A2 CHEMISTRY TOPIC 4.1.1 ARENES TOPIC 4.1.2 CARBONYL COMPOUNDS TOPIC 4.1.3 CARBOXYLIC ACIDS AND ESTERS BOOKLET OF PAST EXAMINATION QUESTIONS PART II TOTAL 80 MARKSa 6 (a) Esters aro well known as compounds providing the flavour in many fruits and the scent of some flowers. The ester CH,(CH,),COOCH, contributes to the aroma of apples. () © Name the ester CH,(CH,),COOCH,. 0] G11) Stte the reagents anc conatons for the hycolsis ofthis ester inte laboratory. (3) (b) Leaf alcohol, B, is a stereoisomer that can form when insects eat leaves. eae aN . Paes Cy H H (i) Draw the skeletal formula of B, a G_ A Brew ne geomotnc somer of 8. (1)7 (ili) Draw a structure for the ester expected when B reacts with ethanoic acid in the presence of an acid catalyst. Show all the bonds in the ester group. (2) (ce) A chemist analysed a sample of B and determined its M, value () Deduce the M, value that the chemist would expect for leaf alcohol. expected M, (ii) What technique could the chemist have used to determined the M, for leaf alcohol? M1 (iii) A chemist reacted B to form a product C with an M, 18 units less than that of B. ‘Suggest a structrure for C and deduce the type of reaction that took place. structure of C - 2] [Total : 12] a type Of reaction sree Erannar amesue [Turn over12 6 Like esters, carbonyl compounds can contribute to the smell of plants and food. The carbonyl compounds D and E are structural isomers. (@) 6 D CH,COCH, E CH,CH,CHO Name compounds D and E. oo (I) ssereasene Slate the reagents you would use and the observations you would make for a simple chomical test (i) inwhich D and E behave in the same way; reagont(s) observation .. ee (1!) which can be used to distinguish between D and E. reagent(s) ‘observation for D ‘observation for E » [3] Exsmvers13 a (e)_ The infrared spectrum of D is shown below. 0 absorbance/% gs 100: 4000 Tory T 7 T 1 3000 2000 1500 1000 500 wavenumber/em (1) On the spectrum above, mark with a cross the absorption peak that identfies the functional group. Explain how you made your choice. (Use the Data Sheet provided to answer this question.) “2 (i) Reduction of compound D with NaBH, produces a compound with the molecular formula CgH,O- How would the infrared spectrum of this product be differant from that of D2 + 2] For xame ssn [Turn over4 For exaave 3 Acommorcial synthesis of the ester G is shown below. ‘CH,COOH, cone. H,S0, (C,H,CH,CI — —> ,H,CH,OH ——*—* > ©,H,CH,COOCH,, stage I stage IT E F 6 (@) Stage I: © @ Suggest a suitable reagent. a (ii) State the type of reaction occurring. (lil) Write the equation for this reaction. {b) Stage Il: (I) Draw the displayed formula for the ester G. (i) Write the equation. (iil) Suggest a general use for ostors such as G. 6 ( can also be made diréctly from E by reaction with CH,COO"Na*. Suge: [pOBsiblg mechanism for this reaction. rR [Total m6 Compounds K and L are structural Isomers, CH,OH ‘OCH, K L (@) (I) Whatis the molecular formula of these isomers? vo Uf] BD {il) Calculate the mass:charge ratio, m/e, you expect for the molecular ion peak in the ae mass spectrum of K, showing your working, Answer Oi (itl) A sample of L is sent for analysis to determine its percentage by mass of carbon ‘and hydrogen, Calculate the expected results, %C %H 2 }) Explain how infra-red spectra would allow you to distinguish between samples of K and L. raussvoe For Examines Use40 7 Complete the reaction schemes below. Draw the structural formula of an appropriate organic compound, or give a sultable reagent, in each of the boxes provided. Toller’s reagent {ammoniacal Oo (a)roro duesatteey Oa Hee cone. HO, and conc, HNO, (pr EEE err Oe 7 a f) arnt Oo (©) CoHy TT CCF ‘Sn and gone, HCL 8 (oS HAS. a heat [eae eee reece] ri NaOH 6 (») SRO NON > CHyCOO-Nat + CgH,OH Geran heat 1" HCNandKON = [ QO of mechanism. se sue For rane.10 5 Compounds with the formula C,H,OH are alcohols. (a). Draw formulae to show the four structural isomers of alcohols with the molecular formula CyHj00. 