2208-6108
13 pages
M08/4/CHEMI/HP2/ENG/TZ1/XX
Thursday 8 May 2008 (afternoon)
CHEMISTRY
HIGHER lEvEl
PaPER 2
INSTRUCTIONS TO CANDIDATES
•
Write your session number in the boxes above.
•
Do not open this examination paper until instructed to do so.
•
Section A: answer all of Section A in the spaces provided.
•
Section B: answer two questions from Section B. Write your answers on answer sheets. Write
your session number on each answer sheet, and attach them to this examination
paper and your cover sheet using the tag provided.
•
At the end of the examination, indicate the numbers of the questions answered in the candidate
box on your cover sheet and indicate the number of sheets used in the appropriate box on your
cover sheet.
2 hours 15 minutes
Candidate session number
0
0
© International Baccalaureate Organization 2008
22086108
0113
2208-6108
–2–
M08/4/CHEMI/HP2/ENG/TZ1/XX
Section a
Answer all the questions in the spaces provided.
1.
Thevalueofxin
Fe(NH ) (SO )
4 2
4 2
.
xH O
2
canbefoundbydeterminingtheamount,inmoles,of
sulfateinthecompound.
A0.982gsamplewasdissolvedinwaterandexcess
BaCl (aq)
2
wasadded.
Theprecipitateof
BaSO
4
wasseparatedanddriedandfoundtoweigh1.17g.
(a) Calculatetheamount,inmolesof
BaSO
4
inthe1.17gprecipitate.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(b) Calculate the amount, in moles, of sulfate in the 0.982 g sample of
Fe(NH ) (SO )
4 2
4 2
.
xH O
2
.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[1]
(c) Calculatetheamount,inmoles,ofironinthe0.982 gsampleof
Fe(NH ) (SO )
4 2
4 2
.
xH O
2
.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[1]
(d) Determine the mass of the following present in the 0.982 g sample of
Fe(NH ) (SO )
4 2
4 2
.
xH O
2
.
[3]
(i) Iron
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Ammonium
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Sulfate
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(This question continues on the following page)
0213
2208-6108
––
turn over
M08/4/CHEMI/HP2/ENG/TZ1/XX
(Question 1 continued)
(e) Useyouranswerfrompart(d)todeterminetheamount,inmoles,ofwaterpresentinthe
0.982gsampleof
Fe(NH ) (SO )
4 2
4 2
.
xH O
2
.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(f) Determinetheamount,inmoles,of
Fe(NH ) (SO )
4 2
4 2
andhencethevalueofx.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
0313
2208-6108
–4–
M08/4/CHEMI/HP2/ENG/TZ1/XX
2.
(a) The mass spectrometer is used to investigate the isotopic composition of elements.
Thalliumhastwoisotopes
81
203
Tland
81
205
Tl.
(i) State the symbols of the two singly charged ions that would form in the
massspectrometer.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[1]
(ii) StatewhichionwillfollowthepathmarkedXonthediagram.
[1]
detector
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Somedoublychargedionsforminthemassspectrometer.Suggestwithareason
whether they would be deflected less than or more than the ions at XandY.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(b) Naturallyoccurringboronconsistsofthetwoisotopes,
10
B
and
11
B
.Therelativeatomic
massofboronis10.81.Determinethepercentageabundanceoftheseisotopes.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
X
Y
magnetic field
0413
2208-6108
––
turn over
M08/4/CHEMI/HP2/ENG/TZ1/XX
3.
Lacticacid,
CH CH(OH)COOH
,isaweakmonoproticacid(
K
a
moldm
=
×
−
−
1 40 10
4
.
.
).
(a) Writeanequationforthereactionoflacticacidwithwater.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(b) Statetheionizationconstantexpression,
K
a
,forlacticacid.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[1]
(c) Calculatethe
[ ]
H
+
ofa0.20mol
dm
−
solutionoflacticacid.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(d) Calculatethe
[ ]
H
+
ofabuffersolutionof1.00
dm
volume,containing0.20mol
dm
−
of
lacticacidand0.12mol
dm
−
ofsodiumlactate.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
(e) Explain why the two values of
[ ]
H
+
in (c) and (d) are different using Le Chatelier’s
principle.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
0513
2208-6108
–6–
M08/4/CHEMI/HP2/ENG/TZ1/XX
4.
(a) Explainwhatismeantbythetermisomers?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[1]
(b) Drawtwostructuralisomersforeachofthefollowingwithdifferent functional groups.
Ineachcase,describeachemicaltestandtheresultsobtained,whichwoulddistinguish
betweenthetwostructuralisomers.
(i)
C H O
6
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[4]
(ii)
C H O
6
2
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[4]
0613
2208-6108
–7–
turn over
M08/4/CHEMI/HP2/ENG/TZ1/XX
5.
