I BChemi mi st r y–SL Topi c10Quest i ons
1.
Which of the structures below is an aldehyde? al dehyde? A. B. C. D. (Total 1 mark)
2.
What product results from the reaction of CH 2==CH2 with Br2? A.
CHBrCHBr
B.
CH2CHBr
C.
CH3CH2Br
D.
CH2BrCH2Br (Total 1 mark)
3.
What is the nal product formed when CH 3CH2!H is re"u#ed with acidied potassium dichromate$%&'? A.
CH3CH!
B.
CH2==CH2
C.
CH3C!!H
D.
HC!!CH3 (Total 1 mark)
4.
Which substance$s' could be formed durin( the incomplete combustion of a hydrocarbon? &.
Carbon
A.
& only
B.
& and && only
C
& )and &&& only
D.
&& and &&& only
&&.
Hydro(en
&&&.
Carbon mono#ide
(Total 1 mark)
5.
Which formulas represent butane or its isomer? &.
CH3$CH2'2CH3
&&.
CH3CH$CH3'CH3
&&&.
$CH3'3CH
A.
& and && only
B.
& and &&& only
C.
&& and &&& only
D.
&* && and &&& (Total 1 mark)
6.
Which statement about nei(hbourin( members of all homolo(ous series is correct? A.
+hey +hey ha,e ha,e the the sam same e emp empir iric ical al for formula mula..
B.
+hey di-er by a CH2 (roup.
C.
+hey +hey poss posses ess s di-e di-ere rent nt func functi tion onal al (rou (roups ps..
D.
+hey +hey di-e di-err in in the their ir de(r de(ree ee of unsa unsatu turat ratio ion. n. (Total 1 mark)
7. What is the &/AC name for CH 3CH2CH$CH3'2? A.
0*01di 1dimeth ethylpropane
B.
21methylbutane
C.
isopentane
D.
ethyldimeth ethylmeth ethane (Total 1 mark)
8.
Which compound has the lowest boilin( point? A.
CH3CH2CH$CH3'CH3
B.
$CH3'C
C.
CH3CH2CH2CH2CH3
D.
CH3CH2!CH2CH3 (Total 1 mark)
9.
What type of reaction does the euation below represent?
&&.
CH3CH$CH3'CH3
&&&.
$CH3'3CH
A.
& and && only
B.
& and &&& only
C.
&& and &&& only
D.
&* && and &&& (Total 1 mark)
6.
Which statement about nei(hbourin( members of all homolo(ous series is correct? A.
+hey +hey ha,e ha,e the the sam same e emp empir iric ical al for formula mula..
B.
+hey di-er by a CH2 (roup.
C.
+hey +hey poss posses ess s di-e di-ere rent nt func functi tion onal al (rou (roups ps..
D.
+hey +hey di-e di-err in in the their ir de(r de(ree ee of unsa unsatu turat ratio ion. n. (Total 1 mark)
7. What is the &/AC name for CH 3CH2CH$CH3'2? A.
0*01di 1dimeth ethylpropane
B.
21methylbutane
C.
isopentane
D.
ethyldimeth ethylmeth ethane (Total 1 mark)
8.
Which compound has the lowest boilin( point? A.
CH3CH2CH$CH3'CH3
B.
$CH3'C
C.
CH3CH2CH2CH2CH3
D.
CH3CH2!CH2CH3 (Total 1 mark)
9.
What type of reaction does the euation below represent?
CH2=CH2 4 Br2 5 BrCH2CH2Br A.
substitution
B.
condensation
C.
reduction
D.
addition (Total 1 mark)
10. Which compound is a member of the same homolo(ous series as 01 chloropropane? A.
01chloropropene
B.
01chlorobutane
C.
01bromopropane
D.
0*01di 1dichloro oropro propane (Total 1 mark)
11. Which formula is a correct representation of pentane? A.
CH3CH2CHCH2CH3
B.
$CH3CH2'2CH3
C.
CH3$CH2'3CH3
D.
CH3$CH3'3CH3 (Total 1 mark)
12. How many structural isomers are possible with the molecular formula C 6 H0? A.
B.
7
C.
6
D.
8 (Total 1 mark)
13. Which compound is a member of the aldehyde homolo(ous series? A.
CH3C!CH3
B.
