ALKENES

ALKENES
12.
12.
2
2

General formula C
n
H
2n
, n 2.

Functional group double bond C=C

Unsaturated
Unsaturated hydrocarbon

Each carbon atom ( C=C ) is sp

2

hybridized
hybridized.

Restricted rotation of carboncarbon

double bond causes cistrans isomerism

!U"#C $omenclature
!U"#C $omenclature
%etermine the parent name by
selecting the longest chain that
contains the double bond and
change the ending &ane' in al(ane
to &ene'.
Step 1

)hen the chain contains more
than three carbon atoms, a
number is need to indicate the
location of the double bond.
*he chain is numbered starting
from the end closest to the
double bond..
Step 2

CH
2
6
CH
2
7
CH
3
8
CH
2
5
CH
4
CH
3
CH
2
2
CH
3
1
+octene ,not -
octene.

!ndicate the position of the substituent
by the number of the carbon atoms to
/hich they are attached.
C
2
CH
3
CH
3
4
C H
3
1
CH
3
2methyl2butene
,not +methyl2butene.
Step 3

C
2
CH
3
CH
2
4
C H
3
1
CH
3
CH
5
CH
3
6
CH
3
2,-dimethyl2he0ene
,not 2,-dimethyl1
he0ene.

*he ending of the al(enes /ith more
than one double bond should be
change from ene to

diene 2 if there are t/o double bonds

triene 2 if there are three double bonds

Step 4

CH
2
CH
3
C H
2
1
CH
2
4
C H
2
1
CH
2
CH
3
CH
4
CH
5
CH
6
CH
3
7
3,+butadiene
3,+,-heptatriene
MORE MORE

!n cycloal(enes 4
$umber the carbon atoms /ith a
double bond as 3 and 2, in the
direction that gi5es the substituent
encountered first /ith a small
number.
Step 5

5
1
4
2
3
CH
3
3methylcyclopentene
,not 2methylcyclopentene.

+,-dimethylcyclohe0ene
,not 1,6dimethylcyclohe0ene.
MORE MORE
2
3
1
4
6
5
CH
3 CH
3

*/o fre7uently encountered al(enyl
groups are 5inyl group and allyl
group.
RCH=CHR RCH=CH
al(ene al(enyl
CH
2
=CH CH
2
=CHCH
2

5inyl group
5inyl group
allyl group
allyl group
Step 6
-H

)hen t/o identical groups are
attached4
a. on the same side of the double
bond, the compound is cis
b. on the opposite sides of double
bond, it is trans.
cis / trans
cis / trans
Step 7

C C
Cl
H H
Cl
C C
Cl
H Cl
H
cis3,2dichloroethene
trans3,2dichloroethene

CH
3
CH
3
i!e "#$%C names &or the &o''o(in) a'*enes
i!e "#$%C names &or the &o''o(in) a'*enes
2)
1)

CH
3
CH
2
CH
3
3)
4)
CH
3
CH=CHCH
2
C(CH
3
)
2
CH
3
5)

$reparation o& a'*enes
a. %ehydration of alcohols
b. %ehydrohalogenation of al(yl halide


%ehydration of alcohols
%ehydration of alcohols

%'coho's react (ith stron) aci+s in the

presence o& heat to &orm a'*enes an+
(ater.
C C
H OH
H
2
SO
4
(conc.)
C C
,
H
2
O

Concentrated sulphuric acid ,H
2
89
1
. or
phosphoric acid ,H
+
"9
1
. 4 as acidic
catalysts and dehydrating agents.

*he ma:or product is the

most stable
most stable
al(ene, /hich has greater number of
al(ene, /hich has greater number of
al(yl group attach to C=C is follo/
al(yl group attach to C=C is follo/
8aytzeff's rule.
8aytzeff's rule.

Saytzeffs Rule
Saytzeffs Rule
%n e'imination -s-a''. )i!es the most
stab'e a'*ene pro+-ct/ common'. the
most hi)h'. s-bstit-te+ a'*ene.

;0amples
;0amples
,3.
,
2.
,
CH
3
CH
2
OH
H
2
SO
4
(conc.)

C H
2
CH
2
H
2
O
C H
3
CHCH
3
OH
H
2
SO
4
(conc.)

C H
2
CH CH
3
,
H
2
O

CH
3
CH=CHCH
3
(major product)
CHCH
2
CH
3
C H
3
OH
H
2
SO
4
(conc.)

