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Multiple Choice
Which of the following monomers will show the greatest selectivity for head-to-tail addition?
A
prop-1-ene
B
(E)-but-2-ene
C
2-methylprop-1-ene
D
None of these.
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1
Identify the structure of each monomer: prop-1-ene, (E)-but-2-ene, and 2-methylprop-1-ene. Note the position of the double bond and any substituents attached to the carbon atoms involved in the double bond.
Understand the concept of head-to-tail addition in polymer chemistry, where the head of one monomer (the more substituted end of the double bond) reacts with the tail of another monomer (the less substituted end).
Analyze the substituents on the double-bonded carbons for each monomer. The greater the difference in substitution between the two carbons, the more selective the monomer will be for head-to-tail addition.
For prop-1-ene, the double bond is between a primary and a secondary carbon. For (E)-but-2-ene, the double bond is between two secondary carbons. For 2-methylprop-1-ene, the double bond is between a tertiary and a primary carbon.
Determine which monomer has the greatest difference in substitution between the two carbons of the double bond. 2-methylprop-1-ene, with a tertiary and a primary carbon, will show the greatest selectivity for head-to-tail addition due to the significant difference in substitution.