SUMMATIVE ASSESSMENT THIR TERM ST!M "#$% TERENGGANU
SECTION A [ 15 marks ] Four suggested answers labelled A& '& C and are given for each question. Choose one correct answer. $ A compound with the molecular formula CH 3 CHNH ! "C##H e$i%t% in two %hape%& 'hat i% it called( A )%otope%& ' Ci% * tran% i%omer%& C #ptical i%omer%& +tructural i%omer%&
" 'hat rea,ent i% u%ed to differentiate the followin, compound% -elow(
A .romine water ' Car-on dio$ide C Ethano/l chloride 0iluted h/drochloric acid % 'hich reaction %how% the propa,ation %tep durin, the reaction -etween methane and chlorine in the pre%ence of li,ht( A H 1 Cl ! HCl 1 Cl ' CH 2 1 Cl 1 CH 3 Cl 1 H 1 C CH 2 1 Cl 1 CH 3 1 1 HCl CH 2 1 Cl CH 3 1 HCl ! CH ! #H #H
( 'hich car-on atom can mo%t ea%il/ -e attac3ed -/ an electrophile(
A
CH ! .r H 3 C 0
C#CH 3 . C ) 'hich one of the followin,% will -e produced throu,h the reaction -etween phenol and chlorine %olution(
A
'
C
3 #Cl CH 3 #H Cl #H Cl Cl Cl
| | * 'hich compound can chan,e the C = # ,roup in propanone to C Cl
( | |
A Chlorine ,a% ' 4ho%phorou% 5" chloride C +odium chloride 0ilute h/drochloric acid + #ne component of -ee%wa$6 which i% u%ed a% a car poli%h6 ha% the formula CH 3 CH ! " !2 C##CH ! " !7 CH 3 & 'hat are the product% of the acidic h/drol/%i% of thi% component( A CH 3 CH ! " !3 C##H and CH 3 CH ! " !7 C##H . CH 3 CH ! " !2 C##H and CH 3 CH ! " !8 C##H C CH 3 CH ! " !2 C##H and CH 3 CH ! " !7 #H 0 CH 3 CH ! " !2 #H6 CH 3 CH ! "#H and C# ! , 'hen -romine water i% added to phen/lamine6 the -romine water i% decolouri%ed& 'hich %tatement e$plain% the o-%er9ation a-o9e( A 4hen/lamine o$idi%e% .r ! into .r : & ' The NH ! ,roup in phen/lamine i% %u-%tituted with .r ! & C The NH ! ,roup phen/lamine react% with .r ! & .romine %u-%titute% h/dro,en in the -en;ene rin,& 2
- A%partame i% an artificial %weetener which ha% the %tructural formula a% follow%< # # == == H ! N CH C NH CH C #CH 3 . . CH ! CH ! | | C##H
'hich functional ,roup i% no/ found in the a%partame molecule(
A E%ter ' Amino acid C Car-o$/l ,roup Car-on/l ,roup $# The repeatin, unit of a pol/mer i% a% follow%&
'hich of the followin, can produce the a-o9e pol/mer( A ' C 5
$$ 'hat are the %imilaritie% amon, %olid enantiomer% optical i%omer%"(
$ Relati9e molecular ma%% " >eltin, point % Chemical propertie% A $ ' $&" C "&% $&"&% $" 'hat are the compound% produced when -utan:!:ol i% reflu$ed with acidified pota%%ium man,anate5))" %olution( $ .utanone " .utanoic acid % .utanol
A $ ' $&" C "&% $&"&% $% 'hat i% the t/pe of reaction that will occur to the compound -elow( CH 3 C# CH 3
A $ ' $&" C "&% $&"&% $( A part of a pol/mer %tructure i% a% follow%< ANHC#CH ! " 2 C# ! CH ! " ! NHC#CH ! " 2 C# ! CH ! " ! : 'hich %tatement% are true a-out thi% pol/mer( I )t can -e %/nthe%i%ed from C)C#CH ! " 2 C#C1 and H#CH ! CH ! NH ! & " )t i% a pol/amide and al%o a pol/e%ter& % )t i% re%i%tant a,ain%t al3aline h/drol/%i%& A $ ' $&" C "&% $&"&%
$) There are %aturated and un%aturated pol/mer%& 'hich pol/mer%" decolouri%e%" an acidified %olution of pota%%ium man,anate 5))"( $ 4ol/!:meth/l-uta:1 63:diene" " 4ol/ethene"& % 4ol/phen/lethene" A $ ' $&" C "&% $&"&% B