,
CH
2
=CHCH
2
CH
3
(minor product)
,
H
2
O
<echanism for the
<echanism for the
dehydration of alcohol
dehydration of alcohol

8tep 34
$rotonation o& a'coho'
$rotonation o& a'coho'.
C H
3
C CH
2
CH
3
OH
H
H
:
+
,
O H
H
:
..
C H
3
C CH
2
CH
3
OH
H
:
..
,
+
H
O H
H
:

8tep 24
0ormation o& carbocation
0ormation o& carbocation
C H
3
C CH
2
CH
3
OH
H
H
:
+
carbocation
3
2 3
H
C H C
+
CH CH
,
O H
H
:
..

8tep +4
0ormation o& a'*enes
0ormation o& a'*enes
C
O H
H
,
:
..
C C
3
H
+
CH
H
H
H H
H
a
b
1oot a 2 ma3or pro+-ct
1oot b 2 minor pro+-ct

stab'e a'*enes
C C
CH
3
H H
C H
3
,
H
O H
H
:

,
CH
2
=CHCH
2
CH
3
(minor product)

Rearrangement %uring
Rearrangement %uring
%ehydration of #lcohol
%ehydration of #lcohol
;0ample 34
C C CH
3
C H
3
CH
3
CH
3
OH
H
H
2
SO
4
(conc.)

(major product)
C C CH
3
C H
3
CH
3
CH
3
,
(minor product)
C CH CH
3
C H
2
CH
3
CH
3

8tep 3 and 8tep 2 are simi'ar to
the pre!io-s e4amp'e.

8tep +4

$o/ the
rearrangement
rearrangement occurs.

*he less stable, secondary carbocation

rearrange to form more stable tertiary
carbocation.

2
o
carbocation 3
o
carbocation
('ess stab'e) (more stab'e)
C H
3
C C

CH
3
CH
3
CH
3
H r!arran"!m!nt
r!arran"!m!nt
C

C CH
3
C H
3
CH
3
H
CH
3

*he
rearrangement
rearrangement occurs through the
migration of an al(yl group ,methyl.
from the carbon atom ad:acent to the
one /ith the positi5e charge.

=ecause a group
migrates from the one
migrates from the one
carbon to the ne0t
carbon to the ne0t, this (ind of
rearrangement is often called a
3,2
3,2
shift.
shift.

(a)
C CH CH
3
C H
2
CH
3
CH
3
(minor product)
l!## #ta$l! al%!n!
($)
C C CH
3
C H
3
CH
3
CH
3
(major product)
mor! #ta$l! al%!n!
(a)
O H
H
:
..
C
+
C CH
3
C H
CH
3
H CH
3
,
($)
H
H

*he final step can occur in t/o
/ays4
"ath ,a.4 leads to less stable,
disubstituted al(ene and produces
the minor product of the reaction.
"ath ,b.4 leads to highly stable
tetrasubstituted al(ene and produces
the ma:or product according to the
8aytzeff's rule.

C C CH
3
C H
3
CH
3
H OH
H
H
2
SO
4
(conc)
C CH
2
C H
2
CH
3
CH
3
C CH CH
3
C H
3
CH
3
,
(major product)
(minor product)

*ry this>

,2. %ehydrohalogenation of #l(yl Halides
,2. %ehydrohalogenation of #l(yl Halides

5he
e'imination
e'imination

o& a
h.+ro)en
h.+ro)en an+ a
ha'o)en
ha'o)en &rom an a'*.' ha'i+e to &orm an
a'*ene.

Sa.t6e&&7s r-'e
Sa.t6e&&7s r-'e is -se+ to +etermine the
ma3or pro+-ct
C C
H &
,
'OH
alco(ol
r!)lu*
C C
,
H&

;0amples4
,3.
CH CH
2
CH
2
C H
3
CH
3
Cl
,
'OH
alco(ol
r!)lu*
CH CHCH
2
C H
3
CH
3
(major product)
,
CHCH
2
C H
2
CH
2
CH
3
(minor product)

,2.
'OH
alco(ol
r!)lu*
C H
3
CHCH
3
+r
,
C H
2
CHCH
3

,+.
'OH
alco(ol
r!)lu*
CH
CH
3
+r
,
CH
CH
3
,
CH
2
CH
3
(minor product)
(major product)

