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Date	May 2017	Marks available	2	Reference code	17M.2.hl.TZ2.9
Level	HL	Paper	2	Time zone	TZ2
Command term	Calculate	Question number	9	Adapted from	N/A

Question

The Bombardier beetle sprays a mixture of hydroquinone and hydrogen peroxide to fight off predators. The reaction equation to produce the spray can be written as:

C₆H₄(OH)₂(aq) + H₂O₂(aq)	→	C₆H₄O₂(aq) + 2H₂O(l)
hydroquinone		quinone

Hydrogenation of propene produces propane. Calculate the standard entropy change, ΔS^θ, for the hydrogenation of propene.

[2]

b.i.

The standard enthalpy change, ΔH ^θ, for the hydrogenation of propene is –124.4 kJ mol^–1. Predict the temperature above which the hydrogenation reaction is not spontaneous.

[2]

b.ii.

Markscheme

«ΔS^θ =» 270 «J K^–1 mol^–1» – 267 «J K^–1 mol^–1» – 131 «J K^–1 mol^–1»

«ΔS^θ =» –128 «J K^–1 mol^–1»

Award [2] for correct final answer.

[2 marks]

b.i.

«non spontaneous if» ΔG ^θ = ΔH ^θ – TΔS ^θ > 0
OR
ΔH ^θ > TΔS ^θ

«T above» $\frac{{ - 124.4{\text{ }}\ll {\text{kJ}}\,{\text{mo}}{{\text{l}}^{ - {\text{1}}}}\gg }}{{ - 0.128{\text{ }}\ll {\text{kJ}}\,{{\text{K}}^{ - 1}}\,{\text{mo}}{{\text{l}}^{ - {\text{1}}}}\gg }} =$ » 972 «K»

Award [2] for correct final answer.

Accept 699 °C.

Do not award M2 for any negative T value.

[2 marks]

b.ii.

Examiners report

[N/A]

b.i.

[N/A]

b.ii.

Syllabus sections

Core » Topic 10: Organic chemistry » 10.1 Fundamentals of organic chemistry

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17M.2.hl.TZ2.6b:
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17M.3.sl.TZ1.10b.ii:
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18N.2.hl.TZ0.2d:
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Deduce the structural formula of the compound.
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18N.2.sl.TZ0.2a:
Draw the structural formula of propan-2-ol.
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Draw two structural isomers of methyloxirane.
17M.1.sl.TZ1.26: What is the name of the compound with this molecular structure applying IUPAC rules? A. ...
16N.1.sl.TZ0.24:
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A. I and II only

B. I and III only

C. II and III only

D. I, II and III
19N.3.sl.TZ0.10c: Explain why maltose, C12H22O11, is soluble in water.
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19N.2.sl.TZ0.3d(ii):
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19M.1.hl.TZ1.32: What is the IUPAC name of the following molecule? A. 2-bromo-3-ethylbutane B....
19M.1.hl.TZ2.34: What is the name of this compound using IUPAC rules? A. 2,3-diethylbutane B....
17M.1.hl.TZ2.37:
In which order should the reagents be used to convert benzene into phenylamine (aniline)?
19M.2.hl.TZ1.2c:
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19M.2.sl.TZ1.1b:
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19M.3.sl.TZ1.5a:
State the name of the functional group which allows the molecule to be responsive to applied electric fields.
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16N.3.sl.TZ0.20a:
Compare and contrast the functional groups present in methadone and diamorphine (heroin), giving their names. Use section 37 of the data booklet.
19M.1.sl.TZ2.24:
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B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃
19M.1.hl.TZ2.32:
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A. CH₃CH₂CH₂CH₂CH₂CH₃

B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃
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17M.3.sl.TZ1.15b:
Deduce the formula of the biodiesel formed when the vegetable oil shown is reacted with the reagents in (a).
17M.2.hl.TZ2.7c.i:
State the reagents and the name of the mechanism for the nitration of benzene.
17M.1.sl.TZ2.27:
Which compound contains a secondary carbon atom?

A. CH₃CH(Cl)CH(CH₃)₂

B. (CH₃)₂CHCH₂Cl

C. (CH₃)₃CCl

D. CH₃CH₂Cl
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17M.1.sl.TZ1.27:
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C. C₃H₇N(CH₃)₂

D. C₆H₅NH₂
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Suggest the structural formula of this compound.
17M.2.hl.TZ1.7c:
State the reagents used to convert benzene to nitrobenzene and the formula of the electrophile formed.
19N.3.sl.TZ0.7a:
Draw the structure of the dipeptide Asp–Phe using section 33 of the data booklet.
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19N.2.hl.TZ0.3d(iii):
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19N.2.hl.TZ0.3a(ii): State the IUPAC name of the major product.
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19N.3.hl.TZ0.24a:
Infrared (IR) spectroscopy is used to identify functional groups in organic compounds.

