ORGANIC CHEMISTRY

Organic chemistry is the study of the structure, properties, compositions, reactions, and preparation of carbon-
containing compounds.

Organic chemistry: Chemistry of carbon compounds.

Carbon has a valency of four on a tetrahedral arrangement. Seeing as it has a valency of four, carbon atoms
can make a total of four BONDS, forming single, double or triple bonds. Carbon forms strong covalent bonds
with itself and many other elements. Carbon is the basic building block of organic compounds that recycles
through the earth’s air, water, soil, and living organisms.

Before we start take note of the following definitions:

Hydrocarbon: Organic compounds that consist of hydrogen and carbon only.

General formula: General formula is a formula for a group of similar organic compounds.

Molecular formula: A chemical formula that indicates the type of atoms and the correct number of each in a
molecule.

Structural formula: A structural formula of a compound shows which atoms are attached to which within the
molecule. Atoms are represented by their chemical symbols and lines are used to
represent ALL the bonds that hold the atoms together.

Condensed structural formula: A formula that shows the way in which atoms are bonded together in the
molecule but does not show all bond lines.

Homologous series: A series of organic compounds that can be represented by the same general formula
and that have the same functional group.
FAMILIES Kardashians,
Weasleys, … OR
A series of organic compounds which one member differs from the next with a CH2
group.

Functional group: A bond or an atom or a group of atoms that determine(s) the physical and chemical
Features, ID, properties of a group of organic compounds.
(ginger = Weasley)

Saturated: Compounds with only single bonds between C atoms in their hydrocarbon chains.
OR
Compounds in which there are no multiple bonds between C atoms in their hydrocarbon
chains.
1
 Parent Number of Carbons
meth - 1
eth - 2
prop - 3
but - 4
pent - 5
hex - 6
hept - 7
oct - 8
non - 9
dec - 10
Substituent (branch): A group or branch attached to the longest continuous chain of C atoms in an
organic compound. (methyl-, ethyl-, etc.)
IUPAC naming: A chemical nomenclature (set of rules) created and developed by the
International Union of Pure and Applied Chemistry (IUPAC) to generate
systematic names for chemical compounds.

Note the following for naming purposes:

- Naming and drawing of organic compounds is restricted to one type of functional group per compound
and to a maximum of two functional groups of the same type per compound, except for haloalkanes,
where a maximum of two different halogen substituents (e.g. bromo- and chloro-) are allowed per
molecule.
- Number the chain starting at the end that it is in such a way that the functional group has the smallest
number.
- The substituent chains (alkyl substituents) that are often used in naming and reactions are: methyl –
Person name
and ethyl- groups.
- Generally, a maximum of three are allowed on the alkane, alkene, haloalkane, alcohol or carboxylic
acid parent chain.
- When naming haloalkanes, the halogen atoms do not get preference over alkyl groups – numbering
should start from the end nearest to the first substituent, either the alkyl group or the halogen. IN
haloalkanes where e.g. a Br and a Cℓ have the same number when numbered from different ends of a
chain, Br gets alphabetic preference.
- When writing IUPAC names, substituents appear as prefixes written alphabetically (bromo-, chloro,
ethyl-, methyl-), ignoring the prefixes di- and tri-.
- When writing IUPAC names, the following conventions must be followed:
o Numbers are separated from letters using a dash (-)
o Numbers are separated from numbers using a comma (,).
o Letters are not separated at all (i.e. no space is used), with the exceptions being esters (e.g.
methyl ethanoate) and carboxylic acids (i.e. propanoic acid).
- For euphonic purposes, the vowel “e” is generally removed from the name before the suffix, e.g. butan-
1-ol instead of butane-1-ol. However, this is not done for diols, e.g. butane-1,2-diol is correct and not
butan-1,2-diol.
- For euphonic purposes, the vowel “a” must be added to the name before the suffix of dienes, e.g. buta-
1,3-diene is correct, and not but-1,3-diene.
In short:
1. Identify the functional group.
2. Look for the longest chain (containing functional group).
3. Identify all substituents.
4. Number the chain (FG smallest, then Sub)

2
5. Name substituents alphabetically then parent then suffix (surname).

3
 Alkanes
- Definition: An organic compound containing only C-H and C-C single bonds.
- Hydrocarbons
- Saturated
- Suffix (Surname): -ane
- General formula: CnH2n+2
- Functional group:

C C

Example:
1. methane
Molecular formula: CH4
Structural formula: H

H C H

H
Condensed formula: CH4

2. ethane
Molecular formula: C2H6
Structural formula: H
H

H C C H

H H
Condensed formula: CH3CH3 or CH3 – CH3

Exercise:
List the first 8 (eight) alkanes. Indicate the IUPAC name, molecular formula, structural formula and condensed
formula.

