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CIE Nov 2015 v2 Paper 2 Q4
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![Halogenoalkanes are useful intermediates in the synthesis of a wide variety of compounds. PMT (a) 2-bromobutane reacts in two different ways with sodium hydroxide depending on the conditions. When warmed with aqueous sodium hydroxide, 2-bromobutane produces an alcohol that exists as a pair of optical isomers. (i) Give the name of the mechanism of the reaction between 2-bromobutane and aqueous sodium hydroxide.[1] (ii) Explain why the alcohol produced exists as a pair of optical isomers.[1] (iii) Draw the three-dimensional structure of the two optical isomers of the alcohol produced in (ii). Heating 2-bromobutane with ethanolic sodium hydroxide produces a mixture of three alkenes, two of which are a pair of geometrical isomers. (iv) Give the name of the mechanism of the reaction between 2-bromobutane and ethanolic sodium hydroxide.[1] [2]UCLES 2015 9701/22/O/N/15<br />
(v) Draw and name the structures of the pair of geometrical isomers formed by reaction of 2-bromobutane with ethanolic sodium hydroxide. PMT namename[2] (vi) Name the third alkene produced by reaction of 2-bromobutane with ethanolic sodium hydroxide and explain why it does not show geometrical isomerism.[2]UCLES 2015 9701/22/O/N/15 [Turn over<br />
PMT (b) Some reactions involving 2-bromopropane are shown. 10 CH3CHBrCH3 2-bromopropane reaction 6 HBr reaction 1 CH3CH(NH2)CH3 reaction 2 reaction 3 hydrolysis reaction 5 CH3CH2CH2OH reaction 4 CH3CH2CO2H (and CH3CH(NH2)CH3 which is removed) (i) State the reagent needed for reaction 1.[1] (ii) State the reagent needed for reaction 2.[1] (iii) Give the structural formula of X. [1] (iv) Name the type of reaction involved in reaction 4 and suggest a suitable reagent.[2] (v) State the name of a solid catalyst for reaction 5.[1]UCLES 2015 9701/22/O/N/15<br />
11 (vi) Complete the mechanism for the production of 2-bromopropane from Y in reaction 6 shown below. Include the structure of Y and any necessary lone pairs, curly arrows, charges and partial charges. PMT intermediate Br H3C Br CH3 [4] (vii) Give the name of the mechanism in (vi).[1] (viii) 1-bromopropane is a minor product of reaction 6. Explain why 2-bromopropane is the major product of reaction 6.[2] [Total: 22]UCLES 2015 9701/22/O/N/15 [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/November_2015_v2_QP_-_Paper_2_CIE_Chemistry_A-level_4-0.jpg)
![age e 5 Ca amb brid dge Mar rk S Sche eme Inte erna atio nal AS/ /A L Leve elOc ctob ber/N Nov vem PMT PPap per Sy yllab bus 9 970 22 Ma ark To otal ber r 201 15 ark k Sc hem me 2O3 3 + 6 6HC Cl2A AlCl l 3 + 3 3H2 O O OR 2O3 3 + 6 6H 3 3+2 2Al 3H2 2O 2O3 3 + 2N 2O3 3 + 2N aOH H + + 7H H2O aOH H + + 3H H2O 2N NaA l (O OH)4 (H2O O)2 OR 2N NaA l (O OH)4 OR 2O3 3 + 2N aOH H2N NaA AlO2 2 + H H2O OR 2O3 3 + 2O OH 2O3 3 + 2O OH + 7 7H2O O2 2[Al( (OH H2O) H)4(H )2] + 3 3H2O O2 2[Al( (OH H)4] OROR 2O3 3 + 2O OH2 2AlO O2 + H H2O su ulfur fo orms s SO O2 / S SO2 + / m mixe es H H2O H2S SO3 or in n wo ords SO O2 + mixes s H2 2O ( (a acid) ) / o r in wor rds + / m + / m SO O2 + mixes s H2 2O + + (1/ /2O 2)H2 SO4 r in w wor rds / or ucle eoph hilic Su bstit tutio on Ha as a a ch hiral cen rbon n OR R ha as a a ca arbo C att tach hed to 4 4 diff fere ent g grou ntre / / car n / C ups / / ato oms / / cha ains e / lin ha as n no p lane ne o of sy ymm metry El limin natio onCa ambr ridge e Int terna ation nal E Exam mina ation ns 20 015 Q Ques stio on (ii ii) (c c) (a a) ( (i) (i ii) (ii ii) (iv v) [1 1] [1 1] [1 1] [1 1] [2 2] [2 2] [1 4] [1 1] [1 1] [1 1] [1 1] [1+ +1] [2 2] [1 1] [1 1]<br />
age e 6 Ca amb brid dge Mar rk S Sche eme Inte erna atio nal AS/ /A L Leve elOc ctob ber/N Nov vem Q Ques stio on ark k Sc hem me (v v) (v vi) Bu ut-1 -en Hs on o one of t the dou uble- -bon nded d Cs do oes not hav ve 2 2 diff fere ent g grou ups o on b both h ato oms ach atom m in n C= =C s / ea (b b) ( (i) (i ii) (ii ii) (iv v) (v v) am mmo onia a / N H3 pr ropa anoy yl ch hlori H5C OC ide / / C2H H3C CH(N NHC COC C2H5 5)CH H3 Re edu uctio on / lit Li AlH H4 thiu m a alum miniu um h hydr hium m tet trah hydr idoa alum mina ate ride / lith al umi inium m ox xide PMT PPap per Sy yllab bus ber r 20115 9 970 22 (1) Ma ark To otal [1 1] [1 1] [1 1] [1 1] [2 2] [2 2] [1 1] [1 1] [1 1] [1 1] [1 1] [1 1] [1 1] [1 1] [2 2] [1 1] [1 1]Ca ambr ridge e Int terna ation nal E Exam mina ation ns 20 015<br />
age e 7 Ca amb brid dge Mar rk S Sche eme Inte erna atio nal AS/ /A L Leve elOc ctob ber/N Nov vem Q Ques stio on (v vi) (vi ii) (vii ii) ark k Sc hem me 1 = cor rrect t str ructu ure of Y Y an nd cu urly arro ow f from m do oubl e bo ond to H 2 = dip ole and d cu rly a arro w fr rom H-B Br b ond d to Br cor rrect t int erm media ate 3 = 4 = Brwit th lo one pair r an d cu urly arro ow f from m lon ne p pair to C C(+) el ectr roph hilic add ditio se econ ndar ry c arbo ocat tion du ue to o el ectr ron mo ore s stab ble t han prim mar ry er / ( rele easin ng c char racte (pos sitive e) in nduc ctive e eff fect of a alky yl gro oup PMT PPap per Sy yllab bus ber r 20115 9 970 22 Ma ark To otal [1 1] [1 1] [1 1] [1 1] [4 4] [1 1] [1 1] [1 1] [1 1] [2 2] [2 22]Ca ambr ridge e Int terna ation nal E Exam mina ation ns 20 015<br />](https://learnah.org/wp-content/uploads/2018/08/November_2015_v2_MS_-_Paper_2_CIE_Chemistry_A-level_4-0.jpg)
