Organic Chemistry

The study of carbon compounds.

Over 10 million compounds naturally exist
More than 300 000 are synthesized
 Inorganic vs Organic
•– oxides of carboncontaining C H
Hydrocarbons x y
(CO2, CO)

– carbonates,bicarbona
tes (NaHCO3,CaCO3)

– cyanides (NaCN, etc)

– any carbon attached

to a metal and no H
 Origin of organic compounds
• Originally from “organic” meaning life
• Not just chemistry of life, chemistry of carbon

• Naturally occurring organic compounds are found in plants,

animals, and fossil fuels
• All of these rely on the “fixing” of C from CO2

• Synthetic organic compounds are derived from fossil fuels

or plant material
The diversity of carbon compounds is based on
the fact carbon atoms Form 4 Bonds
• Forms strong covalent and nonpolar bonds with itself
and other elements
Review:
• Lewis Structure, Structural formula, Line diagrams
Carbon molecules form complex 3-D shapes

Common Molecular Shapes

• Tetrahedral

• Trigonal planar

• Linear

• Angular

• Trigonal pyramidal
 Simplest Hydrocarbons
Alkanes C C Alkenes C C
H H H H H H H H
H C C C C C H H C C C C C H
H H H H H H H H H H

Alkynes C C Aromatics H
H C H
H H H C C
H C C C C C H C C
H C H
H H H
H
Naming Hydrocarbons
(nomenclature)
 Naming: common vs. IUPAC
• Common names used in the 1800’s are still used for some
compounds today: eg.

H C C H
Commonly known IUPAC: Ethyne
as Acetylene

• The International Union of Pure and Applied

Chemistry (IUPAC) was established in 1900s

• Systematic method allows an infinite number

of compounds to be named given a few rules
Mnemonic for first four prefixes

First four prefixes

• Meth- Monkeys
• Eth- Eat
• Prop- Peeled
• But- Bananas
 Other prefixes

• Pent-

?
Decade
• Oct-
Decimal • Dec-
Decathalon • Hex-, Hept-, Non-
 Alkanes
• Are straight or branched-chain containing
only single bonds
• Are a homologous series –a group of
compounds whose members differ by the
addition of the same structural group
• Named by using prefix and ending -ane
 TASK
• Write chemical and structural formula for all alkanes that
contain up to 10 carbons
• Methane CH4
• Ethane CH3CH3
• Propane CH3CH2CH3
• Butane CH3CH2CH2CH3
• Pentane
• Hexane
• Heptane
• Octane
• Nonane
• Decane
• This is just the beginning…………………………………………………………….. You
may have noticed that branching creates enormous variation
 Try Naming These
CH2 CH2 CH2 CH2 CH3
H3C CH2 CH2 CH2 CH2
 Structural Isomers
• Substances with the same chemical formula
by different arrangements of atoms
• Eg. Butane & 2 methyl-propane

***Isomers have different physical and chemical properties

 TASK: Draw all the isomers for
pentane and hexane
Did you know?
• 3 isomers of pentane
• 5 isomers of hexane
• Heptane-9
• Octane-18
• Nonane-35
• Decane-75
• making a total of 150 different possible alkane
compounds containing 10 carbons.
 Naming Alkanes
• Give the systematic name for the following
alkane:
CH3----CH2----CH----CH3
I
CH3----CH----CH2
I
CH3----CH2
3,4-dimethylheptane
 Task: Writing Condensed
Structural Formulas
• Write the condensed formula for:
a. 3-ethyl-2-methylpentane
b. 3-ethyl-2,3,5-trimethyl heptane
 Greater complexity exists because organic compounds can
form Cyclic (ring) structures?
• Cyclic structures are circular
• Have “cyclo” in name

• Eg. Cyclopropane Cyclopentane

H H
CH2 H C H
H C C H
H2C CH2
C C
H H
H H
 TASK
• Study the following graphic.
• What 2 trends can be
identified?
• Hypothesize why these trends
exist.

