1 (a) (CH 3 CO) 2 O + CH 3 CH(OH)CH 3 CH 3 COOCH(CH 3 ) 2 + CH 3 COOH

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1 Question er Mark Guidance 1 (a) ( 3 ) () 3 3 ( 3 ) st mark orrect structure of ester: 3 ( 3 ) 2 2nd mark Equation contains correct formulae for ( 3 ) 2, 3 () 3 AND 3 2 ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous D NT ALLW molecular formulae ALLW ( 3 ) 2 3 R ( 3 ) 2 3 (b) (i) (relative) solubility 1 IGNRE partition (ii) The esters would have similar retention times AND similar structures/molecules R same functional groups R similar polarities R similar solubilities Alcohol would have short retention time AND alkane would have long retention time 2 D NT ALLW adsorption R absorption IGNRE similar properties

2 Question er Mark Guidance (c) Elemental analysis and molecular formula 2 marks ANNTATINS MUST BE USED Working Use of percentages (to find EF) AND 144 : : = 66.63/12 : 11.18/1 : 22.19/ : : Molecular formula = marks 4 : 8 : 1 Alternative method: carbon: (144 x 66.63/100)/12 = 8 hydrogen: (144 x 11.18/100)/1 = 16 oxygen: (144 x 22.19/100)/16 = 2 ester structure 4 marks marks ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous N EF from earlier structures If not fully correct award following marks: If structure an ester of formula R the organic structure contains ( 3 ) 3 If structure is an ester of formula AND ester contains ( 3 ) 3 If structure is an ester of formula AND ester contains 2 ( 3 ) 3 AND ester contains 3 2 i.e. If the ester link is reversed IGNRE any name 3

3 Question er Mark Guidance NMR analysis 4 marks NTE: Each peak can be identified from: its δ value: ± 0.2 ppm a range, eg the peak between 2 and 3 its relative peak area (ARE two peaks have an area of 2) its splitting (ARE: two peaks are singlets) labelling on the spectrum Triplet (at δ 1.3) shows an adjacent 2 R triplet (at δ 1.3) shows ( with) 2 adjacent s/protons (because of splitting: so triplet) QW: triplet must be spelled correctly ALLW neighbouring s for adjacent to s Peak at (δ) 2.2 shows adjacent to = AND adjacent to ( with) no hydrogens (because of no splitting: so singlet) For peak at (δ) 2.2 ALLW singlet at (δ) 2.2 ALLW singlet labelled 2 Peak at (δ) 4.2 shows AND adjacent 3 R 3 adjacent s/protons (because of splitting: so quartet) Peak at (δ) 0.9 show 3 x 3 (because of singlet and area 9) 4 marks Total for 4(c) 10 Total 15 For peak at (δ) 4.2 ALLW quartet (labelled 2) heck back for any responses added to spectra ADD ^ MARK T TE SPETRUM PAGE T SW TAT IT AS BEEN LKED AT

4 Question Answer Mark Guidance 2 (a) propane-1,2,3-triol 1 ALLW absence of e after propan ALLW 1,2,3-propanetriol ALLW absence of hyphens 1, 2 and 3 must be clearly separated: ALLW full stops: R spaces: D NT ALLW (b) (i) methanol R ethanol AND renewable 1 BT points required for the mark ALLW correct structural R displayed R skeletal formula D NT ALLW molecular formulae ALLW easy/cheap to manufacture/produce as alternative for renewable/from plants/from fermentation/burns more easily/efficiently (b) (ii) equilibrium shifts to right 1 ALLW equilibrium shifts in forward direction ALLW more products form ALLW greater yield R fully reacts R goes to completion D NT ALLW improves atom economy

5 Question Answer Mark Guidance 2 (c) ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous D NT ALLW molecular formulae ( 3 2 ) ALLW further esterification, ie ( 3 2 ) ALLW linear formula for anhydride, ie If incorrect carboxylic acid/anhydride/alcohol is used, ALLW EF for second equation