(4)
CH
3
H
CH
3
C C CH
3
, 89H a'coho'
CH
3
C' re&'-4
CH
3
H CH
3

CH
2
C C CH
3
CH
3
C C CH
3

CH
3
CH
3


2/3-+imeth.'-1-b-tene 2/3-+imeth.'-2-b-tene
(minor pro+-ct) ( ma3or pro+-ct)
2 a'*.' )ro-ps 4 a'*.' )ro-ps

Chemical Reaction of #l(enes
Chemical Reaction of #l(enes
Comparison of *he Reacti5ity =et/een
Comparison of *he Reacti5ity =et/een
#l(anes and #l(enes
#l(anes and #l(enes

%'*enes are more reacti!e

%'*enes are more reacti!e compare+ to a'*anes.

%'*anes ha!e carbon-carbon sin)'e bon+s (?

bonds) (hi'e
a'*enes ha!e carbon-carbon
a'*enes ha!e carbon-carbon
+o-b'e bon+s (
+o-b'e bon+s (
:
:
bonds
bonds
).
).

5he +o-b'e bon+ is a site o& hi)h e'ectron

+ensit. (
n-c'eophi'ic
n-c'eophi'ic).

5here&ore most a'*enes reactions are

electrophilic additions
electrophilic additions
.
.

;lectrophilic #dditions
;lectrophilic #dditions
<echanism
<echanism
C C
H
H H
H
,
; <
C C
@
H H
H
; H
,
<

slow

C C
@
H H
H
; H
,
<
fast
C C H H
H
; <
H

;0ample4
C C
C H
3
C H
3
CH
3
CH
3
,
H Cl
C C
+
CH
3
C H
3
H
CH
3
CH
3
,
Cl
-
#lo,
i.

C C CH
3
C H
3
CH
3
H
Cl
CH
3
C C
+
CH
3
C H
3
H
CH
3
CH
3
,
Cl
-
)a#t

#ddition Reaction of #l(enes
#ddition Reaction of #l(enes
,3. Hydrogenation
,3. Hydrogenation

5he reaction o& an a'*ene (ith h.+ro)en in

the presence o& cata'.st s-ch as p'atin-m/
nic*e' an+ pa''a+i-m to &orm a'*ane.
C C
,
H
2
-t or .i or -d
C C
H H

;0amples4
,
3.
,
2.
,
H
2
-t /.i / -d
C H
3
C CH
2
CH
3
C H
3
CHCH
3
CH
3
,
H
2
-t /.i / -d

,2.
,2.
Halogenation
Halogenation
of #l(enes
of #l(enes
,i. !n inert sol5ent ,CH
,i. !n inert sol5ent ,CH
2 2
Cl
Cl
2 2
.
.

%'*enes react rapi+'. (ith ch'orine or

bromine in CH
2
C'
2
at room temperat-re to
&orm
!icina' +iha'i+es.
!icina' +iha'i+es.
C C
,
&
2
CH
2
Cl
2
C C
& &

;0ample4
C C CH
3
C H
3
Cl
CH
3
H
Cl
C C CH
3
C H
3
CH
3
H
,
Cl
2
CH
2
Cl
2

=hen bromine is -se+ &or this reaction/ it

can ser!e as a
test &or the presence o&
test &or the presence o&
carbon-carbon +o-b'e bon+s
carbon-carbon +o-b'e bon+s.

"& bromine is a++e+ to a'*ene/ the re++ish

bro(n co'or o& the bromine +isappears
a'most instant'. as 'on) as the a'*ene is
present in e4cess.

Unsaturation test
C C
,
+r
2
CH
2
Cl
2
room t!mp!ratur!
C C
+r +r
9bser!ation2 5he re++ish bro(n bromine +eco'o-rise+

,+.
,+.
Hydrohalogenation
Hydrohalogenation
4 <ar(o5ni(o5's
4 <ar(o5ni(o5's
rule
rule

H.+ro)en ha'i+es (H"/ H>r/ HC' an+ H0) a++ to the

+o-b'e bon+ o& a'*enes to &orm ha'oa'*anes.

