Organic Chemistry
Types of Bond & Formula Used in
Organic Compounds
Types of Bond
• Covalent Bond
Types of Formula in Organic
Compounds
• Molecular Formula
• Empirical Formula
• Structural Formula
• Condesed Formula
• Skeletal Formula
Empirical, molecular & structural formulas
(10.1.3)
Empirical Molecula
• empirical Formula r
formula Formula
– simplest ratio CH4 CH4
of atoms in a CH3 C2H6
molecule
• molecular CH2O C6H12O6
formula CH2 C4H8
– actual
numbers of CH2 C8H16
atoms in a
molecule
structural formula
• unambiguously shows how the atoms are
bonded together
• can use condensed structural formulas
– bonds are omitted, repeated groups
put together, side chains put in
brackets
• CH3CH2CH2CH2CH2CH3
– or even CH3(CH2)4CH3
• CH3CH(CH3)CH3
condensed
skeletal formula
– not accepted in the IB for answers but
often used in questions
– every “corner” represents a carbon
– hydrogens are implied
Isomers (10.1.4)
• (structural) isomers: compounds with
the same molecular formula but different
structure (arrangement of atoms)
• different isomers are completely different
compounds
• have different physical properties such as
melting point and boiling point
Structural
Formulas
for C4H10O
Isomers
• have similar chemical properties
• have physical properties that vary
in a regular manner as the number
of carbon atoms increases
– Example: the alkanes
Trends in boiling points of members of
a homologous series (10.1.2)
• melting point and
boiling point Alkane Formul Boiling
increase with more a Pt./ o
C
carbon atoms
• Why?
methan CH4 -162.0
e
– intermolecular
forces increase
ethane C2H6 -88.6
– adding a CH2 adds
more electrons propan C3H8 -42.2
• this increases the e
Van der Waal’s
forces butane C4H10 -0.5
Alkanes
Structural formulas for the isomers of
non-cyclic alkanes up to C6 (10.1.5)
• hydrocarbon chains where all the bonds between
carbons are SINGLE bonds
• CnH2n+2
• draw out and write the structural formulas
for all isomers that can be formed by:
– CH4
– C2H6
– Richard Thornley 10.1.5
C3H8 2:54
– C4H10
– C5H12
– C6H14
Naming the isomers (IUPAC) of non-
cyclic alkanes up to C6 (10.1.6)
1. Richard Thornley 3:35
2. Determine the longest carbon chain
– Use the prefix to denote the number carbons
1 Meth-
Monkeys
2 Eth-
Eat
3 Prop-
Peeled
4 But-
Bananas
5 Pent-
6 Hex-
3. use the suffix “-ane” to indicate that the
substance is an alkane
4. number the carbons in the chain
consecutively, starting at the end closest
to a substituent (groups attached to the
main chain/most busy end)
5. name and number the location of each
substituent
– the name of the substituent will be written before the
main chain and will end with “–yl” (or just memorize the
below)
• CH3 is methyl
• C2H5 is ethyl
• C3H7 is propyl
And with 2 or more side chains:
5. use prefixes di-, tri-, tetra-, to indicate when
there are multiple side chains of the same type
6. use commas to separate numbers and
hyphens to separate numbers or letters.
7. name the side chains in alphabetical order
• How about C5H12? The isomers are:
Pentane 2-methyl-butane 2,2-dimethyl propane
Nomenclature Practice
Name this compound
CH3
H3C1 CH3 9 carbons = nonane
2 3 4 5
6
Cl
7
8
H3C9
Step #1: For a branched hydrocarbon, the longest
continuous chain of carbon atoms gives the root
name for the hydrocarbon
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
Step #2: When alkane groups appear as substituents, they are named
by dropping the -ane and adding -yl.
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
1 9 NOT 9 1
Step #3: The positions of substituent groups are
specified by numbering the longest chain of
carbon atoms sequentially, starting at the end
closest to the branching.
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
2-chloro-3,6-dimethylnonane
Step #4: The location and name of each substituent are
followed by the root alkane name. The substituents
are listed in alphabetical order (irrespective of any
prefix), and the prefixes di-, tri-, etc. are used to
indicate multiple identical substituents.
Alkenes
Structural formulas for the isomers of the
straight chain alkenes up to C6 (10.1.7)
• alkenes have a double bond between two or
more of the carbons
• CnH2n
• draw out and write the structural formulas for all
isomers that can be formed by each
– C2H4
– C3H6 Richard Thornley 10.1.7 (1:37)
– C4H8
– C5H10
– C6H12
Naming the isomers (IUPAC) of straight
chain alkenes up to C6 (10.1.8)
1. suffix changes to “-ene”
2. when there are 4 or more carbon atoms
in a chain, the location of the double
bond is indicated by a number
3. begin counting the carbons closest to
the end with the C=C bond
– numbering the location of the double
bond(s) takes precedence over the
location of any substituents
1-butene 2-butene
but-1-ene but-2-ene
Naming Practice!!!
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
choose the correct ending
ene
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
determine the longest carbon chain with the double bond
ene
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
assign numbers to each carbon
ene
CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
assign numbers to each carbon
ene
CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
attach prefix (according to # of carbons)
1-hexene
ene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
determine name for side chains
1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3
CH3 CH CH CH3
2,4-dimethyl-2-pentene
2,4-dimethyl pent-2-tene
2-butene
CH3 CH3
CH2 CH C CH2 CH3 CH3 C CH CH2
CH3 CH2 CH3
a) 3,3-dimethyl-1-pentene b) same
CH 3
CH 3 C C CH CH CH3
CH3
c) 4,5 dimethyl-2-hexene
