Organic Chemistry Module

Organic chemistry: the chemistry of carbon compounds which are characterized by covalent bonds. Common
atoms in organic chemistry are:

carbon – carbon can form up to four bonds - these bonds can be single, double or triple bonds:

hydrogen – can form one bond: H−

oxygen – can form up to two bonds – these can be single or double: or

nitrogen – can form up to three bonds – these can be single, double or triple bonds:

- organic compounds are the molecules that make up living things

Organic compounds differ from inorganic compounds in that there are 3 possible formulas for a given compound:

 Empirical Formula (EF) - shows the relative number of atoms making up the compound (simplest ratio)
 Molecular Formula (MF) - shows the number and kind of atoms in the organic compound (actual
formula)
 Structural Formula (SF) - show number, type and arrangement of atoms

Properties of Organic Compounds are governed by a series of carbon atoms linked together to form a stable,
almost completely unreactive backbone to which we add:
• a series of different reactive groups which determine the basic chemistry and identity of the molecule
• when attached to the carbon skeleton, the reactive groups may make the molecule acidic, basic, fishy
smelling , pleasant smelling , explosive! , soluble in water, and so on...

(Note: The carbon backbone contains only carbon and hydrogen atoms.)

Types of Hydrocarbons (molecules that contain carbon and hydrogen):

I. Saturated Hydrocarbons (only single bonds in the backbone)

A. Alkanes - hydrocarbons that contain only single bonds between the carbon atoms in the backbone
- saturated hydrocarbon - all carbon atoms are bonded to four other atoms (hydrogen or carbon)

- general formula: 𝐶𝑛 𝐻2𝑛+2

- name ending: -ane

- most are chain compounds - either straight chain or branched chain

- alkyl groups - formed by removing one hydrogen from the original parent hydrocarbon. By
adding ‘alkyl groups’ (side chains) to the main backbone, we can form complicated
hydrocarbons. These groups cannot exist by themselves - they must be attached
to some molecule.

1
 Saturated Hydrocarbons & Alkyl Groups

Parent Number of C Molecular Alkyl Group

Hydrocarbon atoms Formula
CH4 methane 1 CH4 CH3−
CH3CH3 ethane 2 C2H6 CH3-CH2−
CH3CH2CH3 propane 3 C3H8 CH3-CH2-CH2−
CH3CH2CH2CH3 butane 4 C4H10 CH3-CH2-CH2-CH2−
CH3CH2CH2CH2CH3 pentane 5 C5H12 CH3CH2CH2CH2CH2−
CH3-(CH2)4-CH3 hexane 6 C6H14 CH3-(CH2)4-CH2−
CH3-(CH2)5-CH3 heptane 7 C7H16 CH3-(CH2)5-CH2−
CH3-(CH2)6-CH3 octane 8 C8H18 CH3-(CH2)6-CH2−
CH3-(CH2)7-CH3 nonane 9 C9H20 CH3-(CH2)7-CH2−
CH3-(CH2)8-CH3 decane 10 C10H22 CH3-(CH2)8-CH2−

Note: When there is a chain of two carbon atoms that form a branch off of a backbone, the group is
known as an ‘alkyl group’
- to name the alkyl group, substitute “yl” for the “ane” ending of the original parent chain
Eg. CH3CH3 CH3-CH2−
parent: ethane group: ethyl

The above table is known as a homologous series - a series of compounds whose members differ by the
same structural unit each time. In this case each compound differs by -CH2 from the one before it.

Isomers
Isomers occur when two or more compounds have the same molecular formula.
There are two types of isomers:
1. Structural Isomers - compounds that have the same molecular formula, but occur as differently connected
structures
Example 1: C4H10 (butane) has 2 isomers:

butane isobutane

- butane has a 4-carbon chain

- isobutane has a 3-carbon chain with a methyl group on the middle C
- also called 2-methyl propane

EXERCISE 1: Draw the 3 structural isomers for pentane C5H12. (submit to Portal)

2
 2. Geometric Isomers – are known as cis, trans isomers - involves double bonded carbon compounds
- because of the double bond, the carbons cannot be rotated, resulting in isomers:
Example:

cis-1,2-dibromoethene trans-1,2-dibromoethene
cis - groups are on same side of double bond trans - groups are across the double bond

Nomenclature (naming)
We will be using the IUPAC system (International Union of Pure and Applied Chemistry). The carbon
atoms in the longest chain (backbone) are assigned numbers. The ‘groups’ attached to the main backbone are
then named and their positions identified by the number of the carbon atom on which they are attached.

