STAGE 2 CHEMISTRY

TOPIC 3: Organic and Biological Chemistry

3.1 - Introduction
Aaron Tieu
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LEARNING OBJECTIVES
• You should be able to:

qDraw extended, condensed and skeletal structural formula of

given organic compounds.

qName simple hydrocarbon molecules

qExplain which molecule has a higher or low melting/boiling point,

and more or less soluble in water/non-polar solvents.
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SCIENCE UNDERSTANDING
Organic compounds can be represented by molecular and structural
formulae.
qDetermine the molecular formula of an organic compound given its
extended, condensed or skeletal structural formula.
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ORGANIC CHEMISTRY
Recall in Stage 1 Chemistry Topic 3.3,

• What is organic chemistry?

• What are some important functional groups?

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EXTENDED STRUCTURAL FORMULA
• Identifies all atoms using chemical symbols as well as showing all
covalent bonds between atoms.

• Branched substituents (e.g. -CH3, -C2H5) and some functional groups

(e.g. –OH, -NH2) are commonly drawn in condensed form. H H
H H H H H
H H H
H C C H
H C C C H
H C C C H H C C O H H H
H H
H H H H C H H H Ethane
H Ethanol
Propane
2-methylpropane
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CONDENSED STRUCTURAL FORMULA
• Shows each carbon atom and its substituents (atoms or groups
bonded to carbon) with no chemical bonds drawn between atoms.
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SKELETAL STRUCTURAL FORMULA
• Shows the bonds between carbon atoms but not the atoms
themselves.

• Hydrogen atoms that are usually attached are removed.

• The bonds between hydrogen and carbon atoms are also removed.

• The carbon and hydrogens are represented in the skeletal structural

formula.

• Each point in a skeletal structure represents a carbon

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SKELETAL STRUCTURAL FORMULA
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SUMMARY
• The comparison between the three different structural formulae.
REVISIT: NAMING SIMPLE 10

HYDROCARBONS
The International Union of Pure and Applied Chemistry (IUPAC) developed a
system to name organic compounds.
ØEnsures each compound has a unique name
Uses the names of the alkanes as a basis.
Name of a compound can consist of three parts:
1. Substituents – any branching or functional group attached to the main
carbon chain.
2. Carbon chain length
3. Chemical ending – denotes what kind of organic compound it is.
REVISIT: NAMING SIMPLE 11

HYDROCARBONS
Carbon atoms Parent name prefix
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-
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ALKYL GROUPS
• Branch from the parent hydrocarbon chain.
• Named based on length of carbon chain. H H H H
• Receives -yl suffix H C C C C H
H H H
Methyl group H C H

-CH3
H
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ALKYL GROUPS
REVISIT: NAMING SIMPLE 14

HYDROCARBONS
• Following rules apply to branched hydrocarbons.
• Rules will be extended to compounds with functional groups.
1. Determine longest carbon chain and name it.
2. Identify alkyl groups.
3. Number carbons in longest chain so that alkyl groups are numbered
as low as possible.
NOTE:
Hyphen (-) is used between number and letter, comma (,) is used between numbers
REVISIT: NAMING SIMPLE 15

HYDROCARBONS
• Following rules apply to branched hydrocarbons.
• Rules will be extended to compounds with functional groups.
4. If two or more identical alkyl groups, use prefixes:

No. alkyl groups 2 3 4 5

Prefix Di Tri Tetra Penta

5. If there are two or more different alkyl groups, name them in

alphabetical order – ignore prefixes for multiple alkyl groups
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EXAMPLE 1
Systematically name the following compound

H H H H H
H C C C C C H
H CH3 H H H
2-methylpentane
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EXAMPLE 2
Systematically name the following compound

H H H H H
H C C C C C H
H CH3 CH3 H H
2,3-dimethylpentane
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EXAMPLE 3
Systematically name the following compound

H H H H H
H C C C C C H
H CH3 CH2 H H
CH3
3-ethyl-2-methylpentane
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EXAMPLE 4
Systematically name the following compound

2-methylbutane
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EXAMPLE 5
Systematically name the following compound

3,3-dimethylhexane
REVISIT: DRAWING SIMPLE 21

HYDROCARBONS
1. Draw the longest carbon chain, based on the parent name.
2. Number the carbons.
3. Attach alkyl groups and/or functional groups.
4. Add hydrogens as needed
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EXAMPLE 1
Draw the organic compound:

