WHEN THE NUMBER OF CARBON IN HYDROCARBON

INCREASES/GREATER/HIGHER, THE SIZE OF HC

MOLECULE IS BIGGER.
THUS, THE INTERMOLECULAR FORCES/Van der Waal
FORCES IS STRONGER.
THUS, MORE ENERGY IS NEEDED TO OVERCOME THE
FORCES.
Chemical Properties
Reactivity of alkenes
!. Al"ene # $%re rea&'#(e )e&a*e '+e ,reen&e %- double
covalent bond, (unsaturated hydrocarbon)
.. Al"ene de&%l%*r#/ed ,*r,le %l*'#%n %- acidified potassium
manganate(VII)
0. Al"ene de&%l%*r#/ed redd#+ )r%1n %l*'#%n %- bromin water
2. Ne*'ral.
Combustion of alkenes
.
ddition Reaction (!"#)
$he carbon%carbon double bond is converted into
two single bonds
H H H H

C & C 3 4 Y 4 C C Y

H H H H

Al"ene M%le&*le Al"ane
5Una'*ra'ed6 5Sa'*ra'ed6
7
'" ddition of hydrogen
H H H H
N#/8'
C 9 C 3 H
.
H C C H
!:;
%
C
H H H H
E'+ene H<dr%=en E'+ane
C+e$#&al e>*a'#%n? C
.
H
2
3 H
.
C
.
H
@
EAa$,le *e %- '+# ,r%&e?

Man*-a&'*re %- $ar=ar#ne # '+r%*=+ +<dr%=ena'#%n
#" ddition of halogens
T+e ,r%&e # "n%1n a +al%=ena'#%n
H H H H

C & C 3 Br Br Br C C Br

H H H H
E'+ene Br%$#ne !,.Bd#)r%$%e'+ane
5*na'*ra'ed6 5a'*ra'ed6
C+e$#&al e>*a'#%n? C
.
H
2
3 Br
.
C
.
H
2
Br
.

(" ddition of hydrogen halides
#. Al"ene rea&' 1#'+ +<dr%=en +al#de #n r%%$ &%nd#'#%n.
H<dr%=en +al#de $%le&*le # added '% d%*)le )%nd #n al"ene,
'% ,r%d*&e halogenoalkane.
##. W+en +<dr%=en &+l%r#de =a # ,aed '+r%*=+ #n'% e'+ene,
$%n%&+l%r%e'+ane # ,r%d*&ed.
H H H H

C 9 C 3 HCCl H C C Cl

H H H H
E'+ene H<dr%=en &+l%r#de M%n%&+l%r%e'+ane
5Una'*ra'ed6 5Sa'*ra'ed6

C+e$#&al e>*a'#%n? C
.
H
2
3 HCl D C
.
H
E
Cl
)" ddition of acidified potassium manganate(VII)
!. W+en al"ene # $#Aed 1#'+ a&#d#-#ed ,%'a#*$ $an=ana'e5VII6,
#' ,*r,le &%l%*r # de&%l%*r#ed.
.. T+# # )e&a*e add#'#%n ,r%&e %&&*rred, a =r%*, %-
hydro*yl (%%+,) # added '% '+e $%le&*le %- al"ene '% -%r$ a
$%le&*le %- -diol 5'<,e %- al&%+%l6 1+#&+ # a'*ra'ed and
&%l%*rle.


C 9 C 3 H
.
O C C

OH OH
Al"ene

al"aneBd#%l &%$,%*nd
FOG
F-r%$ a&#d#-#ed ./n+
)
G
5Una'*ra'ed6 5Sa'*ra'ed6
!" 0team
(,ydration process)
!. Al"ene rea&' 1#'+ 'ea$ '% ,r%d*&e e>*#(alen' alcohol
a' '+e 'e$,era'*re %- 0;;
%
C and #n '+e ,re*re %- @;
a'$%,+ere.
.. Rea&'#%n &a'al<' )< &%n&en'ra'ed ,+%,+%r#& a&#d , ,
(
P+
)
.
0. T+# $e'+%d # %ne %- '+e #nd*'r#al ,re,ara'#%n '% ,r%d*&e
al&%+%l.
H H H H