4
Rules for naming alkanes:
1. Name the parent hydrocarbon.
o Use the longest continuous chain as parent.
o If two chains are of the same length, choose the one with the larger number of substituents.
o Choose the parent name (meth-, eth-, etc.) according to the number of C atoms in the longest
chain.
o Add the suffix –ane.
2. Number the atoms in the parent chain.
o Begin at the end nearest to the first substituent and number each C atom in the parent chain.
o If two substituents are an equal distance away from both ends, begin numbering at the end
nearer to the second substituent.
o If two different substituents can have the same number, the substituent that is alphabetically first
obtains the lower number.
3. Identify and number substituents.
o Name substituents according to the number of C atoms and add the suffix, -yle. CH3– is a
methyl group, CH3CH2– is an ethyl group. In general, these groups are called alkyl groups (a
group formed by removing one H atom from an alkane).
o Assign a number to each substituent according to its point of attachment to the parent chain.
o If two substituents are on the same carbon, they get the same number.
o If more than one type of substituent is present, arrange them alphabetically in front of the parent
name.
o If two or three identical substituents are present, use di-, or tri- as prefix. Do not use these
prefixes for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

Example 1:

H H H H H

H C C C C C H

H H H H H

The IUPAC name of the above compound can be determined as follow:

● The compound is a hydrocarbon with only C – C single bonds = alkane. The name ends on –ane.
● The compound contains 5 C atoms. Consequently, the parent name is pent-.
● There are no substituents, therefore the name of the compound is pentane.

5
Example 2:

The IUPAC name of the above compound can be determined as follows:

● The compound is a hydrocarbon with only C – C single bonds = alkane. The name ends on –ane.
● The longest chain contains 7 C atoms – the parent name is hept-.
● The substituent contains 1 C atom and therefore is a methyl group.
● Numbered from the left, the methyl group is on C5, numbered from the right the methyl group is on C3.
The latter give the lower number. Separate the number and the prefix with a hyphen.
● The compound is 3-methyl heptane.

7 6 5 4 3 2 1

6
Example 3:

The IUPAC name of the above compound can be determined as follows:

● The compound is a hydrocarbon with only C – C single bonds = alkane. The name ends on –ane.
● The longest chain contains 6 C atoms – the parent name is hex-.
● One substituent has 1 C atom – methyl group. Another substituent contains 2 C atoms – an ethyl
group.
● Numbered from the right, the methyl group is on C4 and the ethyl group on C3. Numbered from the left,
the methyl group is on C3 and the ethyl group is on C4. Numbering from either side gives the same
result, but alphabetically ethyl comes before methyl. Commas separate numbers, while hyphens
separate numbers and prefixes.
● The compound is 3-ethyl-4-methylhexane.

6 5 4 3 2 1

7
 Alkenes
- Definition: A compound of carbon and hydrogen that contains a carbon-carbon double bond.
- Hydrocarbons
- Unsaturated
- Suffix (Surname): -ene
- General formula: CnH2n
- Functional group:

C C

Example:

1. ethene
Molecular formula: C2H4
Structural formula: H H

H C C H

Condensed formula: CH2CH2 or CH2=CH2

Rules for naming alkenes:

1. Name the parent hydrocarbon
o Find the longest chain that contains both carbons of the double bond – the number of C atoms
in this chain determines the parent name.
o Use the suffix –ene.
2. Number the atoms in the parent chain.
o Begin at the end nearest to the double bond and number each C atom in the parent chain – the
double bond will receive the lowest possible number.
o If the double bond is the same distance from either side, begin numbering at the end nearest to
the first substituent.
o If two substituents can have the same numbers, the C atom attached to the substituent that is
alphabetically first, obtains the lower number.
o Place the number of the first C atom of the double bond between the parent name and the
suffix. Use a hyphen between the number and the parent name (e.g. but-1-ene).
3. Identify and number substituents.
o Name substituents according to the number of C atoms: methyl (CH3-) or ethyl (CH3CH2-)
o Assign a number to each substituent according to its point of attachment to the parent chain.
(Double bonds have preference in numbering and substituents will not necessarily have the
lowest possible numbers.)
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in the name – ethyl before methyl.
o If two or three identical substituents are present, use di or tri as prefix. Do not use these prefixes
for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

