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This question is about six isomers of C8H16O2 - AQA - A-Level Chemistry - Question 10 - 2017 - Paper 2

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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+aO2bCO2+cH2OC_8H_{16}O_2 + aO_2 → bCO_2 + cH_2O

Where the stoichiometry needs to be balanced according to the combustion. To calculate the mass of P used, we first determine the moles of CO2CO_2 produced:

  1. Calculate moles of CO2CO_2: [ n_{ ext{CO}2} = \frac{V}{RT} = \frac{270 ext{ cm}³ imes 1 ext{ dm}³/1000 ext{ cm}³}{8.31 ext{ JK}^{-1} ext{mol}^{-1} imes 298 ext{ K}} ] [ n{ ext{CO}_2} = \text{value} ]

  2. 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:

Structure of T

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:

Repeating Unit of Polyester

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.

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