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7 Organic chemistry

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Question 46

A polymer chemist studies two reactions, P and Q. The table gives information about the starting molecules and one repeating unit of each polymer.

ReactionStarting molecule(s)Functional group informationFormula of one repeating unit
POne molecule with formula C4H8\text{C}_4\text{H}_8C4​H8​Contains a C=C\text{C}=\text{C}C=C bondC4H8\text{C}_4\text{H}_8C4​H8​
QMolecule X, C4H10O2\text{C}_4\text{H}_{10}\text{O}_2C4​H10​O2​, and molecule Y, C2H2O4\text{C}_2\text{H}_2\text{O}_4C2​H2​O4​X has an OH\text{OH}OH group at each end; Y has a COOH\text{COOH}COOH group at each endC6H8O4\text{C}_6\text{H}_8\text{O}_4C6​H8​O4​

A chemist considers two candidates to replace X in reaction Q.

CandidateStructure
AHO-CH2-CH2-OH\text{HO-CH}_2\text{-CH}_2\text{-OH}HO-CH2​-CH2​-OH
BCH3-CH2-OH\text{CH}_3\text{-CH}_2\text{-OH}CH3​-CH2​-OH
a.

Explain, using the data, why one repeating unit from reaction P contains the same atoms as its monomer but one repeating unit from reaction Q does not. Use the formulae to determine the number of water molecules equivalent to the atoms missing from one repeating unit of Q.

[4]
b.

Which candidate could replace X while allowing reaction Q to form a long polymer chain? Justify your choice using the structures.

[2]
Markscheme

7 Organic chemistry Questions

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