Two1 00
3
. dm containersaandBeachcontain2.00gofthegasindicatedat
2 0
. °C
.
O
2
a
B
(a) Calculatethepressureincontainer
B.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[3]
(b) Deducewithout calculationwhetherthepressureinaishigherorlowerthancontainer
Bandexplainyouranswer.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
[2]
H
2
0713
2208-6108
–8–
M08/4/CHEMI/HP2/ENG/TZ1/XX
Section B
Answer two questions. Write your answers on the answer sheets provided. Write your session number
on each answer sheet, and attach them to this examination paper and your cover sheet using the tag
provided.
6.
(a) Thedecompositionofsolidbariumcarbonateisgivenbythefollowingequation:
BaCO (s)
BaO
(s) CO (g)
3
�
+
2
Compound
BaCO (s)
CO (g)
2
BaO(s)
∆
H
f
kJmol
Ö
/
−1
–1219
–94
–8
S
Ö
/ JK mol
−1
−1
+112
+214
+70
(i) Calculatethevalueof
∆
G
Ö
inkJmol
−1
at
2°C
.
[6]
(ii) Statewithareasonwhetherthereactionisspontaneousat
2°C
.
[1]
(iii) Determine the minimum temperature above which this reaction is spontaneous.
Explainyouranswer.
[4]
(b) DrawtheLewisstructuresofthefollowingmolecules.UsetheVSEPRtheorytopredict
theshapeofeachmolecule.
(i)
XeF
4
and
XeO
4
[4]
(ii)
PF
and
IF
[4]
(c) Transitionelementsformcomplexessuchas
[Fe(Cl) ]
4
−
and
[Fe(CN) ]
6
4−
.
(i) Identifythefeatureofboth
Cl
−
and
CN
−
thatenablesthemtoformthesecomplexes
andnamethetypeofbondformed.
[2]
(ii) Deducetheoxidationstateofironineachofthecomplexions.
[2]
(iii) State
two characteristic properties of transition metals other than complex
formationandvariableoxidationstate.
[2]
0813
2208-6108
–9–
turn over
M08/4/CHEMI/HP2/ENG/TZ1/XX
7.
(a) Theoxidationofnitrogenmonoxidetakesplaceasfollows:
2NO (g) O (g)
2NO (g)
2
2
+
→
Thefollowingexperimentaldatawasobtainedataconstanttemperature.
Experiment Initial[NO]/mol
dm
−
Initial
[ ]
O
2
/mol
dm
−
Initialrate/mol
dm s
− −
1
1
0 10
2
. ×
−
1 7 10
2
. ×
−
7 10
. ×
−
2
0 10
2
. ×
−
0 10
2
. ×
−
7 0 10
. ×
−
7 00 10
2
. ×
−
7 00 10
2
. ×
−
6 00 10
2
. ×
−
(i) Deducetheorderofreactionwithrespectto
O
2
andwithrespecttoNO.
[2]
(ii) Statetherateexpressionforthereaction.
[1]
(iii) Calculatethevalueoftherateconstantandstatetheunits.
[2]
(iv) Calculate the expected rate of reaction if the reactants from experiment 2 were
placedinacontaineroftwicetheoriginalvolume.Explainyouranswer.
[2]
(v) Suggestapossibletwostepmechanismthatisconsistentwiththerateexpression.
Identifytherate-determiningstep.
[3]
(b) Thereactionin(a)isfasterat2Kthanat298K.Explaintheincreaseinrateinterms
ofcollisiontheoryandMaxwell-Boltzmannenergydistributioncurves.
[5]
(This question continues on the following page)
0913
2208-6108
–10–
M08/4/CHEMI/HP2/ENG/TZ1/XX
(Question 7 continued)
(c) Thefollowingequilibriumisinvolvedintheindustrialproductionofnitricacidfrom
ammonia.
4
4
910
1
NH (g) O (g)
NO(g) 6H O(g)
kJmol
2
2
+
+
= −
−
∆
H
Ö
Describe the effect, if any, of each of the following changes on the equilibrium
concentrationofnitrogenmonoxideinaparticularequilibriummixture,giveareasonin
eachcase.
(i) Increasingthepressure,atconstanttemperature
[2]
(ii) Increasingthetemperature,atconstantpressure
[2]
(iii) Additionofaheterogeneouscatalyst,atconstantpressureandtemperature
[2]
(d) Deducetheequilibriumconstantexpression,
K
c
,includingunitsfortheforwardreaction
inpart(c).
[2]
(e) Identifywhichofthechangesinpart(c)willaffectthevalueof
K
c
andpredictwhether
thevalueof
K
c
willincreaseordecrease.
[2]
1013
2208-6108
–11–
turn over
M08/4/CHEMI/HP2/ENG/TZ1/XX
8.
(a) Electrolysisofanaqueoussolutionofcopper(II)sulfate,
CuSO
4
,canbecarriedoutusing
platinumelectrodes.
(i) Stateanequationforthehalf-reactionoccurringatthepositiveelectrode(anode)
and
oneobservationthatcouldbemadeasaresult.
[2]
(ii) Stateanequationforthehalf-reactionoccurringatthenegativeelectrode(cathode)
and
oneobservationthatcouldbemadeasaresult.
[2]
(iii) Describe
two changes or observations in the electrolyte as result of these
halfreactions.
[2]
(iv) Determinetherelativeamount,inmoles,ofproductsformedateachelectrode.
[1]
(v) Identifyanothercompoundwhichwillformthesameproductsatthepositiveand
negativeelectrodes.
[1]
(vi) Thesameprocessiscarriedoutusingcopperelectrodesinsteadoftheplatinum
electrodes. Describe the changes or observations that take place at both the
electrodesandintheelectrolyte.
[3]
(b) Identify
twofactorsthataffectthequantityofcopperproducedduringtheelectrolysisof
anaqueouscopper(II)sulfatesolution.
[1]
(c) Considerthefollowinghalfcellreactionsandtheirstandardelectrodepotentials.
Ni (aq)
e
Ni(s)
V
2+
−
+
= −
2
0 2
E
Ö
.
MnO (aq) 8H (aq) e
Mn (aq) 4H O (l)
V
2
2
4
1 1
−
+
−
+
+
+
+
= +
E
Ö
.
(i) State the conditions needed for the electrode potentials to be described as
standard.
[1]
(ii) Deduceabalancedequationfortheoverallreactionwhichwilloccurspontaneously
whenthetwohalfcellsareconnected.
[2]
(iii) Identify the reducing agent in the above reaction and determine the change in
oxidationnumberforthe
oxidizing agent.
[2]
(iv) Determinethecellpotentialwhenthetwohalfcellsareconnected.
[1]
(v) Drawandlabeladiagramofthevoltaiccellfrompart(c).Indicatetheanode,
cathode, the direction of the electron movement and ion flow.
[5]
(d) Outline
twodifferencesbetweenanelectrolyticcellandavoltaiccell.
[2]
1113
2208-6108
–12–
M08/4/CHEMI/HP2/ENG/TZ1/XX
9.
(a) Ahydrocarboncontains8.6%bymassofcarbonandhasamolarmassof6.1
gmol
−1
.
(i) Determinetheempiricalandmolecularformulasofthehydrocarbon.
[3]
(ii) Drawthestructureoftheunsaturatedbranchedisomerandpredicttheratioofthe
peakareasinits
1
HNMR
spectrum.
[2]
(iii) Thesecondstructuralisomerofthehydrocarbonisunsaturatedandsymmetrical.
Drawitsstructureandstateitsname.
[2]
(iv) Draw the structure of the third structural isomer of this hydrocarbon which is
unsaturated, unbranched and unsymmetrical. This isomer is formed when an
alcoholisheatedwithconcentratedsulfuricacid.Identifythetypeofreaction
occurringanddeducethestructureofanalcoholthatformsthisisomer.
[3]
(b) The hydrolysis of 2-bromo-2-methylbutane by 0.10 mol
dm
−
potassium hydroxide
solutiontoform2-methylbutan-2-olisanexampleofan
S 1
N
reaction.
(i) Explainhowthis
S 1
N
reactionoccurs,usingcurlyarrowstorepresentthemovement
ofelectronpairs,andshowingthestructureoftheorganicintermediate.
[4]
(ii) Identifytheratedeterminingstepandstateareasonforyourchoice.
[1]
(c) State and explain whether the rate of each of the following reactions is greater than,
lessthanorequaltotherateofthereactioninpart(b).
(i) 2-chloro-2-methylbutane is reacted with 0.10 mol
dm
−
KOH (aq) at the
sametemperature.
[1]
(ii) 2-bromo-2-methylbutane is reacted with 0.20 mol
dm
−
KOH (aq) at the same
temperature.
[1]
(This question continues on the following page)
1213
2208-6108
–1–
M08/4/CHEMI/HP2/ENG/TZ1/XX
(Question 9 continued)
(d) (i) Discuss the structure of benzene including the hybridization and bond
anglespresent.
[4]
(ii) State, with a reason, the number of main peaks in the
1
HNMR
spectrum of
benzene.
[2]
(e) (i) Cyclohexenereactswithhydrogentoformcyclohexane.
Calculate the enthalpy change of hydrogenation of benzene to cyclohexane,
assumingithasthecyclohexatriene
structure.
[1]
(ii) The experimental value for the hydrogenation of benzene to cyclohexane is
–207
kJmol
−1
.Explainwhythisvaluediffersfromthevaluecalculatedin(e)(i).
[1]
→
H
2
+
∆
H
Ö
=
−
–120
1
kJ mol
1313