Alkanes

Module 7 - Organic Chemistry
Nomenclature
Inquiry question: How do we systematically name organic chemical compounds?
Students:
• investigate the nomenclature of organic chemicals, up to C8, using IUPAC conventions, including simple
methyl and ethyl branched chains, including:
– alkanes
– alkenes
– alkynes
– alcohols (primary, secondary and tertiary)
– aldehydes and ketones
– carboxylic acids
– amines and amides
– halogenated organic compounds
Organic chemistry = carbon - based compounds
Carbon Bonding
Carbon = 1s22s22p2 = four valence electrons
- carbon atom can form four covalent bonds with up to four other carbon atoms
- long, branched chains and even rings of carbon can form
- carbon atom can form four covalent bonds with up to four other non-metal atoms (hydrogen,
oxygen, nitrogen, sulfur, phosphorus and halogens)
- single, double or triple bonds can be formed between carbon atoms
- these factors create a wide variety of carbon compounds

Organic chemistry = carbon - based compounds
Carbon Bonding
methane ammonia ethene CO2 ethene ethyne

Carbon Bonding
- C≡C, C=C and C−C bonds are strong
- other elements lack bond strength of carbon

(Si−Si, O−O)
- H−H is strong but lacks number of bonds
- Si−Si has bond number but lacks strength
- carbon therefore able to form long, robust frames

for large molecules
Representing Organic Molecules
- molecular formulae
- structural formulae
- condensed structural formulae
Molecular formulae
- C2H6O and C4H8O2 indicate number and type of atoms of each element present
- they do not indicate how the atoms are arranged
Structural formulae
- show spatial location of atoms relative to one another in a molecule
- show number and location of covalent bonds
- lone pair electrons are omitted for convenience

Structural formulae
- VSEPR theory = electron pairs repel each other therefore bonds are at an angle 109.5° (tetrahedral)
- The structure of methane is described as a tetrahedral shape because the four single bonds are pointing to the
corners of a tetrahedron
- tetrahedral distribution of bonds = zig-zag shape

Condensed structural formulae
- indicate connections without 3D arrangement of atoms
- the carbon chain is represented on one line of text Molecular formula = C9H20 IUPAC Name = 3-ethyl-2-methylhexane
- carbon atoms and all the atoms attached to them are listed
in the order that they appear in the structural formula
- single bonds are not shown but double and triple carbon-
carbon bonds are often shown
- groups of atoms that form branches in a molecule are

written in parentheses after the carbon atom to which they
are attached
Inquiry question: How do we systematically name organic chemical compounds?
Students:
• investigate the nomenclature of organic chemicals, up to C8, using IUPAC conventions, including simple methyl
and ethyl branched chains, including:
– alkanes
– alkenes
– alkynes
Hydrocarbons
Alkanes
Alkanes
- general formula CnH2n+2
- only single bonds
- carbon atoms are saturated (cannot bond with any more atoms)
- alkanes are a ‘homologous series’ (group of compounds with same general formula)
- homologous series molecules increase in length by CH2
- members of the same homologous series have:
- similar structures
- similar chemical properties
- the same general formula
- a pattern to their physical properties.

IUPAC Naming Simple of Alkanes
- the prefix of the name refers to the number of carbon atoms
- all end in '-ane' to indicate that the carbon-carbon bonds are all single bonds
IUPAC Naming Branched Alkanes
- Isomers = molecules with same number and type of atoms but arranged in different ways
- methane, ethane, propane = no chain isomers
- from butane, chain isomers are possible
- branches (side chains) containing only C and H are ‘alkyl’ groups
- prefix = number of carbon atoms in the side chain
- suffix = 'yl'
IUPAC Naming Branched Alkanes
- Identify the parent name or stem name by finding the longest continuous chain of carbon atoms
- Place name of each alkyl group before the parent molecule name
- More than one type of alkyl group = list the groups in alphabetical order
- More than one of the same type of alkyl group = use prefix 'di', 'tri’ or ‘tetra’
- Specify the carbon atom to which each alkyl group is attached by a number before the alkyl group
- Choose the direction of numbering to give the smallest possible number to each alkyl group
- Do not include spaces in the name
- Use hyphens to separate numbers from words
- Use commas to separate numbers from other numbers

IUPAC Naming Alkanes and
Condensed Structural Formula
2
1
5
4
IUPAC Naming Alkanes
7
6
10
9
12
11
16
13
15
14
18
17
19
20
• 4-ethyl-3-methyloctane
Draw these alkanes (structural formula)
• 4-ethyloctane • 2-methylpentane
• 3-ethyl-2-methylpentane • 4-ethyl-2-methylhexane
• 3,3,5-trimethylheptane • 2,2,3,3-tetramethylbutane
• 2-methylbutane • 3-ethyl-2-methylheptane
• 3-ethylpentane • 3-methylpentane
• 2,3-dimethylbutane • 2,2,5-trimethylhexane
Which of these are isomers?

Cycloalkanes
- hydrocarbon that contains carbon atoms joined to form a ring is called a cyclic hydrocarbon
- cycloalkane = all carbon atoms are saturated
- general formula of a cycloalkane is CnH2n
- cyclohexane = C6H12, hexane, C6H14.
- structural formulae rarely show all carbon and hydrogen atoms (line structures represent cycloalkane rings)

Alkanes

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Module 7 - Organic Chemistry

Carbon = 1s22s22p2 = four valence electrons

- long, branched chains and even rings of carbon can form

- single, double or triple bonds can be formed between carbon atoms

- these factors create a wide variety of carbon compounds

methane ammonia ethene CO2 ethene ethyne

- other elements lack bond strength of carbon

- H−H is strong but lacks number of bonds

- Si−Si has bond number but lacks strength

- carbon therefore able to form long, robust frames

- they do not indicate how the atoms are arranged

- show spatial location of atoms relative to one another in a molecule

- show number and location of covalent bonds

- lone pair electrons are omitted for convenience

- tetrahedral distribution of bonds = zig-zag shape

Condensed structural formulae

- indicate connections without 3D arrangement of atoms

- groups of atoms that form branches in a molecule are

- general formula CnH2n+2

- only single bonds

- homologous series molecules increase in length by CH2

- members of the same homologous series have:

- similar chemical properties

- the same general formula

- a pattern to their physical properties.

- the prefix of the name refers to the number of carbon atoms

- methane, ethane, propane = no chain isomers

- from butane, chain isomers are possible

- branches (side chains) containing only C and H are ‘alkyl’ groups

- prefix = number of carbon atoms in the side chain

- Do not include spaces in the name

- Use hyphens to separate numbers from words

- Use commas to separate numbers from other numbers

Which of these are isomers?

- cycloalkane = all carbon atoms are saturated

- general formula of a cycloalkane is CnH2n

- cyclohexane = C6H12, hexane, C6H14.

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