Deduce the wavenumber, in cm⁻¹, of an absorption peak found in the IR spectrum of testosterone but not in that of cholesterol.
17M.3.hl.TZ2.3c.iii:
Subsequent steps proceed under differing conditions, forming the dendrimer polymer with the following repeating unit.

State the name of one functional group in this repeating unit.
19N.2.hl.TZ0.3d(ii):
Explain why the compound C₃H₈O, produced in (a)(iv), has a higher boiling point than compound C₃H₆O, produced in d(i).
17M.2.sl.TZ1.6b:
State the typical reactions that benzene and cyclohexene undergo with bromine.
17M.1.sl.TZ1.25:
What are the functional groups in the aspirin molecule?

$\begin{gathered} \begin{array}{*{20}{l}} {{\text{I.}}}&{{\text{Ether}}} \\ {{\text{II.}}}&{{\text{Carboxyl}}} \\ {{\text{III.}}}&{{\text{Ester}}} \end{array} \hfill \\ \hfill \\ \end{gathered}$

A. I and II only

B. I and III only

C. II and III only

D. I, II and III
17M.2.sl.TZ1.6a:
Discuss the physical evidence for the structure of benzene.
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17M.2.hl.TZ2.7b.i:
Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.
18N.1.sl.TZ0.25:
What is the order of increasing boiling point for the isomers of C₅H₁₂?

A. CH₃CH₂CH₂CH₂CH₃ < CH₃CH(CH₃)CH₂CH₃ < CH₃C(CH₃)₃

B. CH₃C(CH₃)₃ < CH₃CH(CH₃)CH₂CH₃ < CH₃CH₂CH₂CH₂CH₃

C. CH₃C(CH₃)₃ < CH₃CH₂CH₂CH₂CH₃ < CH₃CH(CH₃)CH₂CH₃

D. CH₃CH(CH₃)CH₂CH₃ < CH₃C(CH₃)₃ < CH₃CH₂CH₂CH₂CH₃
19M.2.sl.TZ2.1c(ii):
State the name of product B, applying IUPAC rules.
18M.2.hl.TZ1.3d:
One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.
17M.2.sl.TZ1.5a:
Ethane, C₂H₆, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.
20N.1.hl.TZ0.40:
Which compound with the molecular formula $C_{4} H_{8} O$ has this high resolution ${}_{1}H NMR$ ?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A. but-3-en-2-ol, ${CH}_{2} = CHCH (OH) {CH}_{3}$

B. butanal, ${CH}_{3} {CH}_{2} {CH}_{2} CHO$

C. butanone, ${CH}_{3} {COCH}_{2} {CH}_{3}$

D. but-3-en-1-ol, ${CH}_{2} = {CHCH}_{2} {CH}_{2} OH$
17M.2.sl.TZ2.6b:
Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.
17M.3.sl.TZ1.10b.i:
Describe the difference in their structures.
19N.1.sl.TZ0.25: Which compound is not in the same homologous series as the others? A. C5H12 B. C6H12 C. ...
21N.1.sl.TZ0.26: Which pair of compounds are structural isomers? A. Propane and propene B. Propanal and...
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18M.3.sl.TZ2.2a:
Describe two differences, other than the number of atoms, between the models of ethane and ethene constructed from the kit shown.
19N.3.sl.TZ0.15a: State the names of two functional groups present in all three molecules, using section 37 of...
19N.3.sl.TZ0.9b: State one impact on health of the increase in LDL cholesterol concentration in blood.
20N.2.hl.TZ0.2e:
Compound A and B are isomers. Draw two other structural isomers with the formula $C_{3} H_{6} O$ .
20N.1.sl.TZ0.24: Which functional groups are present in this molecule? A. carbonyl, ether, nitrile B. ...
18M.3.sl.TZ2.2b.i:
The above ball and stick model is a substituted pyridine molecule (made of carbon, hydrogen, nitrogen, bromine and chlorine atoms). All atoms are shown and represented according to their relative atomic size.

