Hydroxy compounds

10(a) C H O– / C H O–Na+ / C H ONa [1] 4 6 5 6 5 6 5 C H O– / C H O–Na+ / C H ONa [1] 6 5 6 5 6 5 C H N C H O– 6 5 2 6 4 or C H N C H OH or 6 5 2 6 4 [1] C H OCOC H CO C H [1] 6 5 6 4 2 6 5 10(b) 2 and 4 [1] 1 © UCLES 2021 Page 12 of 12

4(a)(i) In F: (phenyl)amine AND carboxylic acid 2 In J: phenol AND ester Any two for one mark All four for two marks 4(a)(ii) 0 (zero) in F AND 2 (two) in J 1 © UCLES 2022 Page 8 of 12 4(b)(i) step 1 CH Cl AND AlCl [1] 3 3 3 step 2 D = [1] step 4 (hot) Sn AND concentrated AND HCl [1] 4(b)(ii) 2 [1] COOH group is electron-withdrawing group and 3,5-/meta- directing [1] 4(c)(i) C H O 1 9 18 4(c)(ii) hydrolysis [1] 2 acid–base / neutralisation [1] 4(d)(i) C H OH + Na → C H O(–)Na(+) + ½H 1 6 5 6 5 2 4(d)(ii) 1 4(d)(iii) • (CO)O—H bond weaker / more easy to donate H+ in K 2 • owing to negative inductive / electron withdrawing effect of C=O / COOH group • carboxylate anion stabilised / phenoxide anion is less stabilised All three for two marks © UCLES 2022 Page 9 of 12 4(e) p-orbital on oxygen overlaps with ring / π system OR lone pair of e– on oxygen is delocalised into the ring [1] 3 electron density in ring increases [1] attracts/polarises electrophile better [1] Question Answer Marks

7(a) M1 p-orbital / lone pair from O atom is overlaps / delocalised into the ring 3 M2 greater  electron density around the ring OR makes the ring more electron rich / positions 2,4,6 more electron rich M3 polarises electrophiles more easily 7(b) iodobenzene AND as Br is more electronegative (than I / I+/I+ in the electrophile) 1 7(c)(i) C H O / C H OH + Na  C H O–Na+ + ½H 1 6 6 6 5 6 5 2 7(c)(ii) 1 © UCLES 2023 Page 15 of 19 7(c)(iii) M1 reaction 1: aqueous HNO / dilute HNO 2 3 3 M2 reaction 2: alkaline/ NaOH AND C H N + (Cl–) 6 5 2 OR alkaline / NaOH AND benzene / phenyl diazonium ion / salt Question Answer Marks

9(a)(i) C H OH + Na → C H ONa + ½H 1 6 5 6 5 2 9(a)(ii) 1 both structures for one mark 9(b) 3 M1 correct dipole AND curly arrow from inside the hexagon to the carbon atom M2 structure of the intermediate M3 curly arrow from C-H bond into the ring AND H+ © Cambridge University Press & Assessment 2024 Page 17 of 18 9(c)(i) 1 All three curly arrows for one mark 9(c)(ii) 1 © Cambridge University Press & Assessment 2024 Page 18 of 18

9(a)(i) C H OH + Na → C H ONa + ½H 1 6 5 6 5 2 9(a)(ii) 1 both structures for one mark 9(b) 3 M1 correct dipole AND curly arrow from inside the hexagon to the carbon atom M2 structure of the intermediate M3 curly arrow from C-H bond into the ring AND H+ © Cambridge University Press & Assessment 2024 Page 17 of 18 9(c)(i) 1 All three curly arrows for one mark 9(c)(ii) 1 © Cambridge University Press & Assessment 2024 Page 18 of 18