5he a++ition o& HA to an

unsymmetrical al(enes
unsymmetrical al(enes,
follo/s
<ar(o5ni(o5's rule
<ar(o5ni(o5's rule.
,
C C
H &
H& C C

<ar(o5ni(o5's
<ar(o5ni(o5's
Rule
Rule
4
4
?
"n the a++ition o& H; to an a'*enes/ the
h.+ro)en
h.+ro)en atom a++s to the carbon atom
o& the +o-b'e bon+ that a'rea+. has the
)reater n-mber o& h.+ro)en atoms.
)reater n-mber o& h.+ro)en atoms.

i. 5he
addition
addition o& H=r to propene/ co-'+
concei!ab'. 'ea+ to either 3
bromopropane or 2bromopropane.
5he main pro+-ct/ ho(e!er/ is 2
bromopropane
C H
2
CHCH
3
,
H+r
C C CH
3
H
H
H +r
H

ii. =hen 2methylpropane reacts (ith H>r/
the main pro+-ct is tertbutyl bromide/
not isobutyl bromide.
5he a++ition o& HA to an unsymmetrical
al(enes/ .ie'+ the main pro+-ct accor+in)
to the <ar(o5ni(o5's rule.
C H
3
C CH
2
CH
3
H+r
,
C H
3
C CH
3
CH
3
+r

CH
3
C
CH
3
CH CH
3

H
+r
CH
3
C
CH
CH
3
CH
3

3
@
Carbocation
, >r
-
#lo,
<echanism
<echanism

CH
3
C
CH
CH
3
CH
3

, >r
-
)a#t
CH
3
C
CH CH
3
CH
3
+r
H

,1. #ddition of H=r to #l(enes in *he
,1. #ddition of H=r to #l(enes in *he


"resence of "ero0ides
"resence of "ero0ides


,#nti <ar(o5ni(o5's rule.
,#nti <ar(o5ni(o5's rule.
=hen a'*enes are treate+ (ith H>r in the presence
o& pero4i+es/ 1991 (e)2 H
2
9
2
) the a++ition occ-rs
in an anti<ar(o5ni(o5 manner
5he h.+ro)en atom o& H>r attache+ to the +o-b'.
bon+e+ carbon (ith &e(er h.+ro)en atoms.

;0ample4
CH
2
CH
2
CH
3
+r
C H
2
CH CH
3
H+r
0OO0
,

CH
2
C CH
2
C H
3
CH
3
,
H+r
H
2
O
2
Complete the follo/ing reactions4
Complete the follo/ing reactions4
,3.
,2.
CH
2
H+r
H
2
O
2
,

,ii.
,ii.
!n a7ueous ,
!n a7ueous ,
Halohydrin
Halohydrin
Formation.
Formation.

"& the ha'o)enation o& an a'*ene is carrie+

o-t in aA-eo-s so'-tion/ the ma3or pro+-ct
o& the o!era'' reaction is a ha'oa'coho'
ca''e+ a
ha'oh.+rin.
ha'oh.+rin.
C C
,
&
2 ,
H
2
O C C
& OH
&
2
= Cl or +r
(alo(1drin

E4amp'e2

"& the a'*enes is

-ns.mmetrica'
-ns.mmetrica'/ the
ha'o)en
ha'o)en en+s -p on the carbon atom (ith
the
)reater n-mber o& h.+ro)en atoms.
)reater n-mber o& h.+ro)en atoms.
C C
H
H H
H
,
+r
2 ,
H
2
O C C H H
H
+r OH
H
2-bromob-tano'

#nsat-rate+ test
9bser!ation 2 the re++ish bro(n bromine +eco'o-rise+

;0ample4
C H
3
C CH
2
CH
3
,
+r
2 ,
H
2
O
1-bromo-2-meth.'-2-propane
C C H C H
3
CH
3
OH +r
H

Complete the follo/ing reaction2
CH
3
,
+r
2
,
H
2
O

,-. Hydration of #l(ene
,-. Hydration of #l(ene

5he aci+-cata'.6e+ a++ition o& (ater to the

+o-b'e bon+ o& an a'*ene (h.+ration o& an
a'*ene) is a metho+ &or the preparation o&
'o( mo'ec-'ar (ei)ht a'coho's.

5he aci+ most common'. -se+ to cata'.se

the h.+ration o& a'*enes are +i'-te so'-tion
o& s-'ph-ric aci+ an+ phosphoric aci+.

