2 CH 2 O (-) Na (+) This equation scores (2) marks. CH 2 OHCH 2 O (-) Na (+)

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1 (a) Na + O (-) Na (+) O (-) Na (+) O (-) Na (+) + This equation scores () marks Accept multiples and ( ) and ( O (-) Na (+) ) Organic product (harges not needed) Na (+) O (-) Na (+) O (-) Reject bond from to Na Balancing and the rest for one mark: Na + + ½ Accept multiples O (-) Na (+) (b) Remove thermometer / still-head / leave the Sealed apparatus, top of condenser open e.g. wi thermometer in the Place condenser directly on top of flask/in top vertical position correct diagram for marks IGNE comments on use of electric heaters, changing concentration of reagents

2 (c) Displayed formula O O O the bond to be displayed displayed formula as working out any orientation Just Structural formula Bond from carbon clearly to the of the IGNE bonds of different lengths or incorrect bond angles (d) Both have / hydroxyl groups ydroxide ions Both would produce steamy / misty /white and fumes /gas (of l) White smoke Just both produce l Both give the same products (e)(i) (Strong) Peak at (cm - ) peak at (cm - ) peak at Peak(s) (either or both) at (cm - ) (cm - ) these if merged (e)(ii) (Unreacted) ethanol 5 /displayed /skeletal IGNE references to O- bonding Molecular formula Just O- in alcohol Ethane-,-diol

3 (e)(iii) (f)(i) O + O + 3 OO + O + the + sign wherever it is seen Also allow correct displayed, semi-displayed or structural formulae O - or any other formula with charge 3 O + 3 O + 3 O + 3 One mark for curly arrow from hydroxide ion; (This arrow can be drawn from anywhere on the hydroxide ion) arbon with - One mark for curly arrow from -Br bond orrect products; Bond to of If SN is shown, then intermediate with positive charge must be shown after loss of Br, followed by attack by hydroxide. This mechanism can score all 3 marks (f)(ii) Mechanism: Nucleophilic Type: Substitution either way round Just S N scores nucleophile and phonetic spelling IGNE eterolytic fission Elimination SN with elimination or other type of reaction omolytic fission

4 (g) Ag + (aq) + Br - (aq) AgBr(s) Spectator ions included Species State symbols one mark for chemical equation with state symbols rather than ionic equation, e.g. AgNO 3 (aq) + NaBr(aq) AgBr(s) + NaN 3 (aq) (h Both silver chloride and silver bromide dissolve /give colourless solution in conc. ammonia If the solid doesn t dissolve in dilute ammonia then it is silver bromide Add conc. sulfuric acid to the (solid) silver bromide and get red-orange bromine gas Alternative tests which don t work eg displacement of bromine, use of organic solvent, leave in sunlight to see if bromine forms, add conc. sulfuric acid to halide solution.

5 (a)(i) X = -chloro--methylpropane X =,-chloromethylpropane X = -methyl--chloropropane X =,-methylchloropropane X = -chloromethylpropane -methylchloropropane Z = -methylpropan--ol methylpropan--ol propane for propan ydroxy for -ol IGNE omission of (or extra) commas and hyphens IGNE spaces (a)(ii) l Any other type of structure any angles (a)(iii) (b)(i) Tertiary recognisable abbreviations: 3 y /3º Nucleophilic Substitution S N scores / S N

6 (b)(ii) Movement ( Transfer/donation)/ start and finish positions of an electron pair two electrons for pair electrons IGNE bonded/unbonded for electrons IGNE heterolytic bond breaking and bond formation (b)(iii) These marks are stand alone Trigonal ( triangular) planar/ planar with bond angles of 0º 3 3 bond pairs (no lone pairs) of electrons 3 pairs of electrons around the central atom/carbon Arranged at minimum repulsion maximum separation / distance apart Bonds or areas of electron density for pairs Just 3 pairs of electrons Just repel Repel as much as possible IGNE references to the positive charge

7 (Type of reaction:) elimination (b)(iv) dehydrohalogenation IGNE nucleophilic Product: -methylpropene methylpropene -methylprop--ene Methylprop--ene -methylprop--ene methylprop--ene any correct formula e.g. ( 3 ) 3 ( 3 ) If a displayed formula or part displayed formula is used, all the atoms must be shown. (c)(i) If a displayed formula or part displayed formula is used, all the atoms must be shown. If a carbon is clearly shown bonded to the in, penalise once in (c) 3 () 3

