Paper 1 Section B Data-based question (6) with worked
answers
Compound X is a crystalline solid that occurs naturally in some fruits.
Analysis of pure Compound X shows that it contains 68.84% carbon, 4.96% hydrogen and 26.20% oxygen
by mass.
The mass spectrum of Compound X shows a molecular ion peak with m/z = 122.
The low resolution 1H NMR spectrum of Compound X shows two signals with an integration trace ratio
of 5:1.
The infrared spectrum of Compound X shows a broad strong peak between 2500 and 3000 cm-1 and a
sharp peak at 1700 cm-1.
(a) (i) Show that the molecular formula of Compound X is C7H6O2. [2]
From the elemental analysis
The empirical formula is C7H6O2 [1]
The molecular ion peak gives M as 122 g mol−1 so the molecular formula is C7H6O2 [1]
(Underlying chemistry concepts can be found in S1.4 Counting particles by mass- the mole.)
(ii) State the information that can be deduced about the structure of Compound X from its 1H NMR
spectrum. [2]
The hydrogen atoms in the molecule exist in two different chemical environments. [1]
Five H atoms are in the same environment and one is in a different environment. [1]
(Underlying chemistry concepts can be found in S3.2 (AHL) Mass spectrometry, IR & 1H NMR
spectroscopy.)
© Dr. Geoffrey Neuss, InThinking
https://www.thinkib.net/chemistry 1
(iii) Deduce the molecular structure of Compound X. [1]
C6H5COOH. [1]
(C6H5COOH fits the mass spectral and 1H NMR data. The IR data confirms this structure as the broad
strong peak between 2500 and 3000 cm-1 is due to −OH and the sharp peak at 1700 cm-1 is due to C=O.
Underlying chemistry concepts can be found in S3.2 (AHL) Mass spectrometry, IR & 1H NMR
spectroscopy.)
(b) The value for the acid dissociation constant of Compound X is 6.31 x 10-5. Using HX to represent
Compound X, state the equation for the reaction of Compound X with water. [1]
HX(aq) + H2O(l) ⇌ X−(aq) + H3O+(aq) or HX(aq) ⇌ X−(aq) + H+(aq) [1]
(Note that to gain the mark the equation must have reversible arrows as the value for the equilibrium
constant shows that it is a weak acid.)
(Underlying chemistry concepts can be found in R3.1 Strong & weak acids & bases.)
(c) The following table shows the solubility of Compound X in water at different temperatures:
Suggest how an impure sample of Compound X could be purified in a school laboratory. [1]
Recrystallise Compound X from distilled water. [1]
(Dissolve in boiling water, filter to remove any insoluble impurities, leave to cool then filter off the
crystals and wash with a little cold distilled water before drying.)
(Underlying chemistry concepts can be found in S1.1 Introduction to the particulate nature of matter.)
© Dr. Geoffrey Neuss, InThinking
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(d) Compound X reacts with propan-1-ol when warmed in the presence of a sulfuric acid catalyst. The
inorganic product obtained in this reaction is water.
(i) State the name of the type of reaction that is taking place. [1]
Condensation or esterification [1]
(Underlying chemistry concepts can be found in S2.4 (AHL) From models to materials.)
(ii) Deduce the molecular formula of the organic product. [1]
C7H6O2 + C3H8O → H2O + C10H12O2 so the molecular formula is C10H12O2 [1]
(Underlying chemistry concepts can be found in S2.4 (AHL) From models to materials.)
© Dr. Geoffrey Neuss, InThinking
https://www.thinkib.net/chemistry 3
