This question is about six isomers of C8H16O2 - AQA - A-Level Chemistry - Question 10 - 2017 - Paper 2
Question 10
This question is about six isomers of C8H16O2.
1. Give the full IUPAC name of isomer P.
CH3CH2C(COOH)(CH3)
2. A sample of P was mixed with an excess of oxygen... show full transcript
Worked Solution & Example Answer:This question is about six isomers of C8H16O2 - AQA - A-Level Chemistry - Question 10 - 2017 - Paper 2
Step 1
Give the full IUPAC name of isomer P.
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Answer
The full IUPAC name of isomer P is 2-methyl-2-(3-carboxypropyl)acetic acid.
Step 2
Write an equation for the combustion of P in an excess of oxygen and calculate the mass, in mg, of P used.
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Answer
The combustion equation for isomer P can be written as:
C8H16O2+aO2→bCO2+cH2O
Where the stoichiometry needs to be balanced according to the combustion. To calculate the mass of P used, we first determine the moles of CO2 produced:
Calculate moles of P:
Given the stoichiometry in typical combustion, find the mass using the molar mass of P.
Step 3
Use these spectra and Tables A and C in the Data Booklet to deduce the structure of Q. In your answer, state one piece of evidence you have used from each spectrum.
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Answer
The structure of Q can be identified as 3-hydroxybutanoic acid. Evidence from Figure 4 indicates a distinct peak pattern, while Figure 5 shows specific carbon environments consistent with this structure.
Step 4
Justify this statement using Table C from the Data Booklet. Give the number of peaks for each isomer.
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Answer
R has 5 peaks because each carbon environment is unique. In contrast, S features overlap in its carbon environments resulting in 4 peaks overall, confirming the statement.
Step 5
Justify this statement using the splitting patterns of the peaks. Give the number of peaks for each isomer.
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Answer
For R, we observe a triplet and a quartet in its 1H spectrum which indicates non-equivalent environments. S, however, displays only singlets, allowing for clear differentiation. R has 3 peaks whereas S has 2 peaks in this splitting analysis.
Step 6
Draw the structure of T.
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Answer
The structure of T is shown as a cyclic compound resulting from dehydration of 5-hydroxyhexanoic acid, depicted as follows:
Step 7
Draw the repeating unit of the polyester.
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Answer
The repeating unit of the polyester formed by 5-hydroxyhexanoic acid can be represented as follows:
Step 8
Justify the statement that, although both polymer structures contain ester groups, the polymer formed by U is not biodegradable.
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Answer
The polymer formed by U lacks the chemical groups needed for hydrolysis under environmental conditions, whereas the ester groups in the other polymer are more susceptible to enzymatic attack.