Polymerisation: Question 1

Syllabus 20.1

Multiple choice AS 1 mark

A section of an addition polymer chain is represented by the repeat unit

(CH2CH(CH(CH3)2))n\left(-\text{CH}_2-\text{CH}(\text{CH}(\text{CH}_3)_2)-\right)_n

Which alkene was used as the monomer to form this polymer?

Choose an answer to check it, then compare with the worked solution below.

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Worked solution

Step 1: Undo the addition polymerisation

In addition polymerisation, the C=C\text{C=C} double bond of the monomer opens up so that each carbon forms a new single bond to the next monomer unit, with no atoms lost. To find the monomer, reverse this process: take one repeat unit and turn the two backbone single bonds (the ones joining it to its neighbours) back into a double bond.

The given repeat unit is:

CH2CH(CH(CH3)2)-\text{CH}_2-\text{CH}(\text{CH}(\text{CH}_3)_2)-

Reconnecting the backbone carbons with a double bond gives:

CH2=CHCH(CH3)2\text{CH}_2=\text{CH}-\text{CH}(\text{CH}_3)_2

Step 2: Check the branching carefully

The backbone carbon that is not CH2-\text{CH}_2- carries exactly one branch, CH(CH3)2-\text{CH}(\text{CH}_3)_2 (an isopropyl group), plus one hydrogen atom. This matches a monomer with a single isopropyl branch on the carbon next to the terminal CH2=\text{CH}_2=. This is 3-methylbut-1-ene.

Why the other options are wrong

  • B (pent-1-ene) has a straight, unbranched chain, so its repeat unit would be CH2CH(CH2CH2CH3)-\text{CH}_2-\text{CH}(\text{CH}_2\text{CH}_2\text{CH}_3)-, a straight-chain propyl branch, not the branched isopropyl group shown.
  • C (2-methylbut-2-ene) is an internal alkene: both carbons of its double bond already carry alkyl groups, so neither backbone carbon in its polymer would be a plain, unsubstituted CH2-\text{CH}_2-. This does not match the given repeat unit.
  • D (2-methylbut-1-ene) puts the branch on the substituted backbone carbon itself, giving repeat unit CH2C(CH3)(CH2CH3)-\text{CH}_2-\text{C}(\text{CH}_3)(\text{CH}_2\text{CH}_3)-. A carbon with a methyl and an ethyl group and no hydrogen, which is different from the CH(CH(CH3)2)-\text{CH}(\text{CH}(\text{CH}_3)_2)- carbon (one hydrogen, one isopropyl branch) shown in the question.

Final answer

A, 3-methylbut-1-ene, CH2=CHCH(CH3)2\text{CH}_2=\text{CH}-\text{CH}(\text{CH}_3)_2.