Organic Compounds - Alkanes

Dr. Sean Bonness

Chemistry Department
El Camino College

Organic compounds
• All contain carbon.
• Organic chemistry is the study of
carbon containing compounds.
• The essential needs of daily human
life are food, fuel, shelter, and
clothing - all are organic in nature,
except water (H2O).

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 Bonding characteristics and Isomerism

• What is the electronic configuration of

Carbon

• Mixing of the 2s and 2p orbitals for carbon

produce sp3 hybrid orbitals

• The hybrid orbitals point towards the

corners of a regular tetrahedron. For
example methane (CH4).

Bonding characteristics and Isomerism

(Cont.)
• Carbon atoms bond covalently to other carbon
atoms to form chains or networks.

• A third carbon can join the end of this chain.

• The process can continue to form chains of almost

any length.

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 Bonding characteristics and Isomerism
(Cont.)
• Carbon can also share more than on pair of
electrons to form multiple bonds

• Structural Isomers - compounds that have the

same molecular formula but in which the atoms
bond in different patterns.
• For example, what are the isomers for the
compound with molecular formula C4H10?

Bonding characteristics and Isomerism

(Cont.)
• What are the structural isomers of C2H6O?

• Structural isomers exert a significant influence

on properties. Ethyl alcohol is a liquid at room
temp., whereas dimethyl ether is a gas.
• What is a structural isomer of C3H6O?

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 Functional groups

class Functional Expanded Condensed Name

group structure structure

Alkane

Alkene

Alkyne

Functional groups (cont.)

class Functional Expanded Condensed Name

group structure structure

Aromatic

Alcohol

Ether

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 Functional groups (cont.)

class Functional Expanded Condensed Name

group structure structure

Amine

Aldehyde

Ketone

Functional groups (cont.)

class Functional Expanded Condensed Name

group structure structure

Carboxylic
Acid

Ester

Amide

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 Functional Groups (cont.)

• Write condensed structural formulas for the

following compounds.

Alkane structures

• Hydrocarbons - simplest of all organic compounds. Only

contain Carbon and Hydrogen.
• Are called Saturated Hydrocarbons.
• Unsaturated hydrocarbons have double and triple bonds.
Which of the functional groups are unsaturated?

• We also have normal alkanes and branched alkanes, i.e.

butane.

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 Conformations of alkanes

• Conformations are the different arrangements of atoms

in space achieved by rotation about a single bond.
• Butane

• Ethane

• Are these pairs structural isomers?

Alkane Nomenclature

• Assigning IUPAC names.

• Step 1 - name longest chain.

• Step 2 - number the longest chain

• Step 3 - locate and name attached alkyl groups.

• Step 4 - combine longest chain and alkyl groups into

name

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 Alkane Nomenclature (cont.)

• Step 5 - indicate the number and position of

attached alkyl groups. If two or more alkyl
groups, then use prefixes di, tri, tetra, etc.

Common names

• Some chain alkanes have a common name. Rarely

used for alkanes having more than five carbon
atoms.
• Some widely used common names are:

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 Cycloalkanes

• For alkanes the structural formula is CnH2n+2

• Is C3H6 an alkane?
• If form a ring than

• And has the structural formula

Cycloalkanes

Name Structural formula Condensed formula

cyclopropane

cyclobutane

cyclopentane

cyclohexane

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 Shapes of cycloalkanes

• Stereoisomers are compounds with the same

structural formula but different spatial
arrangements of atoms.
• For example 1,2-dimethylcyclopentane

• Geometric isomers are stereoisomers in which

the geometry of their groups are maintained by
rings and are called cis-trans isomers.

Shapes of cycloalkanes (cont.)

• Show geometric isomers for 1,2-

dimethylcyclobutane

• What are the geometric isomers for 1,3-

difluorocyclobutane?

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 Shapes of cycloalkanes (cont.)

• Cyclohexane ring is not flat.

• In standard conformation, lower right hand carbon is

designated C-1.
• All other carbons are numbered clockwise.
• If atom or group bonded at C-1, then it is in the
equatorial position. More stable than axial position.

Shapes of cycloalkanes (cont.)

• For most stable conformation of disubstituted

cyclohexane
– Place one substituted atome or group at C-1 in the
equatorial position.
– Place the second atom or group cis or trans to the
first atom.

• The most stable conformation for trans-

1,2dichlorocyclohexane is:

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 Physical properties of alkanes

• Alkanes are composed of nonpolar carbon-carbon and

carbon-hydrogen bonds.

• Have lower melting points and boiling points than other

organic compounds due to weak attractions. However as
chain length increases, the dispersion forces increases
and which is why very long chain structures are solids
(see figure 11.18 in S&S text)

Preparation of alkane

• Most common method of preparing an alkane is

adding hydrogen (hydrogenation) to an alkene.
– Example

– The product of the rxn is obtained by adding

a H atom to each C in the double bond and
changing the double bond to a single bond.

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 Combustion of alkane

• Combustion means to burn in air.

• Hydrocarbons burn in air to produce carbon
dioxide and water.
– Example

Halogenation of alkane

• Halogenation is a substitution rxn.

• One H atom of the alkane is replaced by one
halogen atom.
• The mechanism in halogenation of an alkane is
called a free radical mechanism.
• The mechanism has four steps:

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