CH3CH2CH2!H
C.
CH3CH2C!!H
D.
CH3CH2CH! (Total 1 mark)
14. Which type of compound can be made in one step from a secondary alcohol? A.
an aldehyde
B.
an al9ane
C.
a carbo#ylic acid
D.
a 9etone (Total 1 mark)
15. Which formula represents a tertiary alcohol? (Total 1 mark)
16. Which reaction type is typical for halo(enoal9anes? A.
nucleophilic substitution
B.
electrophilic substitution
C.
electrophilic addition
D.
nucleophilic addition (Total 1 mark)
17. Which substance is not readily o#idi:ed by acidied potassium dichromate$%&' solution? A.
propan101ol
B.
propan121ol
C.
propanal
D.
propanone (Total 1 mark)
18. What is the correct name of this compound?
A.
0*31dimethylbutane
B.
2*1dimethylbutane
C.
21methylbutane
D.
21methylpentane (Total 1 mark)
19. /ropane* C3H;* under(oes incomplete combustion in a limited amount of air. Which products are most li9ely to be formed durin( this reaction? A.
Carbon mono#ide and water
B.
Carbon mono#ide and hydro(en
C.
Carbon dio#ide and hydro(en
D.
Carbon dio#ide and water (Total 1 mark)
20. What is
CH3CH2Br
B.
CH3CH2Br and H2
C.
CH2BrCH2Br
D.
CH3BrCH2 Br and H 2 (Total 1 mark)
21. Which are characteristics typical of a free radical? &. &&. &&&.
&t has a lone pair of electrons. &t can be formed by the homolytic ssion of a co,alent bond. &t is unchar(ed.
A.
& and && only
B.
& and &&& only
C.
&& and &&& only
D.
&* && and &&& (Total 1 mark)
22. Which of the followin( products could be formed from the o#idation of ethanol? &.
ethanal
&&.
ethanoic acid
&&&.
ethane
A.
& and && only
B.
& and &&& only
C.
&& and &&& only
D.
&* && and &&& (Total 1 mark)
23. What is the reaction type when $CH 3'3CBr reacts with aueous sodium hydro#ide to form $CH3'3C!H and aBr? A.
Addition
B.
>limination
C.
0
D.
2 (Total 1 mark)
24. Which species is a free radical? A.
@CH3
B.
4
C.
D.
CH3
CH3
CH3
(Total 1 mark)
25. Which compound is a tertiary halo(enoal9ane? A.
$CH3CH2'2CHBr
B.
CH3$CH2'3CH2Br
C.
$CH3'2CHCH2CH2Br
D.
CH3CH2C$CH3'2Br (Total 1 mark)
26. Which species reacts most readily with propane? A.
Br2
B.
Br@
C.
Br
D.
Br
4
(Total 1 mark)
27. An or(anic compound X reacts with e#cess acidied potassium dichromate$%&' to form compound Y * which reacts with sodium carbonate to produce C!2$('. What is a possible formula for compound X? A.
CH3CH2C!!H
B.
CH3CH2CH2!H
C.
CH3CH$!H'CH3
D.
$CH3'3C!H (Total 1 mark)
28. Which statement about successi,e members of all homolo(ous series is correct? A.
+hey ha,e the same empirical formula.
B.
+hey di-er by a CH2 (roup.
C.
+hey ha,e the same physical properties.
D.
+hey di-er in their de(ree of unsaturation. (Total 1 mark)
29. +he followin( is a three1dimensional representation of an or(anic molecule.
Which statement is correct? A.
+he correct &/AC name of the molecule is 21methylpentane.
B.
All the bond an(les will be appro#imately E.
C.
!ne isomer of this molecule is pentane.
D.
+he boilin( point of this compound would be hi(her than that of pentane. (Total 1 mark)
30. Which compound forms when hydro(en bromide is added to but121ene? A.
21bromobutane
B.
2*31dibromobutane
C.
01bromobutane
D.
0*21dibromobutane (Total 1 mark)
31. Which products can be potentially obtained from crude oil and are economically important? &.
/lastics&&.
A.
& and && only
B.
& and &&& only
C.
&& and &&& only
D.
&* && and &&&
Far(arine&&&. Fotor fuel
(Total 1 mark)
32. /ropane* C3H;* under(oes incomplete combustion in a limited amount of air. Which products are most li9ely to be formed durin( this reaction? A.
Carbon mono#ide and water
B.
Carbon mono#ide and hydro(en
C.
Carbon dio#ide and hydro(en
D.
Carbon dio#ide and water (Total 1 mark)
33. +wo reactions of an al9ene* B* are shown below.
$i'
tate the name of A and write an euation for its complete combustion. >#plain why the incomplete combustion of A is dan(erous. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. (5)
$ii'
!utline a test to distin(uish between A and B* statin( the result in each case. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG..
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. (3)
$iii' Write an euation for the con,ersion of B to C. tate the type of reaction ta9in( place and draw the structure of C. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. (3) (Total 11 marks)
34. or the two compounds HC!!CH 2CH3 and HC!!CHCH 2 & && $i'
tate and e#plain which of the two compounds can react readily with bromine. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG.. (2)
$ii'
Compound && can form polymers. tate the type of polymeri:ation compound && under(oes* and draw the structure of the repeatin( unit of the polymer. (2) (Total 4 marks)
35. +he compound C2H can be used as a startin( material for the preparation of many substances. $a'
ame the compound C2H and draw its structural formula. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (2)
$b'
&n the scheme below* state the type of reaction and identify the rea(ent needed for each reaction.
ABC2H 5 CH3CH2!H 5 CH3C!!H GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (4)
$c'
C2H can be con,erted into one of the compounds below in a sin(le step reaction. C2H3Cl
C2HCl2
Draw the structural formula for each of these compounds and identify the compound which can be formed directly from C2H. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (3)
$d'
!ne of the two compounds in $c' has an isomer. Draw the structural formula of the isomer and e#plain why it can not be formed directly from C2H. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (2)
$e'
C2H can also react to form a polymer. ame this typ of polymer and draw the structural formula of a section of this polymer consistin( of three repeatin( units.
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (2)
$f'
/olymers can also be formed in a di-erent type of reaction. &dentify this type of reaction and name t!o di-erent types of such polymers. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (3) (Total 16 marks)
36. +he plastic /%C* poly$chloroethene'* is made from the monomer chloroethene* C2H3Cl* by a polymeri:ation reaction. $i'
Draw the structural formula of chloroethene. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (1)
$ii'
tate the type of polymeri:ation reaction that occurs to ma9e poly$chloroethene' and identify the structural feature needed in the monomer. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (2)
$iii' Draw the structure of the repeatin( unit of poly$chloroethene'. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG
(1)
$i,' >#plain why monomers are often (ases or ,olatile liuids* whereas polymers are solids. GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGG (2) (Total 6 marks) 3
37. +he hydrolysis of 21iodo121methylpropane by .0 mol dm I!H$a' to form 21methylpropan121ol is an e#ample of nucleophilic substitution. Ji,e euations to illustrate the S0 mechanism for this reaction. ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... (Total 2 marks)
38. +he molecular formula CHBr represents four structural isomers* all of which can under(o nucleophilic substitution reactions with aueous sodium hydro#ide. An euation to represent all these reactions is CHBr 4 a!H $a'
→CH!H
4 aBr
>#plain what is meant by the term nucleophilic substitution. (2)
$b'
+he main mechanism for a tertiary halo(enoal9ane is 0. Ji,e the euations for this substitution reaction of the tertiary isomer of C HBr. how the structures of the or(anic reactant and product and use curly arrows to show the mo,ement of electron pairs. (4)
$c'
+he main mechanism for a primary halo(enoal9ane is 2. Ji,e the mechanistic euation for this substitution reaction of the strai(ht1chain primary isomer of CHBr* showin( the structures of the or(anic reactant and product* and usin( curly arrows to show the mo,ement of electron pairs. (4)
$d'
Ji,e a structural formula for the secondary isomer and for the other primary isomer. tate the name of each isomer.
(4) (Total 14 marks)
39. Write euations to show the mechanisms of the followin( reactions. &n each case* show the structure of the intermediate and or(anic product* and use curly arrows to show the mo,ement of electron pairs. $i'
the reaction between I!H and CH3CH2CH2CH2Cl.
(3)
$ii'
the reaction between I!H and $CH3'3CCl.
(2) (Total 5 marks)
40. ome alcohols are o#idi:ed by heatin( with acidied potassium dichromate$%&'. &f o#idation does occur* identify the possible o#idation products formed by each of the alcohols below. &ndicate if no o#idation occurs. Butan101ol ......................................................................................................................... ..................... ......................................................................................................................... ..................... Butan121ol ......................................................................................................................... ..................... ......................................................................................................................... ..................... 21methylpropan121ol ......................................................................................................................... ..................... ......................................................................................................................... ..................... (Total 4 marks)
41. Chlorine and ethane react to(ether to form chloroethane. $a'
tate the condition needed for the reaction to occur. ................................................................................................................. ................... ................................................................................................................. ................... (1)
$b'
Write euations to represent initiation* propa(ation and termination steps in the reaction. ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... (4) (Total 5 marks)
42. CH3C!CH3 is the rst member of the 9etone homolo(ous series. Draw the full structural formula of the ne#t member of this homolo(ous series and predict how its meltin( point compares with that of CH3C!CH3. (Total 2 marks)
43. $i'
Write an euation for the reaction between but121ene and bromine* showin( the structure of the or(anic product. ................................................................................................................. .................. .................................................................................................................
.................. ................................................................................................................. .................. ................................................................................................................. .................. (2)
$ii'
tate the type of reaction occurrin(. ......................................................................................................... ................ ......................................................................................................... ................ (1) (Total 3 marks)
44. CH3C!CH3 can be prepared in the laboratory from an alcohol. tate the name of this alcohol* the type of reaction occurrin( and the rea(ents and conditions needed for the reaction. (Total 5 marks)
45. 21bromobutane can be con,erted into butan121ol by a nucleophilic substitution reaction. +his reaction occurs by two di-erent mechanisms. $i'
Ji,e the structure of the transition state formed in the S2 mechanism. (2)
$ii'
Write euations for the S0 mechanism. (2) (Total 4 marks)
46. >thene is an unsaturated hydrocarbon used as a startin( materi al for many or(anic chemicals. $a'
Draw the structural formula of ethene and state the meanin( of the term unsaturated hydrocarbon. (2)
$b'
tate an euation for the con,ersion of ethene to ethanol and identify the type of reaction. (2)
$c'
Describe the complete o#idation of ethanol and name the product. &nclude the conditions* rea(ents reuired and any colour chan(es. (4)
$d'
tate an euation for the reaction between ethanol and the product of complete o#idation in $c'. &nclude any other rea(ent reuired for this reaction. ame the or(anic product and state on possible use of this product. (4) (Total 12 marks)
47. >thene is an unsaturated hydrocarbon used as a startin( materi al for many or(anic chemicals. $a'
tate the meanin( of the term unsaturated hydrocarbon. (1)
$b'
tate an euation for the con,ersion of ethene to ethanol and identify the type of reaction. (2)
$c'
Describe the complete o#idation of ethanol. &nclude the conditions* rea(ents reuired and any colour chan(es. ame the or(anic product X. (4)
$d'
tate an euation for the reaction between ethanol and compound X. &nclude any other rea(ent reuired. ame the or(anic compound " and state on use of this product. (4) (Total 11 marks)
48. +he euation for a reaction of ethane is CH3CH3 4 Cl2
→CH3CH2Cl
4 HCl
+he mechanism of this reaction in,ol,es initiation* propa(ation and termination steps. Describe this reaction* includin( euations for each step and the role of ultra,iolet li(ht. ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... .........................................................................................................................
..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... ......................................................................................................................... ..................... (Total 5 marks)
49. $i'
Draw the structural formula of propan121ol.
(1)
$ii'
&dentify the alcohol as primary* secondary* or tertiary. ................................................................................................................. ................... (1)
$iii' &dentify the or(anic product formed by the o#idation of this alcohol usin( acidied potassium dichromate$%&' solution. ......................................................................................................... ................. (1) (Total 3 marks)
50. econdary halo(enoal9anes can under(o nucleophilic substitution reactions by both 0 and 2 mechanisms. +he mechanism showin( the formation of the transition state in the reaction between 21bromobutane and potassium hydro#ide can be represented as follows.
$a'
&dentify the type of mechanism shown. ................................................................................................................. ................... (1)
$b'
tate and e#plain how the followin( chan(es would alter the rate of the reaction by this mechanism. $i'
usin( water instead of potassium hydro#ide. ......................................................................................................... ................. ......................................................................................................... ................. ......................................................................................................... ................. ......................................................................................................... ................. (2)
$ii'
usin( bromoethane instead of 21bromobuture. ......................................................................................................... ................. ......................................................................................................... ................. ......................................................................................................... ................. ......................................................................................................... ................. (2) (Total 5 marks)
51. +he followin( is a computer1(enerated representation of the molecule* methyl 21hydro#y ben:oate* better 9nown as oil of winter(reen.
$i'
Deduce the empirical formula of methyl 21hydro#y ben:oate and draw the full structural formula* includin( any multiple bonds that may be present.+he computer1(enerated representation shown does not
distin(uish between sin(le and multiple bonds. (2)
$ii'
&n this representation* two of the carbon1o#y(en bond len(ths shown are .02 nm and .0383 nm. >#plain why these are di-erent and predict the carbon1o#y(en bond len(th in carbon dio#ide. (2)
$iii' ame all the functional (roups present in the molecule. (2) (Total 6 marks)
52. $i'
tate and e#plain the trend in the boilin( points of the rst si# al9anes in,ol,in( strai(ht1chains. (2)
$ii'
Write an euation for the reaction between methane and chlorine to form chloromethane. >#plain this reaction in terms of a free1radical mechanism. (5) (Total 7 marks)
53. $i'
&dentify the formulas of the or(anic products* A>* formed in the reactions* ##$
#.
CH3$CH2';!H 4 I 2Cr2!8
##.
$CH3'3CBr 4 a!H C
###.
$CH3'2CH!H 4 I 2Cr2!8 %
#$.
H2C=CH2 4 Br2 & (5)
$ii'
H2C=CH2 can react to form a polymer. ame this typ of polymer and draw the structural formula of a section of this polymer consistin( of three repeatin( units. (2) (Total 7 marks)
54. >thene* propene and but121ene are members of the al9ene homolo(ous series. $a'
Describe t'r features of members of a homolo(ous series. (3)
$b'
tate and e#plain which compound has the hi(hest boilin( point. (3)
$c'
Draw the structural formula and (i,e the name of an al9ene containin( ,e carbon atoms. (2)
$d'
Write an euation for the reaction between but121ene and hydro(en bromide* showin( the structure of the or(anic product. tate the type of reaction occurrin(. (3)
$e'
/ropene can be con,erted to propanoic acid in three steps step0 step 2 step 3 propene propan101ol propanal propanoic acid tate the type of reaction occurrin( in steps 2 and 3 and the rea(ents needed. Describe how the conditions of the reaction can be altered to obtain the ma#imum amount of propanal* and in a separate e#periment* to obtain the ma#imum amount of propanoic acid. (5)
$f'
&dentify the stron(est type of intermolecular force present in each of the compounds propan101ol* propanal and propanoic acid. Kist these compounds in decreasin( order of boilin( point. (4) (Total 20 marks)
55. $a'
tate t!o characteristics of a homolo(ous series. ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... (2)
$b'
Describe a chemical test to distin(uish between al9anes and al9enes* (i,in( the result in each case. ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... (3) (Total 5 marks)
56. +he followin( transition state is formed durin( the reaction of a halo(enoal9ane with aueous sodium hydro#ide
$a'
Deduce the structure of the halo(enoal9ane. Classify it as primary* secondary or tertiary* (i,in( a reason for your choice. ................................................................................................................. ................... ................................................................................................................. ................... (2)
$b'
+he mechanism of this reaction is described as 2. >#plain what is meant by the symbols in 2. /redict a rate e#pression for this reaction. ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... (3)
$c'
+he same halo(enoal9ane reacts with sodium hydro#ide by an 0 mechanism. Deduce the structure of the intermediate formed in this reaction. ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... ................................................................................................................. ................... (1) (Total 6 marks)
57. $a'
Kist t!o characteristics of a homolo(ous series. ................................................................................................................. .................... ................................................................................................................. .................... ................................................................................................................. .................... (1)
$b'
>thanol and ethanoic acid can be distin(uished by their meltin( points. tate and e#plain which of the two compounds will ha,e a hi(her meltin( point.
................................................................................................................. .................... ................................................................................................................. .................... ................................................................................................................. .................... ................................................................................................................. .................... (2)
$c'
Draw the t'r isomers containin( the alcohol functional (roup of formula CH!H.
(2) (Total 5 marks)
I BChemi st r y–SL Topi c10Answer s
1.
A 1
2.
D 1
3.
C 1
4.
C 1
5.
D 1
6.
B 1
7.
B 1
8.
B 1
9.
D 1
10. B 1
11. C 1
12. B 1
13. D 1
14. D 1
15. C 1
16. A 1
17. D 1
18. D 1
19. A 1
20. A 1
21. C 1
22. A 1
23. C 1
24. A 1
25. D 1
26. B 1
27. B 1
28. B 1
29. C 1
30. A 1
31. B 1
32. A 1
33. $i'
butaneLCH0$(' 4 !2$(' → C!2$(' 4 7H2!$l'L(ignore state symbols, accept balancing using 13O 2 ) [1] for all formulas and [1] for balancing equation.C! producedLC! is poisonous
orCLwhich causes respiratory problemsL $ii'
7
add Br2 $water'L"alid test needed to score further mar#s. A no e-ectLB would decolorise Br 2 $do not accept discolour 'L
$iii' CH3CH==CHCH3 4 HBr → CH3CHBrCH2CH3L [1] for $%r in balanced equation, [1] for structure of product.
3 3
additionL 11
34. $i'
&& reacts with Br2&& is an al9ene
$ii'
addition polymeri:ationL 2 4
35. $a'
$b'
etheneL
2
A addition
$c' L he compound formed directly may be circled or indicated by some 3 other means. &ccept any other structure sho+ing a l atom on each atom. $d' L addition across a double bond occurs at both C atoms -OW!L f 1,1/dichloroethane is gi"en in (c) accept 1,2/ dichloroethane as the isomer as !0 but &+ard [1] ma
2
$e'
addition polymerL
2
$f'
condensation polymerL polyestersL polyamidesL
3 16
36. $i' $ii'
CH2CHCl
0
addition $polymeri:ation'L $carbon1carbon' double bond
2
$iii' ;
1
$i,' monomers ha,e smaller molecules
2 6
37. $CH3'3C& 4
→$CH3'3C −
$CH3'C 4 !H
4
−
4 & L
→$CH3'3C!HL
2
o not allo+ S4 2 reaction. 2
38. $a'
replacement of atom<(roup $in a molecule'
electron1decient carbon atomL $b'
2
correct structure of $CH3'3CBrL curly arrow showin( C⎯Br bond ssionL 4
correct structure of $CH 3'3C L −
curly arrow showin( attac9 by !H on correct C atomL correct structure of $CH 3'3C!HL &+ard [1] each for any four. $c'
correct structure of CH3CH2CH2CH2BrL curly arrow showin( C⎯Br bond ssionL correct structure of transition state showin( char(e and all bondsL −
curly arrow showin( attac9 by !H on correct C atomL correct structure of CH 3CH2CH2CH2!HL &+ard [1] each for any four. $d'
secondary CH3CHBrCH2CH3L 21bromobutaneL other primary $CH3'2CHCH2BrL 01bromo121methylpropaneL
14
39. $i'
$2 mechanism'
3
ntermediate structure sho+ing o"erall negati"e charge and partial bonds. &ccept negati"e charge to be indicated as delocalised bet+een the $O/$2/l. →H! − CH2CH2CH2CH3 4
$ii'
−
Cl L
$0 mechanism'
2
5
40. butan101ol butan121ol
butanalL butanoic acidL butanoneL
2 methylpropan121ol o#idationL &lso accept correct structures. Where both name and structure gi"en structure must be correct and name largely correct.
no
4
41. $a'
% li(ht
0
$b'
+hrou(hout accept radical with or without @ initiation reaction(s)5 Cl2
→2Cl@L
0
propagation reactions5 Cl@ 4 CH3CH3 →CH3CH2@ 4 HClL CH3CH2@ 4 Cl2 →CH3CH2Cl 4 Cl@L
2
termination reactions5 CH3CH2@ 4 Cl@ →CH3CH2ClL 2Cl@ →Cl2L 2CH3CH2@ →CH3CH2CH2CH3L &+ard [1] for any termination reaction. f initiation, propagation, termination not labelled or incorrectly labelled a+ard [3] ma.
0
5
42. 2
43. $i'
$ii'
CH; 4 Br2 →CH;Br2L !quation scores [1]. CH3CHBrCHBrCH3L &ccept more detailed formula.
2
additionL
0 3
44. propan121olL &ccept 2/propanol. o#idation
45. $i'
all ,e (roups around C correctL ne(ati,e char(e and dotted lines to !H and Br correctL nd o not a+ard 2 mar# if bond from O$ (i.e. O$/////). $ii'
CH3CH2CH$CH3'Br 4
→CH3CH2CH$CH3'
CH3CH2CH$CH3' 4 !H
−
4
2
−
4 Br L
→CH3CH2CH$CH3'!HL
2
&ccept *$8 instead of $ 3$2$($3 ) throughout. 4
46. $a'
&llo+ $29$2. a hydrocarbon that contains at least one C=C $or C ≡C'
$c'
C2H 4 H2! →C2H7!HL addition
2
heat under re"u#L >&+H>M potassium dichromate$%&'
4
!M potassium perman(anate
ethanoic acidL
$d'
CH3C!!H 4 C2H7!H →CH3C!!CH2CH3 4 H2!L &ccept $3OO2$> sulfuric acid
12
47. $a'
$b'
$c'
a hydrocarbon that contains at least one C=C $or C≡C'
2
heat under re"u#L >&+H>M 2
4
potassium dichromate$%&'
!M
potassium perman(anate
acidied
CH3C!!H 4 C2H7!H CH3C!!CH2CH3 4 H2!L ?
accept equations including $ . @e"ersible arro+ not required for the mar#. sulfuric acid
11
48. ultra,iolet li(ht causes Cl −Cl bond to splitL Cl2 →2Cl@L Cl@ 4 CH3CH3 →CH3CH2@ 4 HClL CH3CH2@ 4 Cl2 →CH3CH2Cl 4 Cl@ CH3CH2@ 4 Cl@ →CH3CH2Cl
7
f diAerent al#ane used, then deduct [1]. 4o penalty for not labelling steps, but deduct [1] if any +rongly labelled. 5
49. $i'
0 &llo+ bond to $O rather than O$ or half+ay bet+een the t+o $ii'
secondaryL
$iii' CH3C!CH3
0 0 3
50. $a' $b'
2 < bimolecularL $i'
0
reaction slowerL neutral
$ii'
reaction fasterL less bul9y (roup
2 5
51. $i'
$ii'
$>mpirical formula =' C;H;!3L &llo+ double bonds on arene in alternate positions, or allo+ delocali=ed representation (of pi electrons).
2
the bond at .0383 nm is a double bond an* the bond at .02 nm is asin(le bondLin C!2$(' both bonds are double bonds an* would ha,e a ,aluearound .038 nmL 2
$iii' >sterLArene
2
6
52. $i'
$ii'
boilin( point increases as the number of carbons increases
53. $i'
$ii'
A. = CH3$CH2'8CH!LB. = CH3$CH2'8C!!H. = BrCH2CH2BrL &llo+ correct structural formulas.
7
additionL<1$CH21CH2'31<1$CH2'61L
2 7
54. $a'
$b'
same (eneral formula
3
lar(est $molecular' mass
CH2CHCH2CH2CH3
$d'
$e'
$f'
3
2
CH; 4 HBr →CH3CH2CHBrCH3L &+ard [1] for all molecular formulas correct and [1] for correct product structure. &+ard [1] for completely correct equation starting +ithbut/1/ene. additionL
3
o#idation
7
$propan101ol' hydro(en bondin(L $propanal' dipole1dipole attractionsL $propanoic acid' hydro(en bondin(L propanoic acid O propan101ol O propanalL
20
55. $a'
$b'
same (eneral formulaL successi,e members di-er by CH 2L o not allo+ elements or 6ust :they;. similar chemical propertiesL &llo+ same-constant. (radual chan(e in physical propertiesL o not allo+ change periodically. same functional (roupL &+ard [1] each for any t+o.
2
add bromine $water'L al9anes − no chan(e
3 5
56. $a'
$CH3'2CHBr