• TASK 2: Compare, contrast

and explain the physical
properties of the first 10
alkanes
• have similar chemical properties
• have physical properties that vary in a
regular manner as the number of
carbon atoms increases
– Example: the alkanes
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
 Reactions of Alkanes
• Because they contain C-C and C-h, most
alkanes are relatively unreactive.
• At room temperature, for example, they do
not react with acids, bases or strong
oxidizing agents, and they are not even
attracked by boiling nitric acid.
• Their low chemical reactivty is due
primarily to the strength and lack of polarity
of C-C and C-H bonds.
 Reactions of Alkanes
• They are not completely inert, however.
• One of their most commercially important
reactions is combustion in air, which is the
basis of their use as fuels.
 Background: formulas for HxCy

• CH single bonds Alkanes= CnH2n+2,

• CH with one double bond Alkenes= CnH2n,
• CH with two double bonds Alkynes= CnH2n-2

• Q - How many hydrogens in each of these:

Alkane C6H
Alkene C22H
H3C CH3
 Basic names of hydrocarbons
• Hydrocarbon names are based on:
– 1) class
– 2) # of C,
– 3) side chain type
– 4) position

Q - What names would be given to these:

7C, 9C alkane heptane, nonane
2C, 4C alkyne
ethyne, butyne
1C, 3C alkene
does not exist, propene
 Numbering carbons
Q- draw pentene H H 1-pentene
A- Where’s the bond? H3C C C C C H
5
1 4
2 3 2
4 1
5
We number C atoms H H H H

• Always start numbering for the carbon nearest the double

bond the lowest number

• Q - Name these
H
H3C C C2H4
2-butene C CH3
H
Ethene
H3C CH3 3-nonyne
 Multiple multiple bonds
H3C CH3 2,3-heptadiene

H3C C C C C C C CH2
2,4,6-nonatriyne CH3
• Rules
• Give 1st bond lowest #
• include di, tri, tetra, penta, etc. before ene/yne
• Comma between #s, hyphen between #-letter

H H 2-butyne HC C CH2
H C C C C H H2C CH
H H 1,2,4-pentatriene
CH3CH2CH2CH=C=CH2 1,2-hexadiene
 Cyclic structures
Q- Draw these:

cyclobutene 1,3-cyclopentadiene cyclopropane

H H
H2C CH2 C CH2
H H
C C
HC CH H2C CH2
C C
H H
 Naming side chains CH3

• Names are made up H3C CH3

of: side chains, root

• 2,3-dimethylpentane CH3
• Root is the longest possible HC chain
• Must contain multiple bonds if present
• Add -yl to get name of side chain
H C
3 CH3
CH
• Common side chains include:
*
CH3- methyl CH3CH2- ethyl
CH3CH2CH2- propyl (CH3)2CH- isopropyl
 Naming side chains
Example: use the rules on the bottom of
handout to name the following structure
CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 1: choose the correct ending

ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 2: longest carbon chain

ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 3: attach prefix (according to # of C)

1-hexene
ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 4: Assign numbers to each carbon

1-hexene
 Naming side chains

CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

Rule 4: Assign numbers to each carbon

1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 5: Determine name for side chains
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 6: attach name of branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 7: list alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 8,9: group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 8,9: group similar branches
2-ethyl-4,4-dimethyl-1-hexene
 Try Naming Side Chains

H3C CH2 H3C CH2 CH2 CH3

CH CH3 CH CH CH2 CH3
H2C CH2 H3C CH
CH3
CH3
3-methylhexane
4-ethyl-2,3-dimethylheptane
CH3 CH3 CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
 Naming side chains
Name the structures below
CH3
CH CH2
H3C CH CH3 3-ethyl-2-methylpentane
H2C
CH3

H3C CH3
3-ethyl-1,5,5-
trimethylcyclohexene
CH3
H3C
 Try Drawing These
2,2-dimethyloctane

1,3-dimethylcyclopentane

1,1-diethylcyclohexane

6-ethyl-5-isopropyl-7-methyl-1-octene
Try Naming

CH3 CH3

H3C CH3

CH3 CH3
 Aromatic Hydrocarbons
• Aromatic compounds contain benzene ring
structures and their derivatives.

• Benzene (C6H6)
• most commonly used organic (nonpolar)
solvent
• very stable substance, unreactive
• toxic if inhaled -carcinogenic
• produced by processing coal, crude oil,
gasoline or the combustion of rubber tires

• if it occurs as a side chain it is called a

phenyl group
 Resonance
• The properties of this compound can be explained by following theory:
-the chemical bonds between carbon atoms are not single or double
-all bonds between carbons in the benzene ring are identical in length and
strength
-there is an even distribution of valence electrons around the entire molecule.

• The resonance of the single and double bonds accounts for the stability of
aromatic compounds.
• This is illustrated by resonance structures:
 Aromatic nomenclature H3C

There are 2 naming methods

H3C
1) Numbering carbons
2) ortho, meta, para (stomp) 1,2-dimethylbenzene
orthodimethylbenzene
CH3

ST Ortho Meta
H3C

1,3-dimethylbenzene
H3C Para metadimethylbenzene
H3C CH3

1,4-dimethylbenzene
paradimethylbenzene