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Date	May 2017	Marks available	2	Reference code	17M.2.sl.TZ1.5
Level	SL	Paper	2	Time zone	TZ1
Command term	Determine	Question number	5	Adapted from	N/A

Question

This question is about carbon and chlorine compounds.

Ethane, C₂H₆, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.

[1]

a.

Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.

[3]

b.

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.

[2]

c.i.

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.

[3]

c.ii.

Chloroethene, C₂H₃Cl, can undergo polymerization. Draw a section of the polymer with three repeating units.

[1]

d.

Markscheme

substitution AND «free-»radical
OR
substitution AND chain

Award [1] for “«free-»radical substitution” or “S_R” written anywhere in the answer.

[1 mark]

a.

Two propagation steps:
C₂H₆ + •Cl → C₂H₅• + HCl

C₂H₅• + Cl₂ → C₂H₅Cl + •Cl

One termination step:
C₂H₅• + C₂H₅• → C₄H₁₀
OR
C₂H₅• + •Cl → C₂H₅Cl
OR
•Cl + •Cl → Cl₂

Accept radical without • if consistent throughout.

Allow ECF from incorrect radicals produced in propagation step for M3.

[3 marks]

b.

${\text{C}} = \frac{{24.27}}{{12.01}}$ = 2.021 AND ${\text{H}} = \frac{{4.08}}{{1.01}}$ = 4.04 AND ${\text{Cl}} = \frac{{71.65}}{{35.45}} = 2.021$

«hence» CH₂Cl

Accept $\frac{{24.27}}{{12.01}}$ : $\frac{{4.08}}{{1.01}}$ : $\frac{{71.65}}{{35.45}}.$

Do not accept C₂H₄Cl₂.

Award [2] for correct final answer.

[2 marks]

c.i.

molecular ion peak(s) «about» m/z 100 AND «so» C₂H₄Cl₂ «isotopes of Cl»

two signals «in ¹H $\,$ NMR spectrum» AND «so» CH₃CHCl₂
OR
«signals in» 3:1 ratio «in ¹H $\,$ NMR spectrum» AND «so» CH₃CHCl₂
OR
one doublet and one quartet «in 1H $\,$ NMR spectrum» AND «so» CH₃CHCl₂

1,1-dichloroethane

Accept “peaks” for “signals”.

Allow ECF for a correct name for M3 if an incorrect chlorohydrocarbon is identified

[3 marks]

c.ii.

Continuation bonds must be shown.

Ignore square brackets and “n”.

Accept .

Accept other versions of the polymer, such as head to head and head to tail.

Accept condensed structure provided all C to C bonds are shown (as single).

[1 mark]

d.

Examiners report

[N/A]

a.

[N/A]

b.

[N/A]

c.i.

[N/A]

c.ii.

[N/A]

d.

Syllabus sections

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

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19M.1.sl.TZ2.24:
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19M.1.hl.TZ2.32:
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17M.1.sl.TZ2.27:
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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:
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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?

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

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C. II and III only

D. I, II and III
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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:
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B. CH₃C(CH₃)₃ < CH₃CH(CH₃)CH₂CH₃ < CH₃CH₂CH₂CH₂CH₃

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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, ${CH}_{3} {COCH}_{2} {CH}_{3}$

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17M.3.sl.TZ1.10b.i:
Describe the difference in their structures.
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18M.3.sl.TZ2.2a:
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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.
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19N.3.hl.TZ0.24b:
Describe a technique for the detection of steroids in blood and urine.
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State the name of Compound A, applying International Union of Pure and Applied Chemistry (IUPAC) rules.
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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.
20N.2.sl.TZ0.1d(v):
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion. Draw the structural formula of ethoxyethane
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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.
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Suggest a wavenumber absorbed by methane gas.
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Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

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A. I and II only

B. I and III only

C. II and III only

D. I, II and III
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The Kekulé structure of benzene suggests it should readily undergo addition reactions.

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Write the equation and name the organic product when ethanol reacts with methanoic acid.
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Using relevant equations, show the initiation and the propagation steps for this reaction.
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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.
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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.
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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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