5he a++ition o& (ater

5he a++ition o& (ater to the +o-b'e bon+
&o''o(s <ar(o5ni(o5's rule.
C C
,
H
2
O
H
3
O

C C
H OH

;0ample4
C H
3
C CH
2
CH
3
H
2
O
H
3
O

,
C CH
3
C H
3
OH
CH
3


Complete the follo/ing reactions4
Complete the follo/ing reactions4
,3.
,3.
CH
2
H
2
O
H
3
O

,
,2.
C H
2
CH CH
3
H
2
O
H
3
O

,

Bechanism
..
CH
3
C
CH CH
3
CH
3
H
O
H
H

CH
3
C
CH
3
CH
CH
3
H

S5E$ 1

..
.
. CH
3
C
CH
3
CH
CH
3
H

H
2O
S5E$ 2
CH
3
C
CH
3
CH
CH
3
H
O
H
H
.
.

S5E$ 3
CH
3
C
CH
3
CH
CH
3
H
O
H
H
.
.
H
2
9
..
.
.
CH
3
C CH CH
3
CH
3
OH
H

H
3O

..

,6.
,6.
#ddition of 8ulphuric #cid to
#ddition of 8ulphuric #cid to
#l(enes
#l(enes

%'*enes +isso'!e in concentrate+ s-'ph-ric

aci+ to &orm
a'*.' h.+ro)en s-'phates
a'*.' h.+ro)en s-'phates.

%'*.' h.+ro)en s-'phates can be easi'.

h.+ro'.se+ to a'coho's b. heatin) them
(ith (ater.

5he o!era'' res-'t o& the a++ition o&

s-'ph-ric aci+ to a'*enes &o''o(e+ b.
h.+ro'.sis is the Bar*o!ni*o! a++ition o&
H an+ -9H.

C C
C H
3
C H
3
CH
3
CH
3
conc. H
2
SO
4
C C CH
3
C H
3
CH
3
H OSO
3
H
CH
3
al%1l (1dro"!n #ulp(at!
H
2
O
(!at
C C CH
3
C H
3
CH
3
H OH
CH
3

;0ample4
C H
2
CH CH
3
conc.H
2
SO
4
C H
3
CH CH
2
OSO
3
H
H
H
2
O
(!at
C H
3
CH CH
2
OH
H

#l(enes undergo a number of reactions

in /hich the C=C is o0idized
B . 90idation of #l(enes
B . 90idation of #l(enes
8Bn9
4
o6ono'.sis

basic/co'+/+i'-te

aci+ic/hot/concentrate+

i.
i.
)ith
)ith
cold
cold
and
and
dilute
dilute
potassium
potassium
permanganate, C<n9
permanganate, C<n9
1 1

$otassi-m perman)anate in a'*a'ine

so'-tion can be -se+ to o4i+ise a'*enes
to 1/2-+io's ()'.co's).

C C
,
'2nO
4
(purpl!)
OH
3
4cold
C C
OH OH
,
2nO
2
($ro,n pr!cipitat!)
9bser!ation2 $-rp'e co'o-r o& 8Bn9
4
+eco'o-rise+ an+
bro(n precipitate &orme+.

5his reaction is ca''e+

=aeyer's
=aeyer's
test
test.

"t is a
test &or the presence o& C=C
test &or the presence o& C=C (here
the p-rp'e co'o-r o& the 8Bn9
4

+eco'o-rise+/ an+ bro(n precipitate o&
Bn9
2
is &orme+.

;0ample4
C H
2
CH
2 ,
'2nO
4
cold
OH
3
4H
2
O
C C H H
OH
H H
OH
,
2nO
2

ii. )ith
hot
hot potassium permanganate
solutions to al(enes

=hen o4i+ation o& the a'*ene is carrie+ o-t

in
aci+ic so'-tion o& 8Bn9
aci+ic so'-tion o& 8Bn9
4 4
/ c'ea!a)e o& the
+o-b'e bon+ occ-rs an+ carbon.'-containin)
pro+-cts are obtaine+.

C
O
CH
3
C H
3
,
C
O
CH
3
C H
3
C C CH
3
C H
3
CH
3
CH
3
,
'2nO
4
(ii) H
3
O

(i) OH
3
4(!at
!f the double bond is
tetrasubstituted
tetrasubstituted, the
t/o carbonylcontaining products are
(etones
(etones

!f
a hydrogen is present at double
a hydrogen is present at double
bond
bond, one of the carbonylcontaining
products is a
carbo0ylic acid
carbo0ylic acidD

!f
t/o hydrogens are present on one
t/o hydrogens are present on one
carbon
carbon,
C9
C9
2 2
is formed.