Rules:

1. The longest chain of carbon atoms determines the parent name of the hydrocarbon:
Example: CH3 - CH2 - CH2 - CH2- CH3 (C6-C5-C4-C3 (C1-C2-C3-C4
| | |
CH2 - CH3 C2-C1) C5-C6)

hexane – the 6 carbon chain is the longest

2. The atoms in the parent chain are numbered consecutively so that the attached groups are indicated by the
lowest possible set of numbers. In the above example, the methyl group (CH3-) is attached to carbon 3,
not carbon 4!!

3. The position of each attached group is indicated by a ‘number’, followed by a ‘dash’, then the name of the
group and finally the name of the parent hydrocarbon.

Examples:

3-ethylheptane

2,2,4-trimethylpentane

- when there are two or more of the same group, we need to use prefixes to show how many
- in the above example, there are three methyl groups = trimethyl
- when there are two or more types of groups, the groups are named alphabetically

Example:
5-ethyl-2,3,7-trimethyloctane

3
4. If the parent chain forms a ring (ie: a cyclic compound) – need to use the prefix: ‘cyclo’

General formula: 𝐶𝑛 𝐻2𝑛

Example:

EXERCISE 2: Draw the following compounds: (submit to Portal #1-3 only)

1. methylcyclohexane

2. 1,2-dimethylcyclobutane

3. 3-cyclopropyl-1-methyl-cyclopentane

Read & Try: Hebden page 218 - 225

4
Properties of Alkanes
 very unreactive - C-C bond and C-H bond are very strong
 methane, ethane, propane & butane are gases at room temperature
 pentane & larger are liquids
 very long chains are solids and are commonly known as waxes & paraffins

EXERCISE #3: Draw full structural formulas for the following: (submit to Portal)

a. 4-ethyloctane b. 2,3-dimethyloctane c. 4-proplynonane

d. 2,3,4,5-tetramethylhexane e. 4,6-diethyl-5-propylnonane

f. propylcyclopropane g. 2-cyclopropylpropane

h. 3,3-diethylpentane i. 2,3,5-trimethyl-4-propylheptane

5
II. Unsaturated Hydrocarbons
If not enough atoms are available to allow each carbon to be bonded to four atoms, we say that the hydrocarbon
is unsaturated. The resulting molecule will have double or triple bonds.

A. Alkenes
- general formula - 𝐶𝑛 𝐻2𝑛 (same as cyclohexanes!)

- contain double bond(s) - made from ‘cracking’ petroleum

- naming: use alkane names, but drop the ‘-ane’ and add ‘-ene’
- the parent name is the longest chain containing the double bond
- the position of the double bond is indicated using the lowest number

Examples: CH3-CH2-C=CH2 1-butene 4 3 2 1

| CH3-C=C-CH3 2-methyl-2-butene
H | |
H CH3

- cis-trans isomerism – when the carbons involved in the double bonds have groups other than H
attached, the position of these groups gives rise to isomers:

H3C CH3 H3C H

\ / \ /
C=C C=C
/ \ / \
H H H CH3

- cis isomer – groups on same - trans isomer – groups on opposite sides of double bond
side of double bond

- aromatics – compounds containing benzene, C6H6 – ring structure

- named the same way as other alkenes, but end in benzene
- these compounds often have fragrance (‘aromatic’)

- see Hebden page 230-232 (You are encouraged to try alkene questions even though it does not need to be submitted)

B. Alkynes
- general formula - 𝑪𝒏 𝑯𝟐𝒏−𝟐

- hydrocarbon containing a triple bond between two carbons -C ≡ C-

- naming: use alkane names, but drop ‘ane’ and add ‘yne’
- the position of the triple bond is indicated using the lowest number

Examples:
H-C≡C-H ethyne (acetylene) CH3-C≡C-CH3 2-butyne

Try: Hebden page 228 & 230 (You are encouraged to try alkyne questions even though it does not need to be submitted)