Transcript
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1. A student reacted 8.72 g of bromobutane with an excess of OH
. The student produced4.28 g of butan--o!.
"n this reaction the h#droxide ion acts as a nuc!eophi!e.
$i% &hat name is gi'en to this t#pe of reaction(
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$ii% +xp!ain the term nucleophile.
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$iii% Out!ine the mechanism for this reaction.
,how cur!# arrows and re!e'ant dipo!es.
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2. +thano!/ 02H1OH/ is manufactured on a !arge sca!e for a wide range of uses such as
a!coho!ic drins/ as an industria! so!'ent and as a raw materia! for the s#nthesis ofman# organic compounds.
+thano!/ 02H1OH/ is manufactured on a !arge sca!e b# two methods
3 ermentation/ using #east/ of sugars/ such as g!ucose/ 0H2O.
0H2O$a5% 202H1OH$a5% 6 20O2$g%
The ethano! is then disti!!ed off.
3 H#dration of ethene/ 02H4/ with steam in the presence of an acid cata!#st.
02H4$g% 6 H2O$g% 02H1OH$g%
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0ompare the sustainabi!it# of these methods of manufacturing ethano! in terms of
3 a'ai!abi!it# of starting materia!s and energ# re5uirements
3 atom econom#.
"n #our answer/ #ou shou!d mae c!ear how the atom econom# of the processes !inswith chemica! theor#.
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3. "n the !aborator#/ ethano! can be oxidised with acidified potassium dichromate$"%.
$a% The ethano! can be oxidised to form either ethana!/ 0H90HO $Fig. 1%/ or
ethanoic acid/ 0H90OOH $Fig. 2%.
1 1 0
1 0 0
9 0
8 0
7 0
6 0
5 0
4 0
3 0
2 0
1 0
0
1 0
e t h a n o !a n d a c i d i f i e dp o t a s s i u md i c h r o m a t e $ " %
w a t e r b a t ha t : ; 0
w a t e r i n
w a t e r o u t
d i s t i ! ! a t e
i c e - w a t e r m i x t u r e
h e a t
w a t e r i n
e t h a n o !a n d a c i d i f i e dp o t a s s i u md i c h r o m a t e $ " %
w a t e r o u t
Fig. 1 Fig. 2
The boi!ing points of ethano!/ ethana! and ethanoic acid are gi'en in the tab!ebe!ow.
0H90H2OH 0H90HO 0H90OOH
boiling point / C 8 2 8
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$ii% wh# the organic product is !ie!# to be ethanoic acid if the apparatus shownin Fig. 2 is used.
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$b% &rite a ba!anced e5uation for the oxidation of ethano! to ethanoic acid.
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5. $a% =ropan-2-o! can be formed b# the h#dration of an a!ene in the presence of acata!#st.
$i% ,uggest a suitab!e cata!#st for this reaction.
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$ii% This is an e!ectrophi!ic addition reaction. &hat is meant b# the termelectrophile(
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$b% A mechanism for the reaction in $a% is shown be!ow.
0 H 9
H 0 H00 0
H
6
6
0 H 9
H 0 H0
H
H
O
H H
H Hs t e p 2s t e p 1 s t e p 3
0 H H90 H 9
H 0 H 6 6
6
H
H
0
H
H
O
H
$i% Add >cur!# arrows? to the mechanism to show the mo'ement of e!ectronpairs in steps 1/ 2and 3.
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$ii% ,uggest/ with a reason/ the ro!e of the H6.
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6. =ropan-2-o! is f!ammab!e and readi!# burns.
&rite a ba!anced e5uation for the comp!ete combustion of propan-2-o!.
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7. our possib!e structura! isomers of 04H:O are a!coho!s. Two are shown be!ow.
H H H H
H H H H
H 0 0 0 0 O H
H H O H H
H
HHHH
H 0 0 0 0
butan--o! butan-2-o!
$i% @raw the other two structura! isomers of 04H:O that are a!coho!s
isomer isomer 2
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$ii% ame isomer . ...............................................................................................
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8. Butan-2-o! can be deh#drated to produce a mixture of three a!enes each with amo!ecu!ar formu!a 04H8.
@raw the disp!a#ed formu!a for each of the three a!enes.