8(a) M1: p orbital / lone pair on the oxygen / O 2 AND is delocalised into the ring / overlaps with delocalised ring [1] M2: O-H weakened (in phenol) OR anion / phenoxide ion / conjugate base is stabilised/more stable [1] 8(b)(i) 2,4,6-tribromophenol (name) AND hydrogen bromide / HBr [1] 1 © Cambridge University Press & Assessment 2024 Page 13 of 14 8(b)(ii) 1 AND 8(b)(iii) 2C H OH + 2Na → 2C H ONa + H [1] 1 6 5 6 5 2 8(c) step one: HNO (+ HCl) OR NaNO + HCl 2 2 2 AND T⩽10 °C step two: H O 2 AND warm / T> 10 °C any two [1] all four [2] © Cambridge University Press & Assessment 2024 Page 14 of 14

8(a) M1: p orbital / lone pair on the oxygen / O 2 AND is delocalised into the ring / overlaps with delocalised ring [1] M2: O-H weakened (in phenol) OR anion / phenoxide ion / conjugate base is stabilised/more stable [1] 8(b)(i) 2,4,6-tribromophenol (name) AND hydrogen bromide / HBr [1] 1 © Cambridge University Press & Assessment 2024 Page 13 of 14 8(b)(ii) 1 AND 8(b)(iii) 2C H OH + 2Na → 2C H ONa + H [1] 1 6 5 6 5 2 8(c) step one: HNO (+ HCl) OR NaNO + HCl 2 2 2 AND T⩽10 °C step two: H O 2 AND warm / T> 10 °C any two [1] all four [2] © Cambridge University Press & Assessment 2024 Page 14 of 14

5(a) sp2 = 6 / six sp3 = 3 / three 1 © Cambridge University Press & Assessment 2025 Page 10 of 14 5(b)(i) electrophilic substitution 1 5(b)(ii) AlBr 3 1 5(b)(iii) 3 + H+ M1: curly arrow from inside the hexagon ring AND towards positively charged carbon atom (in the electrophile (CH ) CH +) 3 2 M2: structure of the intermediate M3: curly arrow from C–H bond into the ring AND formation / loss of H+ 5(b)(iv) 2° carbocation / (CH ) CH+ 1 3 2 AND is more stable due to greater positive inductive effect (of alkyl groups) 5(c)(i) S = 146 + 200 – 205 – 278 = –137 (J K–1 mol–1) 1 5(c)(ii) G = H – TS AND T = 298 / 298.15 used 2 G = –371 – (25+273)(–0.137) = –330 (kJ mol–1) [so feasible] ecf M1 5(d)(i) M1: conditions for phenol = 4 • aqueous / aq • bromine water • no AlBr needed 3 M2: lone pair (of e–)/p-orbital on oxygen AND overlap / delocalised with ring /  system M3: electron density in ring increases / ring becomes more electron rich (and attracts electrophiles) M4: (phenol is more reactive so) polarises Br / bromine / electrophiles more 2 © Cambridge University Press & Assessment 2025 Page 11 of 14 5(d)(ii) 1 Q = 5(d)(iii) 1 R = / / benzene diazonium chloride 5(d)(iv) azo 1 5(d)(v) structure / name of 2-nitrophenol and 4-nitrophenol 2 —OH / hydroxyl group is electron donating group AND 2,4-directing / ortho / para directing © Cambridge University Press & Assessment 2025 Page 12 of 14

