4.4, 4.5 HW MS 1. (a) nucleophilic addition 1 M2. (b) (i) 2-hydroxybutanenitrile 1 (ii) 2 H 3C O H

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1 4.4, 4.5 W MS 1. (a) nucleophilic addition 1 M N N M1 M M4 4 (b) (i) -hydroxybutanenitrile 1 (ii) N (allow 1 for amide even if not 4 7 N, i.e. RN ) (if not amide, allow one for any isomer of 4 7 N which shows geometric isomerism) (c) (i) 1 (ii) 1 (iii) = 1 [11] Mill ill igh School 1

2 . (a) (i), dimethylbutan ol (ii) elimination Mechanism ( ) ( ) ( ) ( ) (iii) ( ) Structure ( ) ( ) ( ) ( ) Name of isomer, dimethylbut 1 ene Explanation loss of or from end also possible 10 (b) (i) Equation ( ) ( ) l ( ) ( ) l Name of mechanism addition elimination Mechanism l l R : R allow loss of here R (ii) Type of reaction esterification Reagent(s) or ethanoic acid onditions strong acid catalyst or S 4 or L 9 [19] Mill ill igh School

3 . (a) (i) propyl methanoate not propanyl Test bservation with observation with D A wrong reagent or no reagent scores zero An incomplete reagent such as silver nitrate for Tollens, or potassium dichromate loses the reagent mark, but can get both observation marks penalise observations which just say colour change occurs or only state starting colour (ii) Reagent: Na bservation with : no reaction bservation with D: effervescence 4 for and D NT Tollens an identified (hydrogen) carbonate acidified K r 7 acidified KMn 4 no reaction goes green goes colourless bubbles or correct metal no reaction no change no change bubbles or UI or stated indicator no change red or correct colour p 6.9 Pl 5 no reaction (misty) fumes (b) (i) Reagent: pentan--one or -pentanone but not pent--one or pentyl (ii) Reagent: Tollen s or Fehling s bservation with E: no reaction bservation with F: silver mirror or red ppt 4 for E and F Test Tollens Fehlings or Benedicts observation with E observation with F iodoform or I /Na acidified K r 7 Schiff s no reaction no reaction yellow (ppt) no change no reaction silver or mirror or grey or ppt red or ppt not red solution no reaction goes green goes pink (c) 1 must be aldehyde. Allow 5 for otherwise this is the only answer [9] Mill ill igh School

4 4. (a) (i) B: propanoyl chloride (or consequentially on part (a) (ii)) : propanoic anhydride (or consequentially on part (a) (ii)) do not allow formulae (ii) effervescence / misty fumes / steamy fumes / fumes / solution becomes warm / fizzing not just gas 1 (iii) N 1 (the minimum necessary for the mark is = and N shown) (iv) ( ) 1 allow 5.. (b) (i) methanol methyl propanoate (or consequentially on part (a) (ii)) do not allow formulae (ii) A: in presence of (concentrated) sulphuric acid / S 4 / strong acid / gaseous hydrogen chloride or l allow dilute S 4 heat / reflux (but only if first mark awarded) allow 1 mark for acidic conditions / and heat B: room temperature / in the cold / not heated / cooling not acid : heat / reflux not acid 4 [11] 5. (a) (i) eq n (ii) ester solvent, flavourings (iii) conc S 4 in same physical state 6 (b) Mill ill igh School 4

5 (c) (i) (ii) two on carbon in double bond (iii) = or cis but--ene trans but--ene 7 [14] 6. (a) Reagents NaB 4 Type of reaction reduction (b) (i) Reagents(s) K r 7 S 4 onditions reflux (ii) [] 4 (c) Reagents N or NaN/ Name of mechanism nucleophilic addition (d) (i) mirror images (ii) plane polarized light rotated in opposite directions (e) (i) Structure (ii) Name propyl propanoate (f) or 6 4 [16] Mill ill igh School 5

6 7. (a) (i) correct graphical formula for tertiary alcohol allow not 5 -methylbutan--ol / -hydroxy--methylbutane / -methyl- -hydroxybutane award name mark even if it follows incorrect formula (ii) graphical formula of pent-1-ene graphical formula of pent--ene accept geometrical isomers of pent--ene if clearly shown to be different (iii) dehydration / elimination 1 (iv) no atoms on atom next to / three methyl groups on 1 (b) (i) ethanenitrile / ethanonitrile / methyl cyanide / cyanomethane / acetonitrile 1 (ii) any hydrolysis 1 (iii) l N N l for correct formula of methylamine / l product overall correct [10] 8. (a) NaB 4 1 (b) nucleophilic addition : N :N 5 (c) (i) hexanedioic acid (ii) Mr = 98 Mr = g =.58 g 98 4 [10] 9. (a) (i) ethyl ethanoate (ii) esterification / condensation / addition - elimination 1 Mill ill igh School 6

7 (b) (i) aqueous / dilute sulphuric / hydrochloric acid (allow l(aq); S 4 (aq) not water) temp. < 100 / warm / heat / reflux (this mark dependent on sensible reagent) (ii) 5 5 (allow 4 8, 4 but must have 5 ) 1 (c) (i) sodium hydroxide / sodium carbonate / sodium hydrogen carbonate (allow formula) room temperature / aqueous (nd mark dependent on correct reagent) (ii) ethanoic anhydride (methyl groups can be shown as but the bond must be drawn) (iii) addition of water / hydrolysis ( ) (d) (i) ethanamide not ethylamide. N (ii) ammonia (not if dilute implied) / ammonium carbonate /Pl 5 followed by N (allow formulae) heat or temperature < 100 (iii) N l N 4 l 1 [17] Mill ill igh School 7

8 10. (a) (i) An appropriate alkene; or ( ) 1 Isomer 1 1 Isomer 1 Position isomerism 1 Mechanism electrophilic attack and electron shift to Br (Unless used) 1 carbocation 1 reaction with carbocation 1 [Allow mechanism marks for the alkene ] [Allow one mark if mechanism for minor product given] (ii) An appropriate carbonyl; 1 Mechanism nucleophilic attack and electron shift to 1 anion intermediate 1 reaction with anion 1 [Allow mechanism marks for the carbonyl ( ) ] Isomer 1 1 Isomer 1 ptical isomerism 1 NB NB Isomer structures must be tetrahedral Penalise stick structures once in part (a) (b) QoL Large charge on carbonyl carbon atom due to bonding to and l 1 Nucleophiles have electron pairs which can be donated 1 Equation Species 1 Balanced 1 [18] Mill ill igh School 8

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