SECTION B [15 marks] Answer all questions in this section. 16 a" 0raw the %tructure of the maCor product of each of the followin, reaction%& 012 :'r 3 NH %
0112 0CH % 2 " C'r " 3 NaOH
01112 4CHO
[3 >ar3%] -" The %tructural formula of an or,anic compound i% a% follow%< H# CH ! CHCH 3
#H 0raw the %tructural formula of the or,anic product%" formed when the compound react% with each of the followin, rea,ent%< i" %odium metal [1 mar3] ii" An aDueou% %olution of %odium h/dro$ide& [1 mar3] iii" An al3aline iodine %olution& [1 mar3] i9" A hot acidic pota%%ium man,anate5))" %olution& [1 mar3] 8 Ethanol i" CH 3 CH ! >,.r ii" H 3 # 1
17 a" Ethene react% with -romine 9ia electrophile addition mechani%m i" 'hat i% meant -/ electrophile( EEEEEEEEEEEEEEEEEEEEEEEEEEE& EEEEEEEEEEEEEEEEEEEEEEEEEEE EEEEEEEEEEEEEEEEEEEEEEEEEEEEEE [1 mar3] ii" 'rite a -alance eDuation for the reaction the reaction ta3in, place& [! mar3%] -" The formulae of pol/mer% F and G are ,i9en -elow& i" 'rite the %tructural formulae of the monomer% of pol/mer% F and G& [3 mar3%]
ii" +tate the t/pe% of pol/rneri%ation in9ol9ed in the formation of pol/mer% F and G&
SECTION C [30 marks] Answer any two questions in this section. $, a" )dentif/ the t/pe of i%omeri%m %hown -/ !:-utanol and -utenedioic acid& E$plain wh/ the%e compound% e$hi-it i%omeri%m& 0raw the pair of i%omer% for each compound& [6 Marks] -" An or,anic compound 4 ha% the molecular formulaC 5 H 1! # 6& 4 to form H ha% a chiral car-on atom and decolouri%e% hot6 acidified pota%%ium man,anate 5))" %olution& .oth 4 and H form% a /ellow precipitate when reacted with an al3aline iodine %olution& H form% a /ellow precipitate with !62:dinitrophen/lh/dra;ine& 0etermine the %tructural formula of 4 and H& E$plain the a-o9e o-%er9ation% and write the appropriate eDuation% for the reaction%& [9 Marks ] $- a" i" 'rite the mechani%m of the reaction when 1:chloropropane i% reflu$ed with aDueou% %odium h/dro$ide& Name the t/pe of reaction in9ol9ed& [3 marks] ii" +tate and e$plain how the rate of thi% reaction chan,e% when 1:chloropropane i% replaced -/ 1:-romopropane& [3 marks] iii" 'rite the eDuation% to %how how /ou would chan,e 1:chloropropane to !:chloropropane& [5 marks] -" Catal/tic crac3in, i% a proce%% where lon, chained al3ane% are -ro3en into mi$ture of %hort chained molecule%&
i" E$plain the importance of the catal/tic crac3in, proce%% in indu%trie%& [! marks] ii" +tate the condition% reDuired for thi% proce%%& [! marks] 1I
"# +u,,e%t how each of the followin, con9er%ion% can -e carried out& )n each ca%e /our an%wer %hould include %ucce%%i9e %tep% of the con9er%ion and al%o rea,ent and condition u%ed in each %tep& a" Ethanol to propanoic acid [4 marks] -" 14propanol to !4propanol [3 marks] c" !4-romopropane to propanone [3 marks] d" 4ropane414ol to !4meth/lpropanoic acid [5 marks] END OF QUESTION PAPER 11
Physical Organic Chemistry—Ii: Specially Invited Lectures Presented at the Second IUPAC Conference on Physical Organic Chemistry Held at Noordwijkerhout, Netherlands, 29 April–2 May 1974