNi(COD) Cyclooctene
BF3 + H2O Oxacyclobutane
H2SO4 δ-Valerolactone
NaOC2H5 NCA
H2O 1,5-Hexadiene
Octamethylcyclotetrasiloxane
Propylene Sulfide
Trioxane
Which initiator(s) can be used to polymerize each of the monomers?

Solution:
Cyclooctene: Propylene Sulfide:
Grubbs initiator n-Butyl lithium

Ɛ-Caprolactam:
Octamethylcyclotetrasiloxane:
H2O
n-Butyl lithium
H2SO4
NaOC2H5
1,5-Hexadiene:
Propylene Oxide: NaOC2H5
BF3 + H2O
δ-Valerolactone:
H2O
Oxacyclobutane:
H2SO4
n-Butyl lithium
NaOC2H5
NCA:
bpyNi(COD)
NaOC2H5

Trioxane:
Lewis acid &
Proton – base

, 2. Give the cyclic monomer(s), initiator, and reaction conditions necessary to synthesize each
of the following polymers:

a.




b.




c.


d.



e.



f.

Solution:

a. The anionic polymerization of δ-valerolactam produces polyamide 5 (nylon-5)
analogously to the homologous Ɛ-caprolactam.




Odd carbon number polyamides have ferroelectric properties and polarized films made
therefrom exhibit piezoelectric properties comparable to those of Polyvinylidene fluoride
(PVDF) and, in particular, make nylon 5 and its copolymers interesting for sensor
applications.