Label each ball in the diagram, excluding hydrogens, as a carbon, C, nitrogen, N, bromine, Br, or chlorine, Cl.
17M.2.hl.TZ2.2a.v:
Identify one organic functional group that can react with acidified K₂Cr₂O₇(aq).
17M.2.hl.TZ2.7a.ii:
Identify the functional group that shows stretching at 1710 cm^–1 in the infrared spectrum of this compound using section 26 of the data booklet and the ¹H NMR.
17M.2.hl.TZ1.6c.i:
One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.
20N.3.sl.TZ0.9b: State a class of organic compounds found in gasoline.
19N.3.hl.TZ0.24b:
Describe a technique for the detection of steroids in blood and urine.
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22M.2.sl.TZ1.3c(i):
State the name of Compound A, applying International Union of Pure and Applied Chemistry (IUPAC) rules.
17M.3.hl.TZ2.20a.iii:
Suggest two absorbances, other than the absorbances due to the ring structure and C–H bonds, that would be present in the infrared (IR) spectrum of aspirin.
17M.2.sl.TZ1.5c.i:
One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.
20N.2.sl.TZ0.1d(v):
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion. Draw the structural formula of ethoxyethane
19N.3.hl.TZ0.24c:
Explain how redox chemistry is used to measure the ethanol concentration in a breathalyser.
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18M.3.sl.TZ2.2b.iii:
Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.
20N.3.hl.TZ0.11b: State a class of organic compounds found in gasoline.
20N.3.hl.TZ0.11e(iii):
Suggest a wavenumber absorbed by methane gas.
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21M.1.sl.TZ2.28:
Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

I. mass
II. infrared
III. ¹H NMR

A. I and II only

B. I and III only

C. II and III only

D. I, II and III
18M.2.sl.TZ2.7a:
The Kekulé structure of benzene suggests it should readily undergo addition reactions.

Discuss two pieces of evidence, one physical and one chemical, which suggest this is not the structure of benzene.
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21M.2.sl.TZ1.5a(ii): State the molecular formula of the next member of the homologous series to which ethene belongs.
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21M.2.sl.TZ2.4c:
Write the equation and name the organic product when ethanol reacts with methanoic acid.
20N.2.sl.TZ0.2c:
Compound A and B are isomers. Draw two other structural isomers with the formula $C_{3} H_{6} O$ .
17M.2.sl.TZ2.6a:
Using relevant equations, show the initiation and the propagation steps for this reaction.
20N.2.hl.TZ0.1d(iv):
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion.
Draw the structural formula of ethoxyethane
20N.2.hl.TZ0.2d:
The IR spectrum of one of the compounds is shown:

COBLENTZ SOCIETY. Collection © 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.

Deduce, giving a reason, the compound producing this spectrum.
19M.2.hl.TZ1.1b:
Draw the structure of one other isomer of xylene which retains the benzene ring.
20N.2.hl.TZ0.4c: Discuss, referring to intermolecular forces present, the relative volatility of propanone and...
20N.2.sl.TZ0.2b:
The IR spectrum of one of the compounds is shown:

COBLENTZ SOCIETY. Collection © 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.

Deduce, giving a reason, the compound producing this spectrum.
20N.3.sl.TZ0.9f(iii):
Suggest a wavenumber absorbed by methane gas.
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22M.2.hl.TZ2.8d(iv):
Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).
22M.2.hl.TZ2.8e(ii):
Deduce the splitting pattern in the ¹H NMR spectrum for 1-bromopropane.
19M.2.hl.TZ2.1c(ii):
Determine the enthalpy change for the reaction, in kJ, to produce A using section 11 of the data booklet.
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22M.2.sl.TZ2.4d(i): Draw the full structural formula of but-2-ene.
22M.2.sl.TZ2.4d(iv):
Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).
17M.2.hl.TZ1.6c.ii:
The mass and ¹H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.
18M.2.sl.TZ1.3c:
One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.
17M.2.sl.TZ1.5c.ii:
The mass and ¹H $\,$ NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.
21M.1.sl.TZ1.24: Which series is in order of increasing boiling point? A. CH2CH2CH3OH CH3COCH3 ...
22M.1.sl.TZ2.26:
Which is a homologous series?

A. C₂H₄, C₃H₅, C₄H₆

B. C₂H₂, C₃H₄, C₄H₆

C. C₂H₂, C₂H₄, C₂H₆

D. C₂H₂, C₄H₄, C₆H₆
21N.1.sl.TZ0.25: What is the name of this substance using IUPAC rules? A. 2-ethyl-1-methylbutan-1-ol B. ...

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