6(a)(i) HNO + H SO → NO + + HSO – + H O 1 3 2 4 2 4 2 OR HNO + 2H SO → NO + + 2HSO – + H O+ 3 2 4 2 4 3 © Cambridge University Press & Assessment 2025 Page 11 of 17 6(a)(ii) 3 M1: curly arrow 1 from inside the hexagon to nitrogen of NO + 2 M2: intermediate, usual rules for horseshoe and + charge M3: curly arrow 2 from C-H bond into hexagon AND H+ 6(b) M1: p-orbital/lone pair from O / oxygen AND is delocalised / overlaps AND into the ring /  system 2 M2: so electron density of the ring is increased OR polarises electrophiles / NO + better 2 6(c) 1 6(d)(i) (hot) tin / Sn AND concentrated AND HCl 1 6(d)(ii) reduction 1 © Cambridge University Press & Assessment 2025 Page 12 of 17 6(d)(iii) 1 6(d)(iv) (nucleophilic) addition – elimination 1 6(e) M1: 2-nitrophenol  phenol  water  ethanol 4 M2: weakens O—H bond / anion stabilised AND proton/H+ (more easily) lost / proton / H+ (more easily) donated M3: (for 2-nitrophenol / phenol), a p-orbital / lone pair from O / oxygen AND is delocalised / overlaps AND into the ring /  system (and increases electron density in the ring) M4: (for ethanol), positive inductive effect / electron donating of alkyl group 6(f)(i) 2 name of functional group classification of functional group alcohol / hydroxyl primary alcohol / hydroxyl secondary amine secondary Any three correct [1] all six correct [2] © Cambridge University Press & Assessment 2025 Page 13 of 17 6(f)(ii) 1 6(f)(iii) 1 Question Answer Marks

7(a) M1: (most acidic) benzoic acid 4 4-methylphenol water (least acidic) phenylmethanol M2: correct link of acidity to weakens O—H / H+ more easily lost / anion stabilised / conjugate base stabilised M3 and M4: any two [2] • for benzoic acid: negative inductive effect of C=O / electronegative C=O / two electronegative O / –ve charge delocalised (across two O) / resonance in –COO– • for 4-methylphenol: as lone pair on oxygen delocalised into the ring /  system / delocalised system OR p orbital on oxygen overlaps with ring /  system / delocalised system • for phenylmethanol: positive inductive effect of alkyl group / R / CH 2 7(b) 1 7(c)(i) 1 7(c)(ii) (reaction 10) addition–elimination / condensation / esterification 1 AND (reaction 11) addition–elimination / condensation (polymerisation) / esterification © Cambridge University Press & Assessment 2025 Page 14 of 16 7(c)(iii) 2 M1: ester linkage shown M2: rest of the structure correct with continuation bonds Question Answer Marks

7(a)(i) HNO and H SO and conc once and 25° ⩽ T ⩽ 60° 1 Acids may be named. 3 2 4 Any dilute or aq is CON. Temperature must be numerical and within range. I heat or warm. CON boil or reflux. 7(a)(ii) 0° ⩽ T ⩽ 10° and 1 A ‘T below 10o’ etc. CON heat or warm. HNO or NaNO + HCl I sodium nitrate. 2 2 A nitrous acid. 7(a)(iii) benzenediazonium chloride / phenyl diazonium chloride 1 A very minor errors, e.g. word order. CON benzyl’benzoyl. I diazo. 7(b)(i) 0 1 2 1 A blank for zero. 0 6 3 7(b)(ii) 6 1 Trace ID: PC-F9EA0E463D Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a1 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/41 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(iii) 1 I + on the H+. Curly arrow must start on C=O. Any incorrect curly arrow is CON. A in two steps, e.g. dipole with dipole. Curly arrow from C=O to H+ Additional charges are CON. or © Cambridge University Press & Assessment 2026 Page 15 of 21 Trace ID: PC-F9EA0E463D Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a1 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/41 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(iv) 3 ‘Usual rules’ for K. Centre of + charge must be above a line joining C3 and C5. ‘Horseshoe’ must include C6, C1 and C2, may include one or both of C3 and C5, must not include C4. I curly arrow showing delocalisation of phenolic LP (LP on oxygen of phenol). CON additional curly arrows M1 CA on leftmost diagram Curly arrow must start on or within hexagon and may cross hexagon M2 K, showing horseshoe, + charge and H anywhere. M3 curly arrow on C–H bond in K back into ring Curly arrow must touch hexagon. Use of quinoid intermediate: M1 as above – curly arrow on leftmost diagram M2 for the intermediate shown at the bottom of guidance. The curly arrow for M3 is shown on this diagram but is not necessary for M2. M3 as above – curly arrow on C–H bond in K back into ring © Cambridge University Press & Assessment 2026 Page 16 of 21 Trace ID: PC-F9EA0E463D Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a1 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/41 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(v) • less readily 2 ⚫✓⚫✓ two points for one mark, • lone pair (LP) on O (of phenol) / p-orbital on O four points for two marks. • is delocalised into the ring / overlaps with delocalised ring / -system A LP on OH I LP in phenol. • activates ring / more attractive to electrophile / electron (charge) density ‘Delocalised’ or ‘joins  system’ needed increased (‘electron’ inferred if ‘LP donated to ring’) / becomes more may be awarded without LP if linked to O. electron rich I references to polarisation of electrophile (it has a full + charge, stated in the Q) I makes ring more reactive / more susceptible to electrophiles / more negative. I ‘O is electron donating’. I ‘attracts nucleophile more’. 7(c)(i) 2 A OH of tertiary alcohol group substituted to bromide as well as ring substitutions and equation with HBr and H O on the 2 right. + 2Br → + 2HBr 2 M1 structure of product (compound H) M2 equation balanced, must have HBr → product above + H O + HBr 2 7(c)(ii) electrophilic substitution 1 CON nucleophilic substitution unless –OH on sidechain substituted with Br when it scroll and SEEN becomes I. © Cambridge University Press & Assessment 2026 Page 17 of 21 Trace ID: PC-F9EA0E463D Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a1 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/41 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/