6 Question Answer Mark Guidance 2 (d) A B Mark A, B and independently ie 2 column R R R R R R R R R R R R Total 8 A can be any of the alternatives in the 1st B can be any of the alternatives in the 2nd column can be any of the alternatives in the 3rd column ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous D NT ALLW molecular formulae ALLW correct names for A, B and For B accept diester For, IGNRE n R brackets (even if wrong); ALLW solid side bonds Minimum is one correct repeat unit. Polymer must be open at both ends

7 Question Answer Mark Guidance 3 (a) observation: silver R Ag ALLW black R grey type of reaction: oxidation ALLW redox organic product: ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous D NT ALLW molecular formulae ALLW carboxylate, 3 3 (b) R R intermediate R products (+ ANNTATINS MUST BE USED ALLW mechanism showing curly arrows from lone pair on and of intermediate 1 mark for curly arrow from to of = 1 mark for correct dipole on = AND curly arrow from double bond to 1 mark for correct intermediate with negative charge on AND curly arrow from to of AND curly arrow from to of 1 mark for correct organic product 4 Dipole not required on D NT ALLW incorrect dipole on ALLW 1 mark for correct intermediate with charge on AND curly arrow from to + IGNRE missing D NT ALLW incorrect second product

8 Question er Mark Guidance 3 (c) reagent: 2 D NT ALLW EF from incorrect reagent, eg 2,4-DNP observation: decolourised R orange to colourless D NT ALLW goes clear ALLW red/orange/yellow/brown in any combination organic product: ALLW organic product from reaction of one of the double bonds only, ie R ALLW correct structural R displayed R skeletal formula ALLW combination of formulae as long as unambiguous D NT ALLW molecular formulae ALTERNATIVE reagents For 1st mark, ALLW 2 R l 2 R I 2 R l R R I R 2 For 2nd mark, there must be a statement of no change R no observation or similar that implies there is no visible change EXEPT for I 2 which has an observation of decolourised R brown to colourless Total 10 For 3rd mark, correct organic product must be shown that could be from reaction of both or one of the double bonds.

9 Question Expected Answers Marks Additional Guidance 4 (a) (i) silver mirror 1 ALLW Ag(s) R Ag mirror R precipitate R ppt R solid ALLW brown R black R grey (b) (ii) 2 1 ALLW 2 R 2 2 R 2 2 R displayed R skeletal formula R 2 - D NT ALLW 2 4 R 2-hydroxyethanoic acid 2 + 3[] + 2 reagents both products 2 ALLW displayed/skeletal formula/ if molecular formula used [] max = 1 Any correctly balanced equation for partial oxidation can score 1 mark 2 + [] 2 R 2 + 2[] + 2 R 2 + [] + 2 R 2 + 2[] + 2 (c) (i) ALLW ( 2 ) 2 R ( 2 ) 2 R skeletal formula R displayed formula D NT ALLW molecular formula ( ) (ii) curly arrow from - to + dipoles and curly arrow from = bond to intermediate curly arrow from intermediate to + in 2 / + and if 2 is used it must show the curly arrow from the bond to the lone pairs are not essential 4 ALLW curly arrow to even if dipole missing or incorrect ALLW maximum of 3 marks if incorrect starting material is used See page 36 for detailed mechanisms Alternative 3 scores all 4 marks even though the intermediate is not shown

10 Alternative Alternative products are not required Alternative or Total 9

11 Question Expected Answers Marks Additional Guidance 5 (a) ALLW 2 or 1 D NT ALLW incorrect bond linkage or or (b) (i) equation ( 3 ) N ALLW ( 3 ) N N reactants ALLW 3 N N + 3 products 2 D NT ALLW molecular formulae

12 (ii) N 3 is 3 N 1 ALLW amide shown as either 3 N R 3 N R 3 N R 3 N ALLW ester shown as either 3 R 3 3 or 3 N 3 (c) (iii) to ensure t at there are no (harmful) side effects 1 ALLW impurities reduce effectiveness (of drug) R might be toxic R avoids litigation R harmful R hazardous ALLW to ensure that the drug/active component is safe IGNRE dangerous R nasty R can kill R increased dosage (aspirin contains) ester AND carboxylic acid 2 IGNRE arene or benzene or aromatic or phenyl or methyl but any other group loses the mark ALLW carboxyl group D NT ALLW acid ( paracetamol contains) amide AND phenol IGNRE arene or benzene or aromatic or phenyl or methyl but any other group loses the mark ALLW peptide ALLW hydroxy(l) D NT ALLW hydroxide or alcohol D NT ALLW amine (d) (i 3 ALLW hydrolysis by + (aq) or + or l(aq) or l or 2 S 4 (aq)

13 Na R Na - (Na + ) or 2 S 4 to give hydroxybenzoic acid + ethanoic acid with aspirin and ammonium salt of 4-aminophenol + ethanoic acid with paracetamol 3 ALLW hydrolysis by (aq) or Na(aq) and other alkali leading to hydrolysis to give carboxylate salt and phenoxide salt on the ring + ethanoate with aspirin and 4-aminophenoxide ion + ethanoate ion with paracetamol from aspirin ALLW N 3 (and 2 S 4 ) to give N 2 in one or more positions on the ring in both aspirin and paracetamol 3 D NT ALLW N 3 but correct ammonium 2 marks EF salts can be awarded N from paracetamol - (Na + ) D NT ALLW 2 but correct products can be awarded 2 marks EF if no reagent there cannot be any marks for the products If reagent selected is incorrect but would react with either aspirin or paracetamol ALLW EF for the correct organic product (ii) aspirin only Na 3 R 3 Na 2 3 R metal oxide - (Na + ) 2 ALLW Mg, carbonates, N 3 ALLW alcohols (R) to give ester if no reagent there cannot be any marks for the products 3 R If reagent selected is incorrect but would react with BT aspirin and paracetamol ALLW EF for the correct organic product (iii) paracetamol only ALLW 2 water

14 2 3 N 2 ALLW one or more at any position on the ring D NT ALLW substitution of ALLW acyl chloride or acid anhydride and corresponding ester ALLW Fel 3 to form a purple complex ion (structure not required) ALLW diazonium and structure showing azo group substituting one of the s in the ring if no reagent there cannot be any marks for the products If reagent selected is incorrect but would react with BT aspirin and paracetamol ALLW EF for the correct organic product Total 14

15 Question Expected Answers Marks Additional Guidance 6 (a) infrared 1 mark only shows (very broad) peak between (cm 1 ) (due to bond) ALLW (very broad) peak around 3000 (cm 1 ) R any stated value between 2500 and 3300 (cm 1 ) for D NT ALLW peak in range (cm 1 ) 3 IGNRE any reference to = or as both are also present in an ester R to fingerprint region 13 NMR 2 marks ( 3 ) 2 2 has 4 peaks (due to 4 different environments) ( 3 ) 3 has 3 peaks (due to 3 different environments) ALLW 13 NMR detects the number of/different environments for 1, suitable example for the 2nd mark (b) splitting pattern explains any two in terms of n + 1 rule for two marks Explains any one peak for 1 mark 6 1 mark for correct ester if two splitting patterns are correctly analysed ignore the third singlet therefore adjacent (if any) has no s multiplet R split into 7 therefore adjacent s have lots of/6 s doublet therefore adjacent is bonded to 1 ALLW singlet because next or bonded to an ALLW multiplet/heptet because next to 2 3 s ALLW doublet because next to a must spell one of multiplet / heptet, singlet, doublet correctly max = 2 marks chemical shifts ALLW tolerance on values; , and

16 two marks if any two absorptions are identified correctly one mark if any one absorption is identified correctly peak ~3.7 (ppm) bonded to an peak ~2.7 (ppm) indicates it is next to a = (ppm) ALLW any two gets 2 marks, any one scores 1 mark R 3.7 (ppm) 2.7 (ppm) 1.2 (ppm) peak ~1.2 (ppm) bonded to other s R part of a chain max = 2 marks ALLW peaks labelled on the spectrum ALLW singlet must be bonded to, multiplet to = and doublet to or R for both chemical shift marks if two chemical shifts are correctly identified IGNRE the third compound identified as ( 3 ) marks compound identified as 3 ( 3 ) 2 1 mark Total 9

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