2,5-dimethylheptane
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EXAMPLE 2
Draw the organic compound:

3-ethyl-2,2-dimethylhexane
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ALKENES

H H H H H
H C C H H C C C H
H
Ethene Propene
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NAMING ALKENES
• Contain at least one carbon-carbon double bond

ØUnsaturated compound

• Name ends in suffix –ene

• Note:
ØDouble bond must be included in longest carbon chain

ØDouble bond is assigned lowest number when naming

§ Represented in systematic name
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NAMING ALKENES
• If two or more alkene functional groups, use prefixes:

No. double bonds 2 3 4

Prefix Di Tri Tetra

• Prefix is placed immediately before –ene

• E.g. –diene, -triene

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EXAMPLE
Name the following structure:

H H H H
H C C C C C C H
H H H H H H

3-hexene or hex-3-ene
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EXAMPLE
Name the following structure:

H H
H C C C C H
H CH3 H H

2-methyl-1-butene or 2-methylbut-1-ene
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EXAMPLE
Name the following structure:

H H
H C C C C H
CH3 H H H

2-pentene or pent-2-ene
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EXAMPLE
Name the following structure:

H CH3 H
H C C C C H
H CH3 H

2,3-dimethyl-2-butene or 2,3-dimethylbut-2-ene
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EXAMPLE
Name the following structure:

H H
H C C C C H
H CH3
2-methyl-1,3-butadiene or 2-methylbuta-1,3-diene
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EXAMPLE
Name the following structure:

H H CH3 H
H C C C C C C H
H CH3 H H

2,5-dimethyl-1,3-hexadiene or 2,5-dimethylhexa-1,3-diene
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Your Turn!
• Complete practice questions worksheet on naming and drawing
simple hydrocarbons
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SCIENCE UNDERSTANDING
The physical properties of organic compounds are influenced by the
molar masses of the molecules and polarity of functional groups.
qPredict, explain, and compare the melting points, boiling points,
and solubilities in water and non-polar solvents of organic
compounds, given their structural formulae.
BOILING POINTS: EFFECT ON 35

MOLAR MASS (SIZE)

• OBSERVATION: As the molar mass of the molecule increases, the
boiling point also increases.
Alkane Molar Mass (g mol-1) Boiling Point (oC)
Methane 16.042 -162
Ethane 30.068 -89.0
Propane 44.094 -42.0
Butane 58.12 -1.00
Pentane 72.146 36.0
Hexane 86.172 69.0
BOILING POINTS: EFFECT ON 36

MOLAR MASS (SIZE)

• OBSERVATION: As the molar mass of the molecule increases, the
boiling point also increases.
Alcohol Molar Mass (g mol-1) Boiling Point (oC)
Methanol 32.042 64.5
Ethanol 46.068 78.3
Propan-1-ol 60.094 97.2
Butan-1-ol 74.12 117.7
Pentan-1-ol 88.146 138
Hexan-1-ol 102.172 157.1
BOILING POINTS: EFFECT ON 37

MOLAR MASS (SIZE)

• OBSERVATION: Boiling point increases as the molar mass of the
compound with identical functional group increases.

• Why?

ØThink about intermolecular forces

BOILING POINTS: EFFECT ON 38

MOLAR MASS (SIZE)

• OBSERVATION: Boiling point increases as the molar mass of the
compound with identical functional group increases.

• Why?
ØAs the molar mass of the molecule increases, the strength of
dispersion forces increases.
ØThis means, more energy is required to disrupt the molecules.

ØHence, boiling point increases

• Similar effect with melting points (only difference is in the states)

 BOILING POINTS: EFFECT OF 39

POLARITY
𝛿"
H H H H H O
𝛿" 𝛿!
H C C C O H H C C C H
𝛿!
Hydrogen
H H H H H H Dipole-dipole H H
bonding
H O C C C H Interactions 𝛿"
"
H H O
𝛿! 𝛿
H H H
H C C C H
𝛿!
Propan-1-ol H H

b.pt = 97.2 oC Propanal

b.pt = 47.9 oC
 BOILING POINTS: EFFECT OF 40

POLARITY
𝛿 " 𝛿! 𝛿"
H O H Hydrogen
H O H
𝛿!
H C C 𝛿! C H Bonding
𝛿"
C C H
H O 𝛿"
Dipole-dipole H H O H
!
interaction 𝛿"
H C C𝛿
H O H 𝛿!
H O" H
H C C 𝛿! C H 𝛿

H H Ethanoic Acid
Propanone b.pt = 118 oC
b.pt = 56.1 oC
BOILING POINTS: EFFECT OF 41

POLARITY
• OBSERVATION: As the polarity of the molecule increases, the boiling
point also increases.