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9. $a% 0#c!ohexane can be con'erted into c#c!ohexene 'ia a three-stage s#nthesis.
s t a g e c o m p o u n d A
s t a g e 2 s t a g e 9
O H
0 l 2
cyclohexne cyclohexnol cyclohexene
$i% "n stage / c#c!ohexane reacts with ch!orine to form the organic product/compound A.
,how the structure of compound A.
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$ii% ,tage 9 in'o!'es the deh#dration of an a!coho!.
,tate a suitab!e reagent for deh#drating an a!coho!.
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$iii% &rite a ba!anced e5uation for the deh#dration of c#c!ohexano!/ 0HOH.
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$b% The reaction in stage is difficu!t to contro!. One other possib!e ch!orinatedproduct is /4-dich!oroc#c!ohexane.This is shown be!ow.
s t a g e c o m p o u n d !
c o m p o u n da n dC "
s t a g e 2 s t a g e 9
0 l
0 l
0 l
2
cyclohexne 1#4$%ichlo&ocyclohexne
/4-@ich!oroc#c!ohexane reacts in the same wa# as compound Ain stages2 and 9.
$i% ,uggest the structure of compound !.
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$ii% Two c#c!ic a!enes/ Cand "are formed in stage 9. Cand "are structura!isomers. ,uggest the structures of Cand ".
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1'. +thano! and g!#cero! $propane-/2/9-trio!% are both produced industria!!# on a !argesca!e.
+thano! is manufactured b# both fermentation and the h#dration of ethene.
C!#cero! is produced as a b#-product of soap manufacture.
H
H
e t h n o l
0 HH
0 O HH
H
H
g l y c e & o l
0 O HH
0 O HH
0 O HH
The re!ati'e!# !ow 'o!ati!it# of a!coho!s such as ethano! can be exp!ained b# theexistence of intermo!ecu!ar bonds.
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$i% +xp!ain what is meant b# the terms
low volatility/ ....................................................................................................
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intermolecular bonds ......................................................................................
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$ii% On the ethano! mo!ecu!es be!ow/ !abe! an# re!e'ant dipo!es/ show theintermo!ecu!ar bond formed and state the t#pe of intermo!ecu!ar bond.
H
H
HH 0
0 O
H
H
H
H
HH
0
0
HO
H
t#pe of intermo!ecu!ar bond ...............................................
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$iii% C!#cero! forms the same t#pe of intermo!ecu!ar bonds as ethano!. =redict/ with areason/ whether the boi!ing point of g!#cero! wi!! be higher or !ower than that ofethano!.
The boi!ing point of g!#cero! wi!! be ................... than that of ethano! because
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11. This 5uestion is about the ha!ogenoa!ane 2-ch!orobutane.
2-0h!orobutane reacts with aOH/ but the products are dependent on the so!'entused.
H
0 0H
H
H
H
H
0 0
0 l
H
H
H
O H $ a 5 % O H $ e t h a n o ! i c %
a ! c o h o ! A a m i x t u r e o f t h r e e a ! e n e s
/ a n d! C "
2-0h!orobutane reacts with OH
in a5ueous conditions to produce a!coho! A.
$i% "dentif# a!coho! A.
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$ii% @escribe/ with the aid of cur!# arrows/ the mo'ement of the e!ectrons in themechanism. ,how an# re!e'ant dipo!es/ !one pairs of e!ectrons and the products.
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12. $a% "n the presence of a suitab!e cata!#st/ c#c!ohexano! reacts with compound(.
The organic product is shown in the e5uation be!ow.
O H + + H 2OO
C
O
co m p o un d Y
organ ic p rod uct
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$i% ,tate a suitab!ecata!#st. ..................................................................................
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$ii% "dentif# compound(.
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$b% 0#c!ohexano! can a!so be oxidised to form c#c!ohexanone.
$i% ,tate a suitab!e oxidising agent for this reaction.
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$ii% &rite a ba!anced e5uation for the oxidation of c#c!ohexano! toc#c!ohexanone.
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$i'% &hen 00s are exposed to strong u!tra'io!et radiation in the upper atmosphere/homo!#tic fission taes p!ace to produce free radica!s.
+xp!ain what is meant b# the term homolyticfission.
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$'% ,uggest which bond is most !ie!# to be broen when 090lis exposed to
u!tra'io!et radiation. +xp!ain #our answer.
bond ................................................................................................................
reason .............................................................................................................
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$'i% "dentif# the twofree radica!s most !ie!# to be formed when 090lis exposed to
u!tra'io!et radiation.
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14. +thano!/ 02H1OH/ can be produced b# the fermentation of g!ucose/ 0H2O.
&rite a ba!anced e5uation for the fermentation of g!ucose.
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15. +thano! has a re!ati'e!# high boi!ing point. This can be exp!ained in terms ofintermo!ecu!ar h#drogen bonds.
@raw a second mo!ecu!e of ethano! a!ongside the one drawn be!ow and show how ah#drogen bond cou!d be formed. 0!ear!# show an# re!e'ant dipo!es and !one pairs of
e!ectrons.
OH
0 H 2 0 H 9
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16. =ropane/ 09H8/ is used in the reaction se5uence shown be!ow.
H9
0 0 H2
0 H9
H9
0 0 H2
0 H2
0 lr e a c t i o n 1
0 E u ' ! i g h tl2
A
H9
0 0 H 0 H2
C
)
"
H9
0 0 H2
0 H2
O Hr e a c t i o n 2
a 5 u e o u s O H E h e a t
r e a c t i o n 3 e t h a n o ! i cO H E h e a t
!
H9
0 0 H
O H
0 H9
r e a c t i o n 4p o ! # m e r i s a t i o n
$a% The reaction se5uence shows se'era! important reaction mechanisms. ,e!ectfrom reactions 1to 4/ the reaction that shows
$i% free radica! substitution/ reaction ..........
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$ii% e!ectrophi!ic addition/ reaction . .........
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$iii% e!imination/ reaction ..........
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$b% "n reaction 2/ the a5ueous OH
acts as a nuc!eophi!e.
$i% ,tate what is meant b# the term nucleophile.
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$ii% 0omp!ete/ with the aid of cur!# arrows/ the mechanism in'o!'ed in reaction 2.,how an# re!e'ant dipo!es.
H90 0H2 0H2 0l H90 0H2 0H2 OH + ..........
OH
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$c% 0ompounds !and "are structura! isomers of each other.
$i% ,tate what is meant b# the term structural isomers.
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$ii% @raw the se!eta! formu!ae of compounds !and ".
0ompound ! 0ompound "
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$d% 0ompound Ccan be po!#merised to form compound ).
$i% ,tate the t#pe of po!#merisation. ............................................................
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$ii% ame compound ). ...............................................................................
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$iii% @raw a section of compound ). ,how tworepeat units.
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17. Acro!ein/ 0H2FF0H0HO/ and acr#!ic acid/ 0H2FF0H0OOH/ are both used in industr#
for the manufacture of p!astic resins and po!#mers. Both acro!ein and acr#!ic acid canbe made from prop-2-en--o!/ 0H2FF0H0H2OH.
$a% $i% @raw the structures of prop-2-en--o! and acro!ein. 0!ear!# disp!a# thefunctiona! groups in each compound.
p&op$2$en$1$ol c&olein
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$ii% ame the functiona! group common to bothprop-2-en--o! and acro!ein.
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$b% =rop-2-en--o! can be oxidised to form either acro!ein or acr#!ic acid.
$i% "dentif# a suitab!e oxidising mixture.
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$ii% &rite a ba!anced e5uation for the oxidation of prop-2-en--o! into acro!ein.
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19. "n this 5uestion/ one mar is a'ai!ab!e for the 5ua!it# of spe!!ing/ punctuation andgrammar.
The rates of h#dro!#sis of ch!oroethane/ bromoethane and iodoethane are different.
@escribe how #ou wou!d monitor the reaction rates.
+xp!ain wh# ch!oroethane/ bromoethane and iodoethane react at different rates.
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21. $a% There are four structura! isomers of 04H:O that are a!coho!s. One of the isomers
has been drawn for #ou.
0omp!ete the tab!e be!ow to show the other structura! isomers.
0H
H
H
0
H H O H
H H H
0 0 H
b*tn$1$ol isomer 1 isomer 2 isomer 3
)9*
$b% Butan--o! is oxidised b# an acidified so!ution of potassium dichromate$"% toform a carbox#!ic acid.
$i% ,tate the co!our change that #ou wou!d see.
0o!our changes from IIIIIII.........I to IIII..II..........
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$ii% &rite a ba!anced e5uation for this oxidation of butan--o! to form acarbox#!ic acid.
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$c% Butan--o! reacts with hot concentrated su!phuric acid to form compound !.
$i% 0ompound !has an empirica! formu!a of 0H2and a re!ati'e mo!ecu!ar
mass of 1.
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22. $a% &rite an e5uation for the combustion of ethano!.
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$b% "n this 5uestion/ one mar is a'ai!ab!e for the 5ua!it# of written communication.
@escribe/ with the aid of e5uations/ the industria! manufacture of ethano! fromg!ucose/ 0H2O/ and from ethene/ 02H4. ame each t#pe of reaction and state
a!! essentia! conditions.
uture supp!ies of ethano! are !ie!# to come from g!ucose rather than fromethene. +xp!ain wh#.
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23. This 5uestion is about the compounds A$Fbe!ow.
$a% Answer the fo!!owing 5uestions b# referring to the compounds A$F.
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$i% &hat is the mo!ecu!ar formu!a of compound "(
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$ii% &hat is the empirica! formu!a of compound C(
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$iii% &hich two compounds are structura! isomers of each other(
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$i'% &hich two compounds are cis-transisomers of each other(
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$b% 0ompound )can be deh#drated to form compound A. 0omp!ete a ba!ancede5uation for this reaction.
H H
H
H
H
H
H
H
O H
0 0 0 0
H
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$c% 0ompound Ccan be deh#drated to form a new compound/ +/ with the mo!ecu!arformu!a/ 04H. ,uggest a structura! formu!a and a name for +.
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24. Ha!ogenoa!anes/ such as -ch!orobutane/ are h#dro!#sed with hot a5ueous a!a!i/
OH
$a5%/ to form a!coho!s.
$a% @escribe/ with the aid of cur!# arrows/ the mechanism of the h#dro!#sis of -
ch!orobutane with OH
$a5% ions to produce butan--o!. ,how an# re!e'ant !onepairs of e!ectrons and dipo!es.
0 H 0 H 0 H 0 H 0 H 0 H
H
0
H
0 l
H
0
H
O H 6 . . . . . . . . . . . . . . . . . . .9 92 22 2
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$b% Another ha!ogenoa!ane/ ,/ has a re!ati'e mo!ecu!ar mass of 27 and has thefo!!owing composition b# mass0/ 97.8K H/ .9K 0l/ 11.GK.
$i% ,how that the empirica! formu!a of compound ,is 02H20l.
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$ii% @educe the mo!ecu!ar formu!a of compound ,.
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$iii% 0ompound ,can a!so be h#dro!#sed with hot a5ueous a!a!i to formbutane-/9-dio!. @raw the structure of butane-/9-dio!
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$i'% @educe the structure of compound ,.
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25. La'andu!o!/ 0:H8O/ is a fragrant oi! which is found in !a'ender. The structura! and the
se!eta! formu!ae of !a'andu!o! are shown be!ow.
0 H
0 H
H H
H
H H0
0
0
00
0O H
H 0
H 0
9
2
9
9
s t & * c t * & l - o & . * l
2
O H
s / e l e t l - o & . * l
$a% $i% "dentif# twodifferent functiona! groups in !a'andu!o!.
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$ii% &h# does !a'andu!o! notha'e cis-transisomerism(
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$b% La'andu!o!/ 0:H8O/ a!so reacts with bromine to form a saturated organic
product.
,tate what #ou wou!d see in this reaction and deduce the mo!ecu!ar formu!a ofthe organic product.
obser'ation .....................................................................................................
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mo!ecu!ar formu!a ...........................................................................................
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$c% La'andu!o! cou!d be con'erted into an ester 0/ which is a!so found in !a'ender oi!.
O
O
0
0 H 9
ester 0
,tate a reagent and a cata!#st that cou!d be used to form ester 0from !a'andu!o!.
reagent ............................................................................................................)*
cata!#st ............................................................................................................
)*
$d% La'andu!oi can be oxidised to produce either compound(or compound .
O
0
! a ' a n d u ! o !
0 H O
c o m p o u n d (
: 0 H O
0 O O H
c o m p o u n d
: 20 H O
: 80 H O
$i% &rite a ba!anced e5uation for the oxidation of !a'andu!o! to producecompound .
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$ii% An infra-red spectrum of either compound(or compound was obtained
and was found to contain an absorption between 8:
71: cm
.Howe'er/ there was no broad absorption between 21:: 99:: cm
.
B# referring to #our Data Sheet/ use this information to deduce whether theinfra-red spectrum was of compound(or of compound . ,how #ourreasoning.
The infra-red spectrum was of compound ............ because ..................
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