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CIE Nov 2014 v3 Paper 4 Q6
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![Methoxetamine is a derivative of the pharmaceutical drug, ketamine. 12 PMT OCH3 NHCH2CH3 methoxetamine (a) (i) What is the molecular formula of methoxetamine?(ii) On the diagram above, circle any chiral centres that are present in methoxetamine. (iii) Name two functional groups in methoxetamine, in addition to the aryl group.[4]UCLES 2014 9701/43/O/N/14<br />
(b) In the table, complete the structure of each of the compounds formed when methoxetamine is reacted with the following reagents. State the type of reaction in each case. 13 PMT reagent (i) LiAl H4 (ii) HCl (aq) (iii) CH3COCl structure of product type of reaction OCH3 OCH3 OCH3 [6] [Total: 10]UCLES 2014 9701/43/O/N/14 [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/November_2014_v3_QP_-_Paper_4_CIE_Chemistry_A-level_6-0.jpg)
![Page 6 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 43 (b) Reagent X e.g. Br2, HNO3, Na, NaOH, benzenediazonium salt / ion; RCOCl ; Fe 3+ ; H2+Ni substituted product for L-DOPA & vanillin (examples given are for X = Br2 and NaOH) Br Br OH OH OH or NH COOH CO NH OH CO Reagent Y e.g. HCl; Na2CO3, Mg, SOCl 2, PCl 5, ROH + c.H2SO4; HCl+NaNO2 / HNO2; CH3Cl Correct substituted product for L-DOPA OH OH NH COOH Reagent Z e.g. acidified Cr2O7 ; 2,4-DNPH, hydrazine ; Fehlings, Tollens; HCN; HCN + NaCN; 2 NaBH4 ; correct substituted product for vanillin OH OH OH PMT [7] (a) (i) C15H21NO2Cambridge International Examinations 2014<br />
Page 7 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 43 (ii) OCH NHCH CH (iii) any two of ketone, amine or ether [4] PMTCambridge International Examinations 2014<br />
Page 8 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 43 (b) (i) LiAlH4 OH OCH reduction / nucleophilic addition (ii) HCl (aq) NHCH CH OCH acid-base / neutralisation NH CH CH (Cl - ) (iii) CH3COCl OCH acylation / condensation allow addition + elimination allow nucleophilic substitution COCH CH 1 mark for each correct structure 1 mark for each correct reaction typeCambridge International Examinations 2014 PMT [6]<br />](https://learnah.org/wp-content/uploads/2018/08/November_2014_v3_MS_-_Paper_4_CIE_Chemistry_A-level_6-0.jpg)
