Organic Chemistry Homework 2 - Alkanes and

Alkenes
Name: . Mark: / 100
Class: .. Date:
.
Paper 2 [Structured and Free Response Questions]
Section A [Structured Questions]
1 The table shows some data about the first six members of the alkane homologous series.
alkane number of
carbon atoms
in one molecule
X
melting
point /
o
C
boiling
point /
o
C
heat energy released by
complete combustion of
1 mole of alkane / kJ
Y
methane 1 1!" 1#" !!0
ethane " 1!$ !% 1&'0
(ro(ane $ 1!! '" ""00
butane ' 1$! 0 "!!0
(entane & 1$0 $# $&00
hexane # %& #% '1'0
)a* +lot a gra(h of Y against X on the gra(h grid below. ,$-
)b* .se the gra(h to estimate the /alue of Y for (entane. 0rite 1our answer in the
table.
1
number of carbon atoms in one molecule
heat energy
released by
compl ete
combusti on of
1 mole of
alkane / kJ
,"-
)2* Cal2ulate the energ1 released b1 one gram of methane.
3mount of energ1 released 4 1/,1"5')1*- !!0 k6
4 && k6
,1-
)d* 7i/e the mole2ular formula of an alkane whi2h is a li8uid at room tem(erature and
and (ressure )"&
o
C and 1 atmos(here*.
C
&
9
1"
/ C
#
9
1'
,1-
)e* Draw the stru2tural formula of four (ossible isomers of hexane.
,:efer to this /ideo on 1outube: htt(://www.1outube.2om/wat2h;/48<h=6>'.mds
?t gi/es an ex2ellent ex(lanation to the isomers of hexane@ Control2li2k on the h1(erlink
abo/e.-
,'-
)f* 0hat is the differen2e in the formula of two successive members of an homologous
series;
Two su22essi/e members of an homologous series differ b1 one unit of C9
"
.
,1-
" Cra2king is used to break big h1dro2arbon mole2ules into smaller ones.
)a* )i* Atate the 2onditions for 2ra2king.

3 high tem(erature and a solid 2atal1st )su2h as aluminium oxide or sili2on)?B*
oxide*
)ii* Atate and ex(lain one ad/antage to motor /ehi2les of 2ra2king.
Cra2king (rodu2e small alkane mole2ules that 2an be used as fuel for motor
/ehi2les. Cra2king of big h1dro2arbon mole2ules from (etroleum into smaller
alkane mole2ules that 2an be used as (etrol for 2ars. +etroleum does not 2ontain
enough small alkane mole2ules to (ro/ide all the worldCs (etrol.
)b* 3 h1dro2arbonD C
1'
9
$0
D is 2ra2ked to gi/e two (rodu2ts. <ne of the (rodu2ts is
(ro(ane.
)i* 0hat is the mole2ular formula of the other (rodu2t;
C
11
9
""
2
)ii* Des2ribe a 2hemi2al test to show that the other (rodu2t is unsaturated.

test:

3dd the li8uid (rodu2t into a8ueous bromine in a test tube and shake.
observation in test:
?f the (rodu2t is unsaturatedD the reddish brown a8ueous bromine will turn
2olourless ra(idl1.
,"-
$ )a* 3n alkene has the mole2ular formula C
&
9
10
. This alkene rea2ts with bromine to form
a 2om(ound with the stru2tural formula shown below.
9 9 9 9 9
9 C C C C C 9
9 Er Er 9 9
)i* Draw the stru2tural formula of C
&
9
10
.
)ii* 0rite the e8uation for the rea2tion of between C
&
9
10
and bromine.
C
&
9
10
5 Er
"
C
&
9
10
Er
"
)iii* 7i/e the 2olours of
the alkene: 2olourless

bromine: reddishbrown

the product of the reaction: 2olourless

)i/* =x(lain wh1 this rea2tion is 2alled an addition reaction.
The bromine mole2ule is added to the alkene mole2ule to form a single mole2uleD
and a saturated mole2ule is obtained.
,NE: 3n addition rea2tion is a rea2tion in whi2h two or more mole2ules Foin
together to form a single mole2ule. 3 saturated mole2ule is obtained.-
,G-
)b* The mole2ular formulas of the first three members of an homologous series of
h1dro2arbons are:
3
C
'
9
#
C
&
9
!
C
#
9
10
)i* 0hat is the mole2ular formula of the next member of this series;
C
G
9
1"
)ii* Auggest a (h1si2al (ro(ert1 of these h1dro2arbons whi2h is likel1 to 2hange
as the number of 2arbon atoms in2reases. 9ow does it 2hange;
Eoiling (oint. The boiling (oints of these h1dro2arbon in2rease as the number of
2arbon atom in2reases.
,"-
' The diagram shows how margarine is (rodu2ed from /egetable oil.
9 9 9 9 9 9 9 9 9 9 9 9 9 9
9
"
5 C C C C C C C C
ni2kel
h1drogen C C (owder C C
9 9 9 9 9 9 9 9
(art of a /egetable oil mole2ule (art of a margarine mole2ule
)a* 0hat t1(e of rea2tion takes (la2e between h1drogen and /egetable oil;
3ddition rea2tion.

,1-
)b* )i* 0hat is the (ur(ose of the ni2kel in this rea2tion;
The ni2kel a2ts as the 2atal1st in this rea2tion.
)ii* 0h1 is the ni2kel in powder form;
Ni2kel (owder has smaller (arti2le siHe and a larger surfa2e area. =x(osing a larger
surfa2e area for 2ollisions between rea2ting (arti2les results in more 2ollision (er unit
time. 0ith more 2ollisionsD the number of effe2ti/e 2ollisions (er unit time in2reases. The
s(eed of rea2tion in2reases.
,"-
)2* Aome /egetable oil mole2ules 2ontain more than one C4C bond. The number of
C4C bonds in a /egetable oil mole2ule 2an be found b1 rea2ting the oil with iodine.
?odine rea2ts with C4C bonds in the same wa1 as bromine. 0.0& mole of a /egetable
oil was found to in2rease its mass b1 "&.' g when shaken with an ex2ess solution of
iodine. 9ow man1 C4C bonds are 2ontained in one mole2ule of the oil;
4
Number of moles of iodineD ?
"
D rea2ted 4 "&.' / ")1"G*
4 0.1 mol
0.0& mole of /egetable oil rea2ts with 0.1 mole of iodineD ?
"
ThusD 1 mole of /egetable oil will rea2t with 0.1/0.0& 4 " mole of iodineD ?
"
<ne mole2ule of the oil 2ontained " C4C bonds.

,"-
& Man1 useful (rodu2ts 2an be made from 2rude oil )(etroleum*. This is shown in the
flow 2hart below.
)a* Name
)i* (ro2ess X: fra2tional distillation
)ii* rea2tion Y: 2ra2king
,"-
)b* Ior rea2tion ZD
)i* what t1(e of rea2tion takes (la2e; 3ddition rea2tion
(ii) write the e8uation for the rea2tion: C
"
9
'
5 9
"
< C
"
9
&
<9
,"-
)2* Eutane forms two isomers. Draw the stru2tural formula of both isomers.
,:efer to this website for the isomers of butane: htt(://www.g2ses2ien2e.2om/o"$.htm
3gainD 2ontrol2li2k on the link@-
,"-
)d* Eutane is used as J21linder gasC for 2ooking.
)i* Constru2t the e8uation for the 2om(lete 2ombustion of butane in air.
"C
'
9
10
)g* 5 1$<
"
)g* !C<
"
)g* 5 109
"
<)l*
)ii* 0h1 is good /entilation im(ortant when J21linder gasC is being used;
5
+etroleum
.seful fuels
e.g. butaneD
J21linder gasC
=theneD C
"
9
'
=thanolD C
"
9
&
<9
(ro2ess X
rea2tion Y
rea2tion Z
7ood /entilation ensures that enough ox1gen is a/ailable for 2om(lete
2ombustion of butane. ?f insuffi2ient ox1gen is (resentD in2om(lete 2ombustion
of butane o22urs and (oisonous 2arbon monoxide gas will be (rodu2ed.
# The following 8uestions refer to 2om(ounds with the stru2ture drawn below.
.sing the letters A to as a((ro(riateD answer the following 8uestions.

)a* 0hi2h 2om(ound is an unsaturated h1dro2arbon; D
)b* 0hi2h 2om(ounds are members of the same homologous series;
3 and I
)2* 0hi2h 2om(ounds are isomers of ea2h other; C and =
)d* 0hi2h 2om(ound is a (rodu2t of the rea2tion of ethene with steam; E
)e* C
1#
9
$'
undergoes 2ra2king to (rodu2e C
1$
9
"#
and another 2om(ound. 0hat is the
other 2om(ound; I
,&-
Section B [Free Response Questions]
1 )a* 7i/e the stru2ture of methane.
C

,1-
!
)b* Methane undergoes a rea2tion with 2hlorine.
)i* Atate the t1(e of rea2tion that takes (la2e and one im(ortant 2ondition for
the rea2tion.
Aubstitution rea2tion. The im(ortant 2ondition is that the mixture of methane and
2hlorine gas is ex(osed to diffused sunlight or ultra/iolet light.
)ii* Draw the stru2tures of an1 two organi2 (rodu2ts of this rea2tion and write an
e8uation for the rea2tion (rodu2ing one of them.
C

Cl
C

Cl
Cl
C

Cl Cl
Cl
C
Cl
Cl Cl
Cl
,an1 "-
C9
'
5 Cl
"
C9
$
Cl 5 9Cl
C9
$
Cl 5 Cl
"
C9
"
Cl
"
5 9Cl
C9
"
Cl
"
5 Cl
"
C9Cl
$
5 9Cl
C9Cl
$
5 Cl
"
CCl
'
5 9Cl
,an1 1 e8uation-

)2* Methane is the first member of a homologous series. 3nother homologous series
has the general formula C
n
9
)"n #*
D where n is a number greater than &. 7i/e the
formulas of the first two members of this series.
C
#
9
#
D C
G
9
!
,"-
" <ne of the 2om(ounds in 2rude oil is dode2aneD C
1"
9
"#
.
)a* <ne of the rea2tions of dode2ane is shown in the e8uation below.
C
1"
9
"#
C
!
9
1!
5 C
'
9
!
)i* 0hat is the name of this t1(e of rea2tion; Cra2king
)ii* Atate two 2onditions re8uired for this rea2tion.
3 high tem(erature and a solid 2atal1st )su2h as aluminium oxide or sili2on)?B*
oxide*
"
)iii* ?n the rea2tionD 1.00 mol of dode2aneD C
1"
9
"#
D gi/es onl1 "".! g of o2taneD
C
!
9
1!
. Cal2ulate the (er2entage 1ield.
1 mole of dode2aneD C
1"
9
"#
D (rodu2e 1 mole of o2taneD C
!
9
1!
Theoreti2al mass of o2tane (rodu2ed 4 1 ,!)1"* 5 1!)1*-
4 11' g
ThusD (er2entage 1ield 4 "".!/11' 100K
4 "0 K
,&-
)b* )i* Draw the stru2tural formulas of two isomers of C
'
9
!
.
,:efer to this website: htt(://www.g2ses2ien2e.2om/o"G.htm -
)ii* Auggest one use of these isomersD other than as fuels.
The isomers 2an be (ol1merised to make (lasti2. / The isomers 2an rea2t with
steam to make al2ohol.
,$-
)2* <2tane is a saturated h1dro2arbon and buteneD C
'
9
!
D is an unsaturated
h1dro2arbon. =x(lain how a8ueous bromine 2an be used to distinguish between
these two 2om(ounds.
3dd the li8uid o2tane into a8ueous bromine in a test tube and shake. Ain2e o2tane is
saturatedD no /isible 2hange will be obser/ed and the reddishbrown a8ueous
bromine is not de2olourised.
Eubble the gaseous butene into a8ueous bromine in a test tube. Ain2e butene is
unsaturatedD the reddishbrown a8ueous bromine will de2olourise ra(idl1.

,"-
$ 3n organi2 li8uid L has the following 2om(osition b1 mass:
2arbon M !".G#K h1drogen M 1G."'K
?ts relati/e mole2ular mass is &!.
)a* Determine the em(iri2al formula of L.
C 9
+er2entage b1 mass !".G# 1G."'
3
r
of element 1" 1
Di/ide (er2entage b1
3
r
!".G#/1" 4 #.!%##G 1G."'/1 4 1G."'
Di/ide b1 smallest #.!%##G/#.!%##G 4 1 1G."'/#.!%##G 4
#
number ".&
Aim(lest ratio " &
ThusD the em(iri2al formula of L is C
"
9
&
)b* 9en2eD determine the mole2ular formula of L.
mole2ular formula of L 4 )C
"
9
&
*
n
n 4 &! / ,")1"* 5 &)1*-
4 "
ThusD the mole2ular formula of L is )C
"
9
&
*
"
4 C
'
9
10
)2* Draw the full stru2tural formula and name two (ossible isomers of L.
,:efer to this website for the isomers of butane: htt(://www.g2ses2ien2e.2om/o"$.htm
3gainD 2ontrol2li2k on the link@-
)d* 0rite a balan2ed e8uation for the 2om(lete 2ombustion of L.
"C
'
9
10
)g* 5 1$<
"
)g* !C<
"
)g* 5 109
"
<)l*
)e* Des2ribe what 1ou would obser/e when a sam(le of L is shaken with a8ueous
bromine in a test tube.
0hen L is shaken with a8ueous bromine in a test tubeD no /isible 2hange will be
obser/ed and the reddishbrown a8ueous bromine is not de2olourised.
,G-
' 3rtifi2ial rubber is made from the 2om(ound below.

)a* )i* 0hat is the mass of 1 mole of the 2om(ound;
Mass of 1 mole of the 2om(ound 4 1 M
r
of 2om(ound
4 1 ,&)1"* 5 !)1*-
4 #! g

)ii* 0hat maximum /olume of h1drogenD measured at r.t.(.D would 1ou ex(e2t to
rea2t with 1.$# g of the 2om(ound;
$
Number of moles of the 2om(ound 4 1.$#/#!
4 0.0" mol
<ne mole of the 2om(ound rea2ts with " moles of h1drogen gasD 9
"
ThusD number of mole of h1drogen that would rea2t 4 " 0.0"
4 0.0' mol
Bolume of h1drogen that would rea2t 4 0.0' "' dm
$
4 0.%# dm
$
,'-
)b* Draw the stru2ture of one isomer of the 2om(ound.
<ne (ossible isomer:
,1-
1%