Unit 2 Mod 1 Intro to organic chemistry page 1 of 9

Carbon can form vast numbers of organic compounds.

This occurs because of carbon atoms ability to bond to themselves in
long chains. This ability is called catenation. Catenation occurs
because of the tetravalency of carbon i.e. its valency is ! and carbon
being a small atom" therefore it forms strong bonds #ith itself$
These chains can be straight chains%&

branched chains%&
and rings

Carbon can form ! covalent bonds" but this is not apparent #hen
analysing its electronic configuration of 1s
2
2s
2
2p
2
. 'nly the last 2
electrons are unpaired #hich can be used to form covalent bonds.
(o#ever only T)' covalent bonds can be formed***
Unit 2 Mod 1 Intro to organic chemistry page 2 of 9
In order to form ! covalent bonds" it must have FOUR unpaired
electrons.
'ne of the 2s electrons #ould absorb energy and be promoted to the vacant 2p
orbital to form a ne# EXCITED electronic configuration 1s
2
2s
1
2p
3
* The +
electrons in the 2p subshell and the 1 electron in the 2s orbital are all no#
unpaired" so no# carbon can form ! covalent bonds.
This happens spontaneously since the energy released by forming ! bonds
compensates for the energy absorbed in promoting an electron to a higher
energy level. ,lso the formation of ! bonds is more favourable than forming 2
covalent bonds.
The combination of the usage of the '-. s electron and the T(/.. 0p1
electrons in bond formation results in a hybrid and the process is called
hybridisation.
'rganic compounds are placed in groups called homologous series.
(omologous series have several characteristics
1. ,ll compounds have the same general formula
2. 2ame functional group
+. 2imilar chemical properties
!. 3raduating physical properties as the number of carbon atoms
increases
4. The masses of consecutive members differ by 1! g or by a 5C(
2

group.
, functional group is an atom or a group of atoms responsible for the chemical
properties of a compound
6onds must be first bro7en before a chemical reaction can ta7e place. In
organic chemistry" bonds can be bro7en in t#o #ays.
a$ homolytic fission and b$ heterolytic fission
(omolytic fission %& brea7age of a covalent bond #ith atoms of similar or same
electronegativity resulting in the formation of free radicals. .ach atom retain
one electron from the covalent bond.
-6 8ree radicals are highly reactive species #ith an unpaired electron
(eterolytic fission %& brea7age of a covalent bond #ith atoms of different
electronegativities #ith the formation of a cation and an anion. The more
Unit 2 Mod 1 Intro to organic chemistry page + of 9
electronegative atom retains both electrons from the covalent bond.
Terinolo!y
.lectrophile%& an electron loving species to negatively charged
centres e.g. (
9
" Cl
9
" 6r
9
" I
&
" -'
2
9
-ucleophile%& a nucleus loving species i.e. attracted to positively
charged centres e.g. '(
&
" (
2
'" -(
+
" C-
&
" halide ion
(ydrolysis 5 the splitting of a molecule using #ater or in some cases
the reaction of a molecule #ith #ater as opposed to simple
dissolution
Molecules can be illustrated in several #ays" via epirical for"la"
olec"lar for"la" str"ct"ral or displayed for"la" condensed
for"la or s#eletal for"la.
1. Epirical for"la refers to the simplest #hole number ratio of atoms
in a compound. e.g. C(
2
2. $olec"lar for"la refers to the actual number of atoms in a
compound e.g. C
2
(
!
+. %tr"ct"ral & displayed for"la refers to the diagrammatic
representation of an organic molecule sho#ing the arrangement of atoms
e.g.
!. Condensed for"la refers to the groups of atoms arranged around
each carbon atom in the compound. It does not sho# the arrangement of
the atoms. The condensed formula can be determined from the structural
formula e.g. butane is C
!
(
1:
and the structural formula
Therefore the condensed formula is C(
+
C(
2
C(
2
C(
+
Unit 2 Mod 1 Intro to organic chemistry page ! of 9
4. %#eletal for"la refers to the bare structure of the compound #here
carbon and single hydrogen atoms are not sho#n. It is sho#n by a series
of straight lines and bends. ,n open end represents a 5C(
+
group #hich
a 0bend1 represents a 5C(
2
group. If a double bond is present" the
number of hydrogen atoms #ould decrease appropriately. 'ther
functional groups are sho#n e;plicitly.
butane is sho#n as and butan&2&ol is represented by
Isoeris
There are t#o main types%& structural isomerism and stereoisomerism
2tructural isomerism occurs #hen 2 or more compounds have the same
molecular formulae but their atoms are arranged differently
There are + categories of structural isomerism
a$ chain b$ functional c$ positional
C'(I) I%O$ERI%$
Chain isomers have same molecular formula but differ in the length of
the longest carbon atom chain
.;ample%
2&methylpropane
*O%ITIO) I%O$ERI%
<ositional isomerism is caused by the difference in the position of
functional group in the same chain is termed as position isomerism.
.;ample%
Unit 2 Mod 1 Intro to organic chemistry page 4 of 9
1"2&dichloroben=ene 1"+& dichloroben=ene
O)(+ I%O$ERI%$
8unctional isomers have same molecular formula but different functional
group.

.;ample%
.thyl ,lcohol >imethyl .ther
2tereoisomerism occurs #hen 2 or more compounds have the same
molecular and structural formulae but the atoms are arranged differently
in space
2tereoisomerism can be either a$ geometric ? cis&trans isomerism or
b$ optical isomerism
,eoetric isoeris occ"rs in "nsat"rated copo"nds
)ith the presence of the multiple bond" rotation about the C@C bond is
difficult #ithout brea7ing the bonds bet#een them
.;ample
6oth a$ and b$ have the molecular formula C(ClC(Cl but the atoms
are arranged differently in space
In a$ similar atoms either the Cl or the ( are on O**O%ITE sides of
T'E DOU-+E -O)D. This configuration is called 0trans1. )hile in
b$ similar atoms are on the %($E side of T'E DOU-+E -O)D" this
configuration is called 0cis1
Unit 2 Mod 1 Intro to organic chemistry page A of 9
2o compound a$ is trans&1"2&dichloroethene and
compound b$ is cis&1"2&dichloroethene
Optical isoeris occurs #hen there is no syetry about a carbon
atom in a compound
8or e;ample Imagine a carbon atom #ith four different atoms or groups
of atoms attached to it
There is no line of symmetry one can dra# for this molecule
Therefore the molecule is asymmetric. 2ince there is no line of
symmetry about the central carbon atom" that carbon atom is said to be
C'IR(+.
Mirror images of compounds #ith chiral carbon atoms are said to be
non.s"periposable. Thin7 of trying to fit your left hand directly on top
of your right hand. Bou #ould realise that they dont fit neatly on each
other.
$irror ia!es of copo"nds /ith chiral carbon atos are called
enantioers0 The dotted line represents the irror line0
<lease note the diagram sho#s a +
dimensional arrangement. The
0/ed!e1 sho#s the bond coming
out of the plane of the paper
to/ards the observer and the
dotted line sho#s the bond
coming out of the plane of the
paper a#ay from the observer.
Unit 2 Mod 1 Intro to organic chemistry page C of 9

)ote 1hen sho/in! chiral carbon atos they $U%T be indicated
/ith an asteri2 ne2t to it0 345
.nantiomers are identical in every #ay in terms of chemical and physical
properties EXCE*T that one rotates plane polarised light to the left and
the other rotates plane polarised light to the right by the sae de!ree.
If there are eDual concentrations of both enantiomers in a mi;ture" there
#ould be no observed optical activity and the mi;ture #ould called a
raceic i2t"re or a raceatate.
'ne final concept to understand is that some atoms or groups of atoms
are electron #ithdra#ing pull electrons to#ards themselves$ and others
are electron donating push electrons a#ay from themselves$. ,toms or
groups of atoms #ith electronegative atoms are electron #ithdra#ing and
thus have a negative inductive effect &I$" #hile the others li7e al7yl
groups are electron donating and have a positive inductive effect 9I$.
Mesomeric effect is the same as the inductive effect but it occurs in
multiple bonds, while inductive effect occurs in single bonds.
1or#sheet on intro to or!anic cheistry
)rite your ans#ers on the spaces provided or circle the most suitable
letter
1. )hat is tetravalencyE
FFFFFFFFFFFFFFFFFFFFFFFFFFF
2. (o# many str"ct"ral isomers have the molecular formula C
!
(
1:
E
a$ 1 b$ 2 c$ + !$
+.
a$ >ra# the fully displayed formula corresponding to C(
2
ClC(ClC(
+
Unit 2 Mod 1 Intro to organic chemistry page G of 9
b$ 'n the fully displayed formula you dre# above" indicate the chiral
carbon atom #ith an asteri;.
c$ >ra# the t#o enantiomers resulting from the chiral carbon atom you
indicated above in part b$
!. Using this condensed molecular formulae C(
2
ClC(
2
C(
+
)hich type of structural isomerism can it e;hibitE
FFFFFFFFFF.FFFFFFF
4 i$. )hich compounds #ould e;hibit optical isomerismE
a$ C(
!
b$ C
2
(
A
c$ C(
+
C(Cl6r d$ C(
+
C(
2
Cl
ii$ >ra# the optical isomers for the compound you have chosen in 4 i$
A. 6ut&2&ene is said to sho# 0stereoisomerism1. >ra# the cis and trans
isomers of but&2&ene
C.
Unit 2 Mod 1 Intro to organic chemistry page 9 of 9