Aqa Chem3
Aqa Chem3
Aqa Chem3
abc
General Certificate of Education
Chemistry 5421
CHM3/W
Mark Scheme
2008 examination - June series
Mark schemes are prepared by the Principal Examiner and considered, together with the relevant questions, by a panel of subject teachers. This mark scheme includes any amendments made at the standardisation meeting attended by all examiners and is the scheme which was used by them in this examination. The standardisation meeting ensures that the mark scheme covers the candidates responses to questions and that every examiner understands and applies it in the same correct way. As preparation for the standardisation meeting each examiner analyses a number of candidates scripts: alternative answers not already covered by the mark scheme are discussed at the meeting and legislated for. If, after this meeting, examiners encounter unusual answers which have not been discussed at the meeting they are required to refer these to the Principal Examiner. It must be stressed that a mark scheme is a working document, in many cases further developed and expanded on the basis of candidates reactions to a particular paper. Assumptions about future mark schemes on the basis of one years document should be avoided; whilst the guiding principles of assessment remain constant, details will change, depending on the content of a particular examination paper.
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CHM3/W
Question 1 (a) (i) A compound OR molecule containing OR consisting of hydrogen and carbon only C9H20 + 9O2 M1 High temperature OR spark OR 2500oC T 4000oC M2 Or multiple + 2 Ignore very when referring to high temperature 1
(a)
(ii)
9CO
+ 10H2O
Or multiple
(a)
(iii)
N2
O2
NO
(b)
(i)
(b)
(ii)
25 NO
8 CO2
12 N2
9 H2O
(c)
(d)
1O2
SO2 + H2O
Or multiple
Question 2 (a) M1 propanone M2 CH3CH2CHO OR correct aldehyde with functional group drawn out. (b) (c) Penalise CH=O for the aldehyde group 2 Credit propan-2-one as the only other acceptable response.
1 1
1 1 1
Elements in any order Either word ONLY Carboxylic acid group must show both the double and the single bonds to oxygen.
No mark for choice of reagent, but do not award the mark if no reagent given.
Structure for
CH2BrCHBrCH2OH
and CH2BrCHBrCOOH
Question 3 (a) (a) (i) (ii) (free-) radical substitution 1 Both words needed Ignore reference to uv/sunlight/heat.
Initiation:
Cl2
2Cl
(b)
(i)
dichlorodifluoromethane OR 1,1-dichloro-1,1-difluoromethane
(b)
(ii)
(b)
(iii)
propagation (step)
Polar C-Br (bond) OR + C OR partially positive carbon atom on C-Br (bond) (-) Br
(a)
(ii)
M1 must show an arrow from the lone pair of electrons on the nitrogen atom of the ammonia to the C atom of the C-Br bond. M2 must show the movement of a pair of electrons from the C-Br bond to the Br atom. Mark M2 independently. M3 is for the structure of the alkylammonium ion and could be obtained from CH3CH2NH3+ M4 is for an arrow from the N-H bond to the N atom. The second mole of ammonia is not essential for full credit, therefore ignore this part even if other species are used.
Award full marks for an SN1 mechanism in which M1 is the attack of the ammonia on the intermediate carbocation.
Penalise once only for a line and two dots to show a bond.
(b)
Name: propan(e)nitrile
OR propan(e)-1-nitrile 1
(c)
(i)
Electron pair donor OR Forms a coordinate / covalent bond by the reaction of OR attack by an electron pair / pair of electrons.
Insist on both electron pair and an action by the electron pair. Accept lone pair
(c)
(ii)
The minus sign can be anywhere on the OH The electron pair (if drawn) MUST be on the oxygen atom
Question 5 (a)
3-methylbut-1-ene
Elimination
ONLY
(b)
Penalise M3 for formal charge on C or incorrect partial charges or extra arrow from Br to e.g. K+
M1 must show an arrow from the lone pair on oxygen of a negatively charged hydroxide ion to the correct H atom. M2 must show an arrow from the correct C-H bond to the correct C-C bond and should only be awarded if an attempt has been made at M1 M3 is independent.
Award full marks for an E1 mechanism in which M2 is on the correct carbocation.
Penalise once only for a line and two dots to show a bond.
Max 2 marks for the mechanism for wrong reactant or sticks Ignore incorrect organic product
(c)
(i)
Structure OR name
2-bromo-3-methylbutane
OR
(CH3)2CHCHBrCH3 Apply list principle if both structure and name given
(c)
(ii)
Both words
(d)
CH3CH2CH=CHCH3
Credit M1 with a structure which is either linear or cis or trans (or both)
M2 Type:
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Question 6 (a)
M1 (Separation based on boiling point) Separation depends on boiling point. (Ignore reference to melting point or density)
Maximum 2 marks if candidate refers to bond breaking or cracking or using a Blast furnace or adding oxygen/air.
M2 (Link between boiling point and size/forces) Boiling point depends on Mr OR molecular size OR chain length OR intermolecular / Van der Waals forces OR candidate links boiling point with heavier/lighter fractions. M3 (Specified temperature gradient) Specified temperature gradient OR difference stated on column/tower OR explained e.g. hotter at bottom. (If numbers used, accept up to 400oC at the base and down to 25oC at top) M4 (Position of molecules/fractions on column) Lower Mr OR lower boiling point OR shorter chains OR smaller molecules OR more volatile/gaseous molecules OR lighter fractions (condense) at top (OR converse at bottom)
(b) M1 Thermal cracking M2 Any T (or range) in the range 400oC to 900oC OR High temperature. M3 (Free- OR alkyl-) radical Mark M1, M2 and M3 independently 3
QoL for M2
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(c)
M1 Yeast or suitable enzyme (zymase) M2 Fermentation M3 C6H12O6 2CH3CH2OH + 2CO2 (or 2C2H5OH) If O2 is in the equation, penalise the equation (M3) but NOT M1 Mark M1, M2 and M3 independently
Penalise C2H6O
(d)
There are two processes and therefore assume that the order of answers is the order of marking unless annotated by the candidate
M2 c(oncentrated) H3PO4 OR c(oncentrated) H2SO4 OR Al2O3 OR alumina OR porous pot OR pumice M3 (acid-catalysed) dehydration OR elimination
Mark M1, M2 and M3 independently (e)
M1
OR
CH2CH2
For M1, insist on bonds either side of CH2 groups For M1 ignore n and brackets Insist on C-O bonds in M2 structure.
M2
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. .
Br
H3C
. . Br
_ Curlyarrowsshouldoriginateeitherfromalonepairofelectronsorfroma .. _ : OH bond.Eachofthefollowingrepresentationsshouldnotgaincredit. OH
1. Theabsenceofaradicaldotinafreeradicalsubstitutionshouldbe penalisedonceonlywithinaclip. 2. Theuseofdoubleheadedarrowsortheincorrectuseofhalfheaded arrowsinfreeradicalmechanismsshouldbepenalisedonceonly withinaclip. B.Structures 1. Bondsshouldbedrawncorrectlybetweentherelevantatoms. Forexample,ifcandidatesshowthealcoholfunctionalgroupasCHO, theyshouldbepenalisedoneveryoccasion. 2. SomelatitudeshouldbegiventotherepresentationofCCbondsin structures,giventhatCH3isconsideredtobeinterchangeablewith H3Ceventhoughthelatterwouldbepreferred. 3. PoorpresentationofverticalCCbondsshouldnotgaincredit.
4. Theuseofsticksinstructuresshouldnotgaincredit.Theoccasionsthatthis applieswillbeindicatedinthemarkscheme. 5. Someexamplesofformulaeforspecificcompoundswhichshouldnotgain creditaregivenhere CH3COHforethanal CH2OCH2orCH2CH2Oforepoxyethane CH3CH2HOforethanol OHCH2CH3 C2H6O(exceptwhenspecificallyindicatedinthemarkscheme) CH2CH2forethene CH2.CH2 CH2:CH2 (N.B.Exceptionsmaybemadeinthecontextofbalancingequations)
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C.Names
Asageneralprinciple,nonIUPACnamesorincorrectspellingorincompletenames shouldnotgaincredit.Someillustrationsaregivenhere. but2ol 2hydroxybutaneallshouldbebutan2ol butane2ol 2butanol 2methpropan2olshouldbe2methylpropan2ol 2methylbutan3olshouldbe3methylbutan2ol 3methylpentanallshouldbe3methylpentane 3mythylpentane 3methypentane propanitrileshouldbepropanenitrile aminethaneshouldbeethylamine(although aminoethanecangaincredit)
2methyl3bromobutaneallshouldbe2bromo3methylbutane
3bromo2methylbutane 3methyl2bromobutane 2methylbut3eneshouldbe3methylbut1ene difluorodichloromethaneshouldbedichlorodifluoromethane
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