Organic Chemistry

Topic 10.1.1 – 10.1.8

1 2 3 4 bonds
HONC
What is organic chemistry?
• study of carbon, the compounds it makes, and
the reactions it undergoes
• over 16 million carbon-containing compounds
are known
• because the C-C single bond (348 kJ mol-1) and
the C-H bond (412 kJ mol-1) are strong, carbon
compounds are stable
• carbon can form chains and rings
Homologous series/compounds (10.1.1)

• related compounds that have the same

functional group (groups of atoms found within
molecules that are involved in the chemical reactions
characteristic of those molecules)
• differ from each other by a CH2 unit
• can be represented by a general formula
– examples:
• CnH2n+2 (alkanes) or CnH2n (alkenes) or…
• 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 increase Alkane Formula Boiling
Pt./oC
with more carbon
atoms
methane CH4 -162.0
• Why?
– intermolecular
forces increase
ethane C2H6 -88.6
– adding a CH2 adds
more electrons propane C3H8 -42.2
• this increases the Van
der Waal’s forces butane C4H10 -0.5
Empirical, molecular & structural formulas (10.1.3)
 Empirical Molecular
• empirical formula Formula Formula
– simplest ratio of
atoms in a CH4 CH4
molecule CH3 C2H6
• molecular formula
CH2O C6H12O6
– actual numbers
of atoms in a CH2 C4H8
molecule
CH2 C8H16
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
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-
2 Eth-
Monkeys
3 Prop- Eat
4 But- Peeled
5 Pent- Bananas
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