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Example 1:

H H H H H

H C C C C C H

H H H
The IUPAC name of the above compound can be determined as follows:
- The compound is a hydrocarbon with a carbon-carbon double bond = alkene. The name ends on –ene.
- The longest chain containing the double bond has 5 C atoms – the parent name is pent-.
- If numbered from the right, the double bond is after C2. If numbered from the left, the double bond is
after C3. The former gives the double bond the lower number.
- Place the number of the double bond between the parent name and the suffix. Use a hyphen between
the numbers and the suffix, and between the number and the parent name.
- The compound name is pent-2-ene.

Example 2:
H H

H H H C H H C H H

H C C C C C C H

H H H C H H H

H C H

H
The IUPAC name of the above compound can be determined as follows:
- The compound is a hydrocarbon with a carbon-carbon double bond = alkene. The name ends on –ene.
- The longest chain containing the double bond has 6 C atoms – the parent is hex-.
- If numbered from the right, the double bond is after C2. If numbered from the left, the double bond is
after C4. The former gives the double bond the lower number.
- Place the number -2- of the double bond between the parent name and the suffix. Use a hyphen
between the number and the suffix and between the number and the parent name.
- The substituents are on C3 and C4. Ethyl before methyl and two methyl groups become dimethyl.
- The compound name is 4-ethyl-3,4-dimethylhex-2-ene.

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 Alkynes
- Definition: A compound of carbon and hydrogens that contains a carbon-carbon triple bond.
- Hydrocarbons
- Unsaturated
- Suffix (Surname): -yne
- General formula: CnH2n-2
- Functional group:
C C

Rules for naming alkynes:

1. Name the parent hydrocarbon
o Choose the parent name to the number of C atoms in the longest chain containing both carbons
of the triple bond.
o Use the suffix –yne.
2. Number the atoms in the parent chain.
o Begin at the end nearest to the triple bond and number each carbon in the parent chain - the
triple bond carbons receive the lowest possible numbers.
o If the triple bond is the same distance from either side, begin numbering at the end nearest the
first substituent.
o If two substituents can have the same number, the C atom attached to the substituent that is
alphabetically first, obtains the lower number.
o Place the number of the triple bond between the parent name and the suffix.
o Use a hyphen between the number and the suffix, and between the number and the parent
name e.g. pent-2-yne.
3. Identify and number the substituents.
o Name substituents according to the number of C atoms: methyl (CH3–) or ethyl (CH2CH3–).
o Assign a number to each substituent according to its point of attachment to the parent chain.
(Triple bonds have preference in numbering and alkyl groups will not necessarily have the
lowest possible numbers.)
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically – ethyl before methyl.
o If two or three identical substituents are present, use di or tri as prefix. Do not use these prefixes
for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

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Example 1:
H

H C H

H H C H H H

H C C C C C C H

H H H C H H

H
The IUPAC name of the above compound can be determined as follows:
- The compound is a hydrocarbon with a carbon-carbon triple bond = alkyne. The name ends on –yne.
- The longest chain containing the triple bond has 7 C atoms – the parent name is hept-.
- Numbered from the left, the triple bond is after C5. Numbered from the other end of the chain, the triple
bond is after C2. The latter gives a lower number.
- Place the number -2- of the triple bond between the parent name and the suffix. Use a hyphen between
the number and the suffix and between the number and the parent name.
- The substituents, two methyl groups, are on C4 and C5.
- The compound is 4,5-dimethylhept-2-yne.

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 Haloalkanes
- Definition: An organic compound in which one or more H atom(s) in an alkane have been replaced with
halogen atoms.
- Saturated
- General formula: CnH2n+1X (X = F, Cℓ, Br, I)
- Functional group:

C X

Rules for naming haloalkanes:

1. Name the parent. (similar to the rules for alkanes)
o Find the longest chain.
o If two chains are of the same length, choose the one with the larger number of substituents.
o Choose the parent name according to the number of C atoms in the longest chain.
o Add the suffix –ane.
2. Number the atoms in the parent chain
o Number the C atoms of the parent chain beginning at the end nearer the first substituent,
regardless whether it is alkyl or halo.
o If two substituents (alkyl or halo) are an equal distance away from both ends, begin numbering
at the end nearer to the second substituent – substituents must have the lowest number
possible.
o If two different substituents can have the same number, the substituent that is alphabetically first