C 9 C 3 HCOH H C C H

H H H OH
E'+ene S'ea$ E'+an%l

(11
o
C, 21 atm
,
(
P+
)

C
.
H
2
3 H
.
O D C
.
H
E
OH H C
.
H
@
O
Physical Properties
!. 3i4uid a' r%%$ 'e$,era'*re. 5,=. @.6 F n% =aG
.. S#$,le al&%+%l are (er< %l*)le #n 1a'er, #n-#n#'e %l*)#l#'<.
Me'+an%l, ethanol dan ,r%,anB!B%l # miscible #n all ,r%,%r'#%n
5'erlar*' &a$,*r den=an a#r dala$ e$*a "adaran6.
T+e re' %- '+e al&%+%l le %l*)le %r #n%l*)le.
5$,6+3
!. 8re,ara'#%n %- e'+an%l.
#. La)%ra'%r< ,re,ara'#%n 5-er$en'a'#%n6
##. Ind*'r#al ,r%d*&'#%n 5+<dra'#%n ,r%&e6
/aking 5thanol 7ermentation
!. T1% 'a=eI
#. Fer$en'a'#%n
##. 8*r#-#&a'#%n
B '+r%*=+ -ra&'#%nal d#'#lla'#%n a' 89
o
C
( boiling point of 5$,6+3)
7ermentation of :lucose
!. Yea' # added '% *=ar %r 'ar&+.
.. naerobic ,r%&e 5 'a"e ,la&e #n '+e a)en&e %- %A<=en6.
0. Yea' releae en/<$e. T+ee en/<$e )rea" d%1n '+e
*=ar/'ar&+ #n'% =l*&%e, C
@
H
!.
O
@
.
2. Z<$ae l%1l< de&%$,%e '+e =l*&%e '% -%r$ e'+an%l and
&ar)%n d#%A#de.
(11
o
C, 21 atm
,
(
P+
)
W+en '+e &%n&en'ra'#%n %- e'+an%l rea&+ !EJ, '+e <ea' d#e.
K? H%1 '% ,r%d*&e ,*re al&%+%lL
A? 8*r#-#ed '+e e'+an%l '+r%*=+ -ra&'#%nal d#'#lla'#%n.
Purification of 5thanol
!. E'+an%l ,r%d*&ed -r%$ '+e -er$en'a'#%n ,r%&e # #$,*re,
)e&a*e #' $#A 1#'+ '+e =l*&%e %l*'#%n.
Del#(er< '*)e
L#$e 1a'er
Bea"er
Gl*&%e 3 <ea'
C%n#&al -la"
Z<$ae H C
.
H
E
OH H C
.
H
@
O
C
2
,
'#
+
2
(a4) #C,
(
C,
#
+, (l) ; #C+
#
(g)
0;
%
C
K ? Dra1 la)eled d#a=ra$ '% &arr< %*' '+e ,*r#-#&a'#%n %- e'+an%l
'+r%*=+ -ra&'#%nal d#'#lla'#%n ,r%&e.
K? W+< '+e %l*'#%n/-#l'ra'e #n r%*nded &%n#&al $*' +ea'ed a'
M:
%
C.
A? T+e )%#l#n= ,%#n' %- e'+an%l # M:
%
C.
K? E'+an%l ,r%d*&ed $a< '#ll &%n'a#n %- %$e 1a'er.
W+a' +%*ld )e d%ne '% )e *re '+a' e'+an%l # !;;J ,*reL
A? An+<dr%* &al&#*$ %A#de %r an+<dr%* &al&#*$ &+l%r#de #
add/,*' #n'% '+e e'+an%l.
N
O
444444444444444
T+er$%$e'er
Fra&'#%n#n=
&%ll*$
L#e)#=
&%ndener
Wa'er #n
Wa'er %*'
8r%d*&' -r%$
-er$en'a'#%n 8%r&ela#n
&+#,
Re'%r' 'and
1#'+ &la$,
D#'#lla'e
5E'+an%l6
B*nen
)*rner
R%*nded
&%n#&al
Wa'er
W#re
=a*=e
K? W+a' # '+e -*n&'#%n %-I
B '+er$%$e'er
B ,%r&ela#n &+#,
B L#e)#= &%ndener
A? '+er$%$e'er # *ed '% en*re '+a' 'e$,era'*re # al1a<
a' M:
%
C.
B? 8%r&ela#n &+#, # *ed '% a(%#d '+e %l*'#%n P*$,ed/
e--er(een&e 5)rea"#n= )*))le6
C? T% &%%led '+e e'+an%l (a,%*r '% )e&%$e l#>*#d.
K? Na$ed '+e ,r%&e #n L#e)#= &%ndener.
A? C%ndena'#%n
K? W+a' # '+e ,r%,er'#e %- e'+an%l
A? 8r%,er'#eI
B &%l%*rle
B (%la'#le
B =%%d %r=an#& %l(en'
B $#&#)le 1#'+ 1a'er
B +#=+l< -la$$a)le
B an'#e,'#&
B &+e$#&all< rea&'#(e
K? W+a' # '+e *e %- e'+an%l
A? UeI
B A a %l(en' #n ,er-*$e/&%$e'#&
B A a '+#nner #n (arn#+, #n"
B A a &leaner -%r &%$,a&' d#&.
B A a -*el -%r 'ran,%r'
B A a ra1 $a'er#al -%r '+e $an*-a&'*re %- (#ne=ar,
B A a ra1 $a'er#al '% $a"e #nd*'r#al ,r%d*&' *&+ a
an'#e,'#& and &%*=+ <r*,.
Industrial production of ethanol
E'+ene # $#A 1#'+ 'ea$ # ,aed '+r%*=+ concentrated
phosphoric acid (catalyst) a' (11
o
C 5'e$,era'*re6 and 21
atmosphere 5,re*re6.
,
(
P+
)

< C
#
,
)
concentrsted C
#
,
!
+,
C,
#
& C,
#
; ,
#
+ =====> C,
(
C,
#
+,
(11
o
C, 21 atm
Chemical Properties
'" Combustion
#. Al&%+%l are (er< -la$$a)le *'an&e.

##. E'+an%l )*rn 1#'+ n%nB$%"< and )l*e -la$e and releae
l%' %- +ea'. S*#'a)le -%r *e a -*el, de&r#)ed a &lean -*el.
K? Wr#'e &%$)*'#%n e>*a'#%n -%r +eAan%l
#" +*idation
#. E'+an%l &an )e %A#d#ed #n'% e'+an%#& a&#d )< an %A#d##n= a=en'.
FE'+an%#& a&#d # a -a$#l< %- &ar)%A#l#& a&#dG
C
#
,
!
+, ; (+
#
#C+
#
; (,
#
+
5thanol +*ygen Carbon ?ater
dio*ide
C
2
,
'(
+, ; @+
#
2C+
#
; 8,
#
+
he*anol +*ygen Carbon ?ater
dio*ide
C,
(
C,
#
+, ; #A+B C,
(
C++, ; ,
#
+
5tanol 5thanoic acid
K? S+%1 '+e 'r*&'*ral -%r$*la -%r '+e e>*a'#%n a)%(e.
K? Na$ed . %l*'#%n are &%$$%nl< *ed a %A#d##n= a=en'.
5#6 A&#d#-#ed ,%'a#*$ $an=ana'e5VII6, QMnO
2

5purple '% &%l%*rle / de&%l%*r#ed6
5##6 A&#d#-#ed ,%'a#*$ d#&+r%$a'e5VI6, Q
.
Cr
.
O
M

5orange '% green6
K? Dra1 a la)eled d#a=ra$ -%r '+e ,r%&e.
H H H O
R C R S
H T C T C T OH 3 .FOG D H T C T C T OH 3 H
.
O
R C R
H H H
Hea'
E'+an%l 3
,%'a#*$ d#"r%$a'5VI6 3
d#l*'e *l-*r#& a&#d
C%ld
1a'er
D#'#lla'e
5e'+an%#& a&#d6
D#'#lla'e 5e'+an%#& a&#d6

B C%l%*rle
B V#ne=ar $ell
B Bl*e l#'$* ,a,er '*rn red 5a&#d#& ,r%,er'#e6
(" Dehydration
ALCOHOL D ALQENE
!. C%n(er'ed ethanol into ethene and a molecule of water"
.. T+e el#$#na'#%n %- 1a'er re*l' '+e -%r$a'#%n %- a &ar)%nB
&ar)%n d%*)le )%nd.
0. De+<dra'#%n %&&*r 1+en
a. e'+an%l (a,%*r # ,aed %(er a +ea'ed &a'al<' *&+ a.
#B 8%r%* ,%' / ,%r&ela#n &+#,
##B 8*rn#&e '%ne / al*$#n#*$ %A#de, Al
.
O
0
/al*$#na
). E'+an%l # +ea'ed *nder re-l*A a' !M;
%
C 1#'+ eA&e
&%n&en'ra'ed *l,+*r#& a&#d.
CH
0
CH
.
OH CH
.
9 CH
.
3 H
.
O
5thanol 5thene
B H
.
O
K ? Dra1 '+e 'r*&'*ral $%le&*le -%r '+e ,r%&e
K ? Dra1 la)eled d#a=ra$.
8re,ared )<I
Qa$al Ar#--#n B#n Saa#$
SMQDBL
+'',?//"e$+a1".1e).&%$
Hea'
Gla 1%%l
%a"ed 1#'+
e'+an%l
Hea'
E'+ene
=a
Wa'er
8%r&ela#n
&+#,
Re'%r'
'and
1#'+
&la$,
Te'
'*)e
Del#(er<
'*)e
H H H H
R R R R
H T C T C T H D H T C U C T H 3 H
.
O
R R
H OH
5thanoic sid
Can )e ,re,ared '+r%*=+ o*idation %- an e'+an%l.
C+e$#&al e>*a'#%n?
T+# # &arr#ed %*' )< reflu*ing ethanol 1#'+ an
o*idising agent *&+ a a&#d#-#ed ,%'a#*$
d#&+r%$a'e5VI6 %r ,%'a#*$ $an=ana'e5VII6
%l*'#%n.
H H
V V
H T C T C T OH

V V
H H
H O
V S
H T C T C T OH

V
H
3 .FOG 3 H
.
O
.
#
Cr
#
+
8
solutions
;
dilute ,
#
0+
)
reflu*
C,
(
C,
#
+, ; #A+B C,
(
C++, ; ,
#
+
5tanol ethanoic acid
8re,ara'#%n %- e'+an%#& a&#d '+r%*=+ re-l*A#n=
C%ndener # *ed '% ,re(en' '+e l% %- a (%la'#le
l#>*#d )< (a,%r#a'#%n.
T#el '*)e
Wa'er %*'
AAAAAAAAAAAAAA
La)el '+e
d#a=ra$ ,leae
Wa'er
#n
L#e)#= &%ndener
R%*nded )%''%$ -la"
Re'%r'
'and
A)%l*'e e'+an%l, C
.
H
E
OH 3
A&#d#-#ed ,%'a#*$ d#&+r%$a'e5VI6,
Q
.
Cr
.
O
M
%l*'#%n
Hea'
W#re
=a*=e
T+# $e'+%d %- re'a#n#n= a (%la'#le l#>*#d d*r#n=
+ea'#n= # &alled re-l*A#n=.
H%1 '% &arr< %*' '+e a&'#(#'<L
8+<#&al 8r%,er'#e
B ,H le '+an M
B +ar, %r *n,leaan' $ell
B '*rn $%#' )l*e l#'$* ,a,er '% red
B &%l%*rle l#>*#d
Rea&'#%n 1#'+ al&%+%l FE'er#-#&a'#%nG
E'er#-#&a'#%n?
Car)%A#l#& a&#d rea&' 1#'+ al&%+%l '%
,r%d*&e an e'er and 1a'er.
Concentrated H
2
SO
4
? &a'al<'
Concentrated
H
2
SO
4

Carbo*ilic acid 3 lcohol TTT 5ster 3 ?ater
F1#ll d#&* $%re #n neA' &+a,'erG
Ue %- &ar)%A#l#& a&#d?
#. E'+an%#& a&#d # "n%1n a a&e'#& a&#d *e #nI
B F%%d -la(%r#n=
B F%%d ,reer(a'#(e
B T% $a"e dr*=, d<e, ,a#n' #ne&'##de,
,la'#&
B T% $a"e e'er -%r *e a l%(en'
##. Me'+an%#& a&#d # *ed '% &%a=*la'e la'eA.
###. Ben/%#& a&#d # *ed a -%%d ,reer(a'#(e
50$5R
R ? al"<l =r%*, #n &ar)%A#l#& a&#d
RW ? al"<l =r%*, #n al&%+%l

E'er#-#&a'#%n
B Car)%A#l#& a&#d rea&' 1#'+ al&%+%l '% ,r%d*&e
e'er and 1a'er.
B T+e -*n&'#%nal =r%*, %- e'er # &ar)%A#la'e
=r%*,.
B C%n&e'ra'ed *l,+*r#& a&#d # &a'al<'.
B Car)%A#l#& a&#d l%e XOHW and

+
E
C
n
,
#n ; '
C = +, 3 C
m
,
#m;'
+,
5&ar)%A#l#& a&#d6 5al&%+%l6
+
E
C
n
,
#n ; '
C = + = C
m
,
#m;'
3 ,
#
+
(50$5R)
B Al&%+%l l%e XHW
B T+e )%nd '+a' X)rea" *,W 1#ll XreP%#nW a=a#n
Na$#n= E'er
EAa$,le? #. E'+an%#& a&#d 3 $e'+an%l
$e'+<l e'+an%a'e 3 1a'er
C+e$#&al e>*a'#%n?
, +
C E
, = C = C = +,
C
,
C,
(
C++,
(5tanoic acid)
,
C
,= C = +,
C
,
C,
(
+,
(/ethanol)
3
C,
(
C++, ; C,
(
+, > C,
(
C++C,
(
; ,
#
+
, + ,
C E C
, = C = C = + = C = , ; ,
#
+
C C
, ,
C,
(
C++C,
(

(/ethyl ethanoat) ?ater
8re,ara'#%n %- e'er '+r%*=+ re-l*A
A-'er )%#l#n=, L#e)#= &%ndener # rearran=ed
T% &arr< %*' '+e -ra&'#%nal d#'#lla'#%n a'
M2
%
C Y M:
%
C '% &%lle&' e'+<l e'+an%a'e.
444444444444444
T#el '*)e
L#e)#=
&%ndener
E'+an%l 3
e'+an%#& a&#d 3
&%n&en'ra'ed
*l,+*r#& a&#d
8%r&ela#n &+#,
Wa'er
)a'+
Wa'er
#n
Wa'er
%*'
T% ,re(en'
bumping and
en*re $%%'+
)%#l#n=
T% &%ld '+e
e'+an%l and
e'+an%#& a&#d
Un#-%r$
+ea'#n=
8+<#&al ,r%,er'#e %- e'+<l e'+an%a'e
B &%l%*rle
B -ra=ran' $ell
B #n%l*)le #n 1a'er
B lee dene #n 1a'er
Na'*ral S%*r&e
B M%' #$,le e'er are -%*nd #n -r*#' and
-l%1er.
eA? )en/<l e'+an%a'e #n Za$#ne
e'+<l )*'an%a'e #n ,#nea,,le
B 8al$ %#l are l#>*#d e'er.
B T+e +#=+er and &%$,leA e'er d%e n%'
,r%d*&e ,leaan' $ell
Ue %- e'er
B '% $a"e ,er-*$e, &%$e'#&
B '% $a"e ar'#-#&#al -%%d -la(%r#n=
FTeA' B%%"? Ta)le ..: ,= :!G
B *ed a %r=an#& %l(en'
e=. e'+<l e'+an%a'e *ed #n *n)*rn
l%'#%n, ,%l#+ re$%(er, =l*e.
B '% $a"e <n'+e'#& ,%l<$er/-a)r#&
B '% $a"e a,#r#n 5,a#n rel#e(er6