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The outer layers of some golf balls are made from a polymer called polyisoprene - AQA - A-Level Chemistry - Question 3 - 2019 - Paper 2

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The outer layers of some golf balls are made from a polymer called polyisoprene. The isoprene monomer is a non-cyclic branched hydrocarbon that contains 88.2 % carbo... show full transcript

Worked Solution & Example Answer:The outer layers of some golf balls are made from a polymer called polyisoprene - AQA - A-Level Chemistry - Question 3 - 2019 - Paper 2

Step 1

Deduce the molecular formula and suggest a possible structure.

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Answer

To deduce the molecular formula, we start with the empirical formula. Given that the empirical formula of isoprene is the same as its molecular formula, we can conclude:

The empirical formula can be calculated based on the percentage of carbon: 88.2% carbon implies that the remaining percentage is hydrogen:

Assuming 100 g of isoprene:

  • Mass of Carbon = 88.2 g
  • Mass of Hydrogen = 100 g - 88.2 g = 11.8 g

Next, we calculate the number of moles:

  • Moles of Carbon = 88.2 g / 12.01 g/mol = 7.35 mol
  • Moles of Hydrogen = 11.8 g / 1.008 g/mol = 11.8 mol

We take the smallest number of moles, which is 7.35, and divide both by 7.35:

  • C = 7.35 / 7.35 = 1
  • H = 11.8 / 7.35 = 1.6

To get whole numbers, we multiply by 5:

  • C = 5
  • H = 8

Therefore, the molecular formula is C₅H₈. A possible structure is the branched form:

   H   H
    \ /
     C
    / \ 
   H   C - H
      /   \
    H     H

This represents 2-methyl-1,3-butadiene.

Step 2

Draw the skeletal formula of the monomer used to make this polymer.

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Answer

The skeletal formula of the monomer is:

   H   H
    \ /
     C
    / \ 
   H   C - H
      /   \
    C = C
    / \ 
   H   H

IUPAC name of the monomer is 1,3-butadiene.

Step 3

A second polymer in the mixture has a repeating unit with the structure shown.

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Answer

The repeating unit shown is a simple polymer structure derived from 1,3-butadiene. The structure would be:

   -C=C-
     /  \  
   H    H  

The repeating units can connect in this vinyl fashion.

Step 4

Draw the structure of the repeating unit of the third polymer.

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Answer

The repeating unit of the third polymer can be drawn as:

   -C=C-
     /  \  
    H    H  

This polymer represents the trans configuration of 1,3-butadiene causing stereoisomerism.

Step 5

Give a reason why this type of stereoisomerism arises.

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Answer

Stereoisomerism arises due to restricted rotation around the C=C double bond. This restriction allows for the occurrence of cis and trans configurations, resulting in different spatial arrangements of the substituents attached to the double-bonded carbons.

Step 6

Explain why these golf balls do not biodegrade.

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Answer

Golf balls do not biodegrade because they are made from synthetic polymers like polyisoprene that are chemically stable and resistant to microbial degradation. Carbon-carbon bonds in these polymers are non-polar and not easily attacked by water or reactive chemicals in the environment, which makes them durable and long-lasting.

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