4 (b) One of the isomers in (a), compound D, reacts with K,Cr,0, in tho presence of H,S0,, togive E. ‘When E is heated with ethanol in the presence of concentrated H,SO,, compound F is formed. ° Kero, cone. He SO, ‘othanol, cone, HSO, heen Pec eLecrig ge HCC _CHCHy heat heat CH 0 bay abe" © (inthis question, one mark is available for the quality of written communication. Stato the reaction, if any, of each of your alcohols in (a) with acidified K,Cr,0,. Use this information and the reactions above to identify D and E. Give your reasoning. {81 Quality of Wiitten Communication [1] (ii) Write the equation for the formation of F from E. [1] {c) Compound F and compound @ (shown betow) are both esters. Draw the structure of the product of the reaction of G with hot, aqueous NaOH. He Heo 8 { i hot NaOH(aq) HAC. 0 reer ~s He Ga a) [Total: 13] tes [Turn over Fo13 [© 2Hyetonyprenanoe acid was desoWved in D,0 and an num. spectrum of the solution asons, the splitting patterns observed in this spectrum. was taken, Predi (ec) Hopt-4-enai, H, is also present in milk. (i) Doduce the molecular formula of H. Bo Draw the skeletal formula of a stereoisomer of H. Oo (iil) Jand K can be made from H. Draw skeletal formulae for J and K in the boxes provided. 4 NaBH, H,, Pd catalyst 1] 2] (Total Cp. [Turn over16 8 _Inthis question, one mark is available for the quality of written communication. (_ Ketones of aifarnt chain lengtns are important fo the flavour of dairy foods. You are given a sample of an unknown ketone Isolated from cheese. Describe how you would ‘+ dotect tho presence ot a carbonyl group in your compound, ‘+ confirm that itis a ketone and not an aldehyde, ‘+ use a chemical method to identity which ketone you have, (8) Quality of Written Communication {1] {Total: 9] Copyrht Actnostoderent CQueston a) mime spelt SBS Web Nip ais 9 ARODEVSDBS/14 0002 fw ‘OCR nas mado every eat to baco te copygh Hees ol ame uend mn ue quscon pape, bu we have macvetenlyevedockad Oy, WO apolase ase suo2 Fo Answer all the questions. 1 (a) (i) Name the compound CH,CHO. (W)_ Name the functional group of CH,CHO. (il) Draw structural formulae for the organic producis of the reactions below. NaBH, HCHO) ammoniacal AgN jG ccxo ite (Tollens' reagent) fa Describe what is meant by nucleophilic addition. rot GHaGHO-with-HGNtia the presence af KChin-yeur answer. C) 810 5 Benzene and phenylethene are aromatic hydrocarbons. Phenylethene also has an alkene group in its side chain, and shows reactions typical of both arenes and alkenes. Oo (a) In this question, one mark is available for the quality of written communication. Describe the bonding in benzene. Include in your answer the model used for the arrangement of electrons, 5) ‘Quality of Written Communication [1] (b) Phenylethene, C,H,CH=CH,, reacts readily with bromine in an inert solvent. Benzene reacts with bromine only in the presence of a catalyst. ©) ©) Draw the structural formula of the organic product obtained when phenylethens reacts with bromine in an inert solvent, mn ©) _ (Explain why benzene reacts less readily than phenylethene with bromine. (©). State one major use for phenylethene. (Total: 12] Turn over12 6 Compound Bis a secondary iodoalkane, C,Hol. (2) Deduce the mass:charge ratio (m/e) of the molecular ion in the mass spectrum of B. G]_ ©) When B, C,Hgl i reacted with hot ethanolic sodium hydroxide, HI is eliminated and three isomeric alkenes C, D and E are formed. C, D and E form the same compound, F, when reacted with hydrogen in the presence of a palladium catalyst, () Suggest structural formulae for B, C, D, E and F. Give your reasoning. (8) (il) Classify the type of reaction in which ©, D or E is converted into F using hydrogen and a palladium catalyst. At] Total: 10)