8 (c)(ii) 3 or Aldehydes ( 3 ) If correct carboxylic acids are shown, out of

9 3 (a) (i).x xx.x.x O.x.x xx Allow all dots / crosses, combinations of dots, crosses and other symbols like triangles Missing symbols Missing non-bonding electrons Allow extra inner electrons around carbon and /or oxygen 3 (a) (ii) Each mark is independent of the next unless the bond angle is greater than 9 o 4 09 o / 09.5 o Minimum repulsion / maximum separation (between four bond pairs of electrons / bonds) Four bond pairs give tetrahedral shape 04 o 05 o (Two) lone pairs / non-bonding pairs (of electrons) repel more (than bonding pairs)/repel a lot 3 (a) (iii) O 80 O orrect atoms in the hydrogen bond (O O) Allow 3 groups not displayed, correct ethanol formulae. ydrogen bond between methanol and water does not score ydrogen bond can be shown as dots horizontal or vertical dashes. If it is a bond-like line it must be labelled. Second mark dependent on correct atoms involved. O- O in straight line (within small tolerance) and 80 o bond angle given in the correct place

10 3 (b) (i) Any two from: Bubbles/ fizzing / effervescence (of gas) forming Sodium /solid disappearing /dissolving (to form a clear colourless solution) White solid /precipitate forming Vigorous reaction White solution/fumes form lear colourless solution forms alone 3 (b) (ii) 3 + Na 3 O ( ) Na (+) + ½ Na + as reactant 3 O Na Allow multiples, Na 3 as product, ethanol as 3 / 5 with sodium ethoxide as product, 3 NaO or Na 3 O Ignore state symbols and charges 3 (c) (i) Na r O 7 / K r O 7 / Sodium / potassium dichromate((vi)) Other oxidation numbers Allow recognisable spelling of potassium and dichromate Potassium/sodium dichromate(vi) ions If name and formula given, both must be correct. SO 4 / (Dilute / concentrated) sulfuric acid Second mark dependent on recognisably correct oxidizing agent Other acids e.g. hydrochloric, nitric, phosphoric Allow acidified / + and dichromate((vi)) / r O 7 - for mark Allow potassium manganate((vii)) and dilute sulfuric acid for mark Other oxidation numbers

11 3 (c) (ii) Reflux apparatus or reflux followed by distillation scores 0 Round-bottomed/pear shaped flask with heat Still head onical flask Open still head Delivery tube and exit above/in (cooled) collection vessel A condenser may be included Sealed apparatus (max. ) 3 (c) (iii) Mark independently Ethanal has hydrogen bonds loses first mark (Permanent) dipole dipole/permanent dipole (forces) in ethanal only Ethanal higher because both compounds have (similar) London /van der Waals /etc forces no (permanent) dipole dipole /permanent dipole (forces) in propane propane (only) has London /van der Waals /etc forces

12 4(a)(i) 4(a)(ii) 4(b) Effervescence / fizzing / bubbles (of colourless gas) Mixture gets hot White solid ( ppt) produced / sodium dissolves or disappears Any two Ignore inferences unless incorrect 4 9 ONa / 4 9 O Na + /structural or displayed formulae of any of the isomers: 3 ONa ( 3 ) ONa ( 3 ) 3 ONa 3 (ONa) 3 Structures showing a covalent bond between O and Na 4 9 NaO / 4 9 Na + O Missing hydrogen atoms Skeletal formula O Do not penalise undisplayed 3 or O- (-)methylpropan--ol Marks are stand alone 4(c) ( 3 ) correct displayed formula semi-displayed formula 3 ( 3 ) missing bracket round 3 in this version Ignore names Missing hydrogen atoms Skeletal formula

13 4(d)(i) 3 () 3 correct displayed formula semi-displayed formula Missing hydrogen atoms Skeletal formula Do not penalise missing bracket round Ignore names 4(d)(ii) O absorption / peak in -methylpropanoic acid / No O absorption / peak in Q O absorption / peak in -methylpropanoic acid / No O absorption / peak in Q Ignore references to broad or sharp peaks and to the fingerprint region 4(e) Pl 5 / Pl 3 / conc l / SOl / mixture of Nal + SO 4 / mixture of Kl + SO 4 Ignore reference to concentration of SO 4 Names ydrogen chloride onc hydrogen chloride l Pl 5 (aq), Pl 3 (aq), SOl (aq) orrect Answer Reject Mark 4(f)(i) White precipitate/ white solid 4(f)(ii) QW Water has hydrogen bonds per molecule (on average) whereas ethanol only has Water has more hydrogen bonds (per molecule) than ethanol Needs more energy to break bonds in water (so less soluble) / bonding ( intermolecular forces) stronger in water Second mark dependent on first. Ignore references to London, dispersion and van der Waals forces

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