6(a)(i) Observations: 1 A initial colour brown / yellow for ‘orange’ and white ppt. variants of these. and (solution) decolourises / turns colourless / orange colour disappears CON fizzing. I steamy fumes. I discolouration / colour discharged. I ‘colour disappears’. 6(a)(ii) 1 structure 6(b) M1 lone pair on oxygen / O delocalised / overlaps 2 I donated / incorporated in reference to and into the ring /  system / delocalised system ‘delocalised / overlaps’. or p-orbital on oxygen / O delocalised / overlaps and with ring /  system / delocalised system [1] I ‘H+ more easily lost’ for more acidic. M2 weakens O—H and phenol is more acidic or (phenol forms) anion / conjugate base / phenoxide ion is more I O–H is weak alone – comparison needed. stable and phenol is more acidic [1] A phenol is a stronger (acid) for ‘more acidic’. 6(c)(i) 1 I connectivity errors to COOH. Phenol must be 1,2-substituted and drawn. Fully skeletal structures must have brackets if solid line continuation bonds . © Cambridge University Press & Assessment 2026 Page 18 of 25 Trace ID: PC-9D76E91B48 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a2 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/42 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 6(c)(ii) 2 A M2 if structure (partly / fully) displayed / all the carbons shown with ‘–’ continuation bond. If structure fully skeletal: continuation bonds – must be dashed / wavy / different or have through brackets. Phenol must be 1,2-substituted and drawn. M1 ester linkage shown between phenol & COOH [1] M2 rest of the structure correct [1] DEP on M1 6(d) 2 A M1 for LiAlH reduction [conjugated 4 unsaturated carboxylic acid]. M1M2 © Cambridge University Press & Assessment 2026 Page 19 of 25 Trace ID: PC-9D76E91B48 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a2 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/42 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 6(e)(i) D E 2 D and E are unconditional. OH O OH OH CH 3 O OR O CH 3 CH O 3 O CH 3 M1M2 6(e)(ii) Mark based on 6(e)(i) 3 A CH Br / CH I for alkylation. 3 3 step 1 CH Cl (and AlCl ) [1] CON (aq), I any halogen carrier for alkylation. 3 3 CON other reagents I heat / any temp for alkylation & acylation. step 2 hot / reflux / heat / boil / T ⩾ 60 °C and (alkaline / acidified / neutral) MnO – / KMnO [1] CON use of KMNO for oxidation. 4 4 4 CON (aq) once only then apply ecf. step 3 CH COCl [1] CON (aq) CON UV for acylation. 3 CON any other reagent e.g. cH SO 2 4 © Cambridge University Press & Assessment 2026 Page 20 of 25 Trace ID: PC-9D76E91B48 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a2 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/42 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/

