ORGANIC

COMPOUNDS

Alkanes,
Alkenes,
Alkynes and
Cyclic Compounds
 Carbon has 4 valence
Study of molecular electrons so it is capable
carbon compounds of making 4 covalent
bonds

ORGANIC Carbon atoms can form Chains can be straight,

CHEMISTRY chains of any length branched or cyclic

Chains can include

Many different atoms
single, double or triple
can bond to carbon
bonds
 ORGANIC CHEMISTRY
• Study of molecular carbon compounds
• Carbon has 4 valence electrons so it is capable of making 4
covalent bonds
• Carbon atoms can form chains of any length
• Chains can be straight, branched or cyclic
• Chains can include single, double or triple bonds
• Many different atoms can bond to carbon
• Carbon is a non-metallic element
• Its name derives from Latin “carbos”
meaning charcoal
• Found in reserves of coal, oil and
natural gas as well as in all living
matter
• In its pure form, it occurs in three
allotropic forms:
• amorphous (eg. black carbon/ soot)
• graphite
• diamond
 ORGANIC COMPOUNDS CAN BE
CLASSIFIED AS BEING:

Aliphatic Aromatic
• organic compounds in which • organic compounds that
the carbon atoms are arranged contain a benzene ring.
in a straight or branched chain
 ALIPHATIC
HYDROCARBONS
• Compounds in these families form a
homologous series – each member of the
family differs from every other member
by a fixed repeating group (ie each
homolog has a CH2 unit more than the
preceding member)
Family ALKANES ALKENES ALKYNES
Type of bonds only single-bonded at least one carbon- at least one carbon-
carbon atoms carbon double bond carbon triple bond in
in each molecule each molecule

Saturated or SATURATED since UNSATURATED UNSATURATED

unsaturated they contain the since they do NOT since they do NOT
maximum number of contain the contain the maximum
bonded atoms maximum number of number of bonded
bonded atoms atoms

General formula CnH2n+2 CnH2n CnH2n-2

Reactivity Generally unreactive they are much more they are much more
reactive since there reactive since the
is room for more triple bond is even
bonds less stable than a
double bond
Alkyl groups
 If one hydrogen is removed from
each member of the alkane series, a
neutral radical with one unpaired
electron is formed.
 A dash is included to represent that it
does not form a complete molecule -
it must be bonded to another
molecule.
 These radicals form branches off of
straight chain molecules.
 They are named using a prefix to
indicate the number of carbon atoms,
and the suffix “YL”.
Note: some alkyl groups have different possible arrangements are assigned common
names to distinguish them.

• Eg. propyl

iso-propyl
 

butyl

sec-butyl

iso-butyl

tert-butyl
 
DRAWING ORGANIC COMPOUNDS
There are an infinite number of possible organic structures.
There are several methods of conveying these structures.

Simply indicates the type and C4H10

Molecular Formula
number of atoms of each
element in the compound

Shows bonding between all

Complete
atoms found in the compound
Structural Formula NOTE: Structural Formula
omits the hydrogens, their
location is implied by a dash.

Shows bonding between carbon CH3CH2CH2CH3

Condensed Formula
atoms in the compound

Uses points to represent carbon

Skeleton formula
atoms, hydrogen atoms are
inferred
• The different representations are necessary since several organic
compounds may have the same molecular formula but different
structural formulas. These are referred to as ISOMERS.
 

• We can distinguish between isomers by giving each compound a

unique name. These names are determined using the rules outlined
by IUPAC, the International Union of Pure and Applied
Chemistry.
complete

condensed

line
How many different isomers of C5H12 can be formed?
 CYCLOALKANES
• Hydrocarbons whose molecules have a closed ring structure.
These molecules are isomers of the alkene family.
• These structures can form branches of a longer straight chain. If
this occurs, they are named as alkyl groups. (eg. cycloproprane
vs. cyclopropyl).
• Often these structures are represented by their skeleton formula.
 NAMING ORGANIC COMPOUNDS
• The name of any organic compound
is comprised of three portions:
PREFIX + ROOT + SUFFIX
• The root name of the compound is
determined from the number of C
atoms in the longest continuous chain.
• The suffix indicates the type of
organic compound (FAMILY) and is
placed after the root.
• The prefix identifies any groups
attached to the main chain.
 IUPAC NOMENCLATURE RULES FOR
ORGANIC COMPOUNDS
1. Identify the longest carbon chain, called the
PARENT CHAIN. This may be a straight chain
or a cyclic structure.
 
