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CIE Jun 2014 v3 Paper 4 Q4
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![Noradrenaline is a hormone and neurotransmitter, which is released during stress to stimulate the heart and increase blood pressure. 10 PMT HO HO OH NH2 noradrenaline (a) State the names of three functional groups in the noradrenaline molecule.[3] (b) (i) Consider the following two-stage synthesis of noradrenaline from dihydroxybenzaldehyde. HO step 1 HO dihydroxybenzaldehyde OH NH2 step 2 HO HO noradrenalineDraw the structure of the intermediate Z in the box. Suggest reagents for steps 1 and 2. step 1step 2UCLES 2014 9701/43/M/J/14<br />
PMT 11 (ii) Dihydroxybenzaldehyde reacts with Br2(aq).Describe what you would see during this reaction.Draw the structure of the product. (c) Draw the structures of the products when noradrenaline is reacted with (i) dilute NaOH(aq), (ii) dilute HCl (aq), (iii) an excess of ethanoyl chloride, CH3COCl. [5] [4] (d) Name the new functional groups formed in the reaction in (c)(iii).[2]UCLES 2014 9701/43/M/J/14 [Total: 14] [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/June_2014_v3_QP_-_Paper_4_CIE_Chemistry_A-level_4-0.jpg)
![Page 4 Mark Scheme Syllabus Paper GCE A LEVELMay/June 2014 9701 43 PMT (ii) must be skeletal trans-cis CO (iii) OH cis-trans OH cis-cis OH [1] [1] [1] [1] [1] [1] [1] 2 mol dm 3 [1] [1] [1] [1] [1] + CO or HO C-CO [1] [1] (c) (i) Kw = [H ][OH 3 (ii) In 0.15 mol dm / [OH ] = Kw [H 3 - NaOH, [OH ] = 0.15 mol dm ], so [H ] = 110 14 / 0.15 = 6.6710 14 mol dm 3 pH = -log10[H ] = 13.18 (13.2) ecf from [H (iii) piperidine is a poorer proton acceptor or piperidine is partially ionised (iv) piperidine should be a stronger base/more basic than ammonia because of the electron-donating (alkyl/CH2) groups (d) (i) n(HCl) at start = 0.120/1000 = 2.010 3 mol n(HCl) at finish = 2101.510 = 0.0005/510 3 3 4 mol 3 (ii) this is in 30 cm of solution, so [HCl] at finish = 0.510 /0.030 = 1.6710 pH = log10(1.6710 ) = 1.78 ecf from (d)(i) 2 (iii) pH / vol curve: start at pH 11.9 vertical portion at V = 15 cm levels off at pH 1.8 (iv) indicator is B [Total: 16] (a) three from phenol (secondary) alcohol (primary) amine arene / aryl / benzene 3[1]Cambridge International Examinations 2014<br />
Page 5 Mark Scheme Syllabus Paper GCE A LEVELMay/June 2014 9701 43 (b) (i) HO HO Compound Z is OH CH CN step 1: HCN + NaCN or HCN + base step 2: H2 + Ni or LiAlH4 or Na + ethanol PMT [1] [1] [1] (ii) bromine decolourises or goes from orange to colourless or white ppt. formed [1] Br HO CHO e.g. (2 or 3 x Br in ring) 2 or 3 bromines in ring HO Br [1] (c) (i) (i) (ii) (ii) (iii) (iii) NaO NaO HO HO OH NH (or ionic) [1] [1] OH NH Cl NH (or ionic) [1] [1] CH COO NHCOCH OCOCH CH CO M1: amide M2: alcoholic ester M3: both phenolic esters (d) amide ester [1] [1] [1] [5] max [4] [1] [1] [Total: 14]Cambridge International Examinations 2014<br />](https://learnah.org/wp-content/uploads/2018/08/June_2014_v3_MS_-_Paper_4_CIE_Chemistry_A-level_4-0.jpg)