7(a)(i) HNO and H SO and conc once and 25° ⩽ T ⩽ 60° 1 Acids may be named. 3 2 4 Any dilute or aq is CON. Temperature must be numerical and within range. I heat or warm. CON boil or reflux. 7(a)(ii) 0° ⩽ T ⩽ 10° and 1 A ‘T below 10o’ etc. CON heat or warm. HNO or NaNO + HCl I sodium nitrate. 2 2 A nitrous acid. 7(a)(iii) benzenediazonium chloride / phenyl diazonium chloride 1 A very minor errors, e.g. word order. CON benzyl’benzoyl. I diazo. 7(b)(i) 0 1 2 1 A blank for zero. 0 6 3 7(b)(ii) 6 1 Trace ID: PC-F2CDA313A1 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a3 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/43 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(iii) 1 I + on the H+. Curly arrow must start on C=O. Any incorrect curly arrow is CON. A in two steps, e.g. dipole with dipole. Curly arrow from C=O to H+ Additional charges are CON. or © Cambridge University Press & Assessment 2026 Page 15 of 21 Trace ID: PC-F2CDA313A1 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a3 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/43 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(iv) 3 ‘Usual rules’ for K. Centre of + charge must be above a line joining C3 and C5. ‘Horseshoe’ must include C6, C1 and C2, may include one or both of C3 and C5, must not include C4. I curly arrow showing delocalisation of phenolic LP (LP on oxygen of phenol). CON additional curly arrows M1 CA on leftmost diagram Curly arrow must start on or within hexagon and may cross hexagon M2 K, showing horseshoe, + charge and H anywhere. M3 curly arrow on C–H bond in K back into ring Curly arrow must touch hexagon. Use of quinoid intermediate: M1 as above – curly arrow on leftmost diagram M2 for the intermediate shown at the bottom of guidance. The curly arrow for M3 is shown on this diagram but is not necessary for M2. M3 as above – curly arrow on C–H bond in K back into ring © Cambridge University Press & Assessment 2026 Page 16 of 21 Trace ID: PC-F2CDA313A1 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a3 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/43 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/ 7(b)(v) • less readily 2 ⚫✓⚫✓ two points for one mark, • lone pair (LP) on O (of phenol) / p-orbital on O four points for two marks. • is delocalised into the ring / overlaps with delocalised ring / -system A LP on OH I LP in phenol. • activates ring / more attractive to electrophile / electron (charge) density ‘Delocalised’ or ‘joins  system’ needed increased (‘electron’ inferred if ‘LP donated to ring’) / becomes more may be awarded without LP if linked to O. electron rich I references to polarisation of electrophile (it has a full + charge, stated in the Q) I makes ring more reactive / more susceptible to electrophiles / more negative. I ‘O is electron donating’. I ‘attracts nucleophile more’. 7(c)(i) 2 A OH of tertiary alcohol group substituted to bromide as well as ring substitutions and equation with HBr and H O on the 2 right. + 2Br → + 2HBr 2 M1 structure of product (compound H) M2 equation balanced, must have HBr → product above + H O + HBr 2 7(c)(ii) electrophilic substitution 1 CON nucleophilic substitution unless –OH on sidechain substituted with Br when it scroll and SEEN becomes I. © Cambridge University Press & Assessment 2026 Page 17 of 21 Trace ID: PC-F2CDA313A1 Re-uploading, mirroring or re-hosting this file on any other website or domain is unauthorised and traceable. Licensed for hosting on papacambridge.com only. P97a01p/4a3 CMaarkm Scbhermide gJuene 2·0 2p6 a| Spoaurccea: mpapbarciadmgbreid.gceo.comm 9701/43 Mark Scheme June 2026 Downloaded from PapaCambridge - https://papacambridge.com/