SPS F108 12.1_Carbonyl Compounds, Carboxylic Acids, Esters & Polyesters_A level_OCR_Chemistry_Paper 1
Carbonyl Compounds,
Carboxylic Acids, Esters & Pol
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Question Paper 1
Level A Level
Exam Board OCR
Sub-Topic
Time Allowed: 86 minutes
Score: /71
Percentage: /100
Grade Boundaries:
A* A B C D E U
>85% 77.5% 70% 62.5% 57.5% 45% <45%
1 A student analysed a mixture of compounds found in red wine using gas chromatography followed
by mass spectrometry (GC-MS).
Two of the compounds found to be present in the mixture are shown below.
CHO
OCH3
compound A compound B
(a) The column in the gas chromatogram is packed with solid beads coated with a liquid polymer.
How does gas chromatography (GC) separate the compounds in the mixture?
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(b) The mass spectrum (MS) of the first compound to emerge from the column is shown below.
100
80
60
40
20
0
25 50
75
m / z
100
125 150
(i) Identify the compound responsible for this spectrum.
Give a reason for your answer.
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(ii) What does your answer to (b)(i) suggest about the interaction of this compound with the phases present in the column?
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(c) In red wine, compound A slowly forms an ester.
The formation of the ester can also be done in the laboratory, as shown in the flowchart below. Separate portions of compound A are used in the formation of the ester.
(i) Complete the boxes in the flowchart below.
CHO COOH
compound A
CHO
NaBH4
reaction 1
compound A
[3]
(ii) Give the mechanism to show the formation of compound C in reaction 1. Use curly arrows and relevant dipoles.
(d) 1 mol of compound B reacts with 2 mol of bromine, Br2 by electrophilic substitution.
OCH3
compound B
Write a balanced equation for this reaction, showing clearly the structure of the organic compound.
[1]
[Total: 10]
2 The following three carbonyl compounds are structural isomers of C5H10O2.
compound C
compound D
compound E
(a) Describe chemical tests that you could carry out in test-tubes to distinguish between compounds C, D and E.
Include appropriate reagents and any relevant observations. Also include equations showing structures for the organic compounds involved.
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