2.
C H
2
CH CH
3
,
'2nO
4
(i) OH
3
4(!at
(ii) H
3
O

C
O
CH
3
HO
,
CO
2
,
H
2
O

*he o0idati5e clea5age of al(enes can

be used to
establish the location of the
establish the location of the
double bond
double bond in an un(no/n al(ene.

;0ample4

%n -n*no(n a'*ene (ith the &orm-'a

C
C
7 7
H
H
14 14

-n+er)oes o4i+ation (ith hot basic
potasi-m perman)anate so'-tion to &orm
propanoic aci+
propanoic aci+ an+
b-tanoic aci+.
b-tanoic aci+. =hat is
the str-ct-re o& this a'*eneC

C
7
H
14
,
'2nO
4
(i) OH
3
4(!at
(ii) H
3
O

C
O
OH CH
2
C H
3
,
C
O
OH
CH
2
CH
2
C H
3

#ns/er4
C
O
OH
OH CH
2
C H
3
C
O
OH
OH CH
2
CH
2
C H
3
propanoic acid
$utanoic acid
CH
2
CH
2
CH
3
C C CH
2
C H
3
H H
33(!pt!n!

Example
Example

%n -n*no(n a'*ene -n+er)oes o4i+ation

in hot basic 8Bn9
4
&o''o(e+ b. aci+i&ic to
)i!e the &o''o(in) pro+-ct2

CH
3
CCH
2
CH
2
CH
2
CH
2
C 9H
De+-ce the str-ct-ra' &orm-'a &or the
-n*no(n a'*ene.
9
9

iii. 9zonolysis of #l(enes

% more (i+e'. -se+ metho+ &or 'ocatin)

the +o-b'e bon+ o& an a'*ene is the -se
o& o6one (9
3
).

96one reacts !i)oro-s'. (ith a'*enes to

&orm -nstab'e compo-n+s ca''e+
mo'o6oni+es
mo'o6oni+es/ (hich rearran)e
spontaneo-s'. to &orm compo-n+s
ca''e+
ozonides
ozonides
.
.

C C
,
O
3

C C
O
o5onid!
O
O

9zonides4
9zonides4

5ery unstable compounds

can easily e0plode 5iolently

they are not usually isolated but are

reduced directly by treatment /ith
/ater and in the presence of zinc and
acid ,normally acetic acid. to gi5e
carbonyl compounds ,either
aldehydes or (etones..

o5onid!
C C
O
O
O
,
6n
H
2
O4H

H
1

C = O

,
O = C
1
H

;0ample4
C CH C H
3
CH
3
CH
3
(i) O
3
(ii) 6n4H
2
O/H

C
O
CH
3
C H
3
C
O
CH
3
H
,

3. )rite the structure of al(ene that
/ould produce the follo/ing products
/hen treated /ith ozone follo/ed by
/ater, zinc and acid
CH
+
C9CH
+
and CH
+
CH,CH
+
.CH9
;0ercise
;0ercise

Example
Example

De+-ce the str-ct-ra' &orm-'a o& an

a'*ene that )i!es the &o''o(in) compo-n+
(hen it reacts (ith o6one in the presence
o& En F H
,
.
9=CH-CH
2
-CH
2
-CH(CH
3
)CH=9

2. #cidcatalyzed dehydration of
neopentyl alcohol, ,CH
+
.
+
CCH
2
9H,
yields 2methyl2butene as the ma:or
product. 9utline a mechanism
sho/ing all steps in its formation.

Exercise
Exercise

Compo-n+s %/ >/ C an+ D are isomers

(ith the mo'ec-'ar &orm-'a C
4
H
G
.
%
% an+
>
>
)i!e a
positi!e >ae.er test
positi!e >ae.er test/ (hi'e C an+ D
+o not.
%
%

e4ists as
cis- an+ trans- isomers
cis- an+ trans- isomers/
(hi'e > +oes not ha!e )eometrica'
isomers.
C has on'. secon+ar. h.+ro)en
C has on'. secon+ar. h.+ro)en/
(hi'e
D has primar./ secon+ar. an+
D has primar./ secon+ar. an+
tertiar. h.+ro)en
tertiar. h.+ro)en. i!e the "#$%C names
&or %/ >/ C/ an+ D.