Compound Formula Molar Mass Boiling Point

(g mol-1) (oC)
Propan-1-ol CH3CH2CH2OH 60.088 97.2

Propanal CH3CH2CHO 58.078 47.9

Propanone CH3COCH3 58.078 56.1

Ethanoic Acid CH3COOH 60.052 118

BOILING POINTS: EFFECT OF 42

POLARITY
Polar hydroxyl group Two Polar hydroxyl
H H H H H group

H C C C O H H O C C O H
H H H H H
Propan-1-ol Ethan-1,2-diol

Compound Formula Molar Mass Boiling Point

(g mol-1) (oC)
Propan-1-ol CH3CH2CH2OH 60.088 97.2

Ethan-1,2-diol OHCH2CH2OH 62.068 197.3

BOILING POINTS: EFFECT OF 43

POLARITY
• OBSERVATION: Boiling point increases as the polarity of compounds
with similar molar masses increases.

• Why?
ØThink about intermolecular forces
BOILING POINTS: EFFECT OF 44

POLARITY
• OBSERVATION: Boiling point increases as the polarity of compounds with similar
molar masses increases.

• Why?

ØThe greater the polarity results in the presence of dipole-dipole interactions

and hydrogen bonding.

ØThis means, the force of attraction between molecules is stronger, requiring

more energy to disrupt the molecules

ØHence, boiling point increases

• Similar effect with melting points (only difference is in the states)

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REVISION: SOLUBILITY
• The ability for a solute to dissolve
Solubility in
Molar Mass
(become solvated) in a solvent Alcohol Water
(g mol-1)
(g/100mL)
ØSolvent must separate and surround
Methanol 32.042 Miscible
solute particles Ethanol 46.068 Miscible

• Dependent on: Propan-1-ol 60.094 Miscible

Butan-1-ol 74.12 7.3

ØSize (molar mass)
Pentan-1-ol 88.146 2.2

ØPolarity Hexan-1-ol 102.172 0.6

Heptan-1-ol 116.198 Immiscible

• Think of “Like Dissolves Like” principle
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SOLUBILITY: EFFECT ON SIZE
• Consider the two structures below:

OH
Butane Propan-1-ol

Molar Mass Solubility in water

Substance Molecular Formula
(g mol-1) (g/100mL)
Butane C4H10 58.12 0.0061
Propan-1-ol C3 H 8 O 60.094 Miscible
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SOLUBILITY: EFFECT ON SIZE
• OBSERVATION: Water solubility decreases as the size of the
compound increases.

• Why?
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SOLUBILITY: EFFECT ON SIZE
• OBSERVATION: Water solubility decreases as the size of the compound
increases.

• Why?
ØAs organic compounds increases in size (molar mass), the overall molecule
becomes more non-polar
ØWater molecules are very polar
ØMakes it more difficult for polar water molecules to separate and surround
solute.

• Think of “Like Dissolves Like” Principle

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SOLUBILITY: EFFECT ON POLARITY
• Consider the two structures below: O
OH
OH
Butan-1-ol Propanoic Acid

Molar Mass Solubility in water

Substance Molecular Formula
(g mol-1) (g/100mL)
Butan-1-ol C4H10O 74.12 7.3
Propanoic Acid C3H6O2 74.078 Miscible
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SOLUBILITY: EFFECT ON POLARITY
• OBSERVATION: Water solubility increases as the compound becomes
more polar.

• Why?
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SOLUBILITY: EFFECT ON POLARITY
• OBSERVATION: Water solubility increases as the compound becomes more
polar.

• Why?

ØPolar functional groups have the ability to form strong intermolecular

forces (dipole-dipole interactions and/or hydrogen bonding) with polar
molecules
ØMore polar = stronger intermolecular forces

ØAllows water to more readily separate and surround solute.

• Think of “Like Dissolves Like” Principle

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Your Turn!
• Complete practice questions worksheet on explaining melting point,
boiling point and solubility between two organic molecules.