2. The number of carbon atoms in the parent
chain is indicated by the first part, root, of the
parent name.
 
3. A suffix is used to indicate whether there
are single (ANE), double (ENE), or triple
(YNE) bonds present.
4. Number the parent chain from the end so that the substituents are attached to the
carbon atom with the lowest possible number (first point of difference rule). If there
are two or more groups and the numbering is a tie, the group that comes first
alphabetically gets the lowest number.
Some non-carbon side groups that you might encounter are:
  
 Br- bromo Cl- chloro I- iodo F- fluoro

NO2 - nitro NH2 – amino OH – hydroxy

5. If the same substituent is present more than once, use a prefix to indicate this (di,tri,
tetra, penta, hexa…) and include a number to indicate each substituent’s location.
 
 
6. When writing the final name, list substituents in alphabetical order, ignoring any
prefixes. Separate words by hyphens; separate numbers by commas, there are no spaces
between letters.
 
DRAWING ORGANIC COMPOUNDS

To draw a structure when you are given the name of an alkane,

1. Draw the parent chain or carbon ring from the last part of the
compound name.
2. Identify the carbon atoms where each of the substituents is
attached.
3. Draw the substituents attached to the parent chain or ring.
 EXAMPLES:

a) 4-ethyl-3,5-dimethylnonane
 EXAMPLES:

b) 7-ethyl-2-methyl-4-iso-propyldecane
 EXAMPLES:

c) 1-ethyl-2-propylcyclobutane
HW p. 17 - #1-5
1.2 ALKENES AND ALKYNES
To name compounds that contain a multiple bond, many of the same rules
apply with the following additions.
1. Identify the parent chain or ring that contains the multiple
bond. If the chain or ring contains a double bond, it is an
alkene, if it contains a triple bond, it is an alkyne.

2. If the hydrocarbon chain has more than one double or triple

bond, add a prefix to indicate the number of multiple bonds.

3. Number the parent chain or ring so that the first carbon

atom involved in a multiple bond has the lowest possible
number. Write this number before the suffix. (only necessary
if there are more than 3 carbon atoms. NOTE: When
numbering a ring, be sure to number across the multiple bond
(ie the bond must occur between carbon 1 and 2)
4. Number and name any substituents using the first point of
difference and alphabetization rules.

5. The letter a is omitted from the prefixes when followed by a

vowel.

6. When both a double and a triple bond are present, the chain is
numbered and then the suffixes are listed in alphabetical order.
EXAMPLES
DRAW THE FOLLOWING MOLECULES:

a) 7-bromooct-3-yne
DRAW THE FOLLOWING MOLECULES:

b) 2-methylpenta-1,4-diene
DRAW THE FOLLOWING MOLECULES:

c) 4,5-dimethylcyclohept-2-yne
 
1.3 AROMATIC HYDROCARBONS
 AROMATIC COMPOUNDS
These compounds all contain a benzene ring.

The benzene ring has a molecular formula C6H6. Friedrich Kekule

proposed a hexagonal arrangement of carbon atoms with alternating
double bonds.

https://www.youtube.com/watch?v=2NRwd-JJFm4
• This is not completely accurate, though, since benzene does NOT
react in the same manner as the alkene family.
• The unusual stability of benzene was explained by the theory of
resonance.
• . Because of this, it is often represented by a hexagon with a circle
in the centre to represent the fact that the bonds in benzene are
delocalized.
 NAMING AROMATIC COMPOUNDS
The benzene ring may be considered the parent chain or it may be
considered the side group

• If an alkyl group is attached to a benzene ring, the compound is

named as an alkylbenzene.
• Alternatively, the benzene ring may be considered as a branch of a
larger molecule, in this case, the benzene ring is called a phenyl
group.
• Alternatively, three common names are often employed to quickly
name common arrangements of benzene containing compounds.
• If more than one alkyl group is attached to a benzene ring, the groups
are numbered using the lowest numbers possible, starting with one of
the added groups. (again, numbering is based on alphabetising).
 DRAWING AROMATIC
COMPOUNDS
• Draw the structural formula of the following compounds
a) 1-fluoro-3-methylbenzene
 DRAWING AROMATIC
COMPOUNDS
• Draw the structural formula of the following compounds
b) 2-phenylbut-2-ene
• The chemical 2,2-bis(4-hydroxyphenyl) propane, more
commonly known as Bisphenol A (BPA), is a chemical
monomer used primarily in the production of polycarbonate
BPA
plastic and epoxy resins.
 Polycarbonate is used in food contact
materials such as beverage bottles BPA
• infant feeding bottles,
• food containers,
• processing equipment
• and other articles.

Epoxy resins are used in protective linings

for variety of canned foods and beverages,
including infant formula.
Health Canada's Food Directorate has concluded that
the current dietary
exposure to BPA through food packaging uses is not
expected to pose a health risk to the general population,
including newborns and infants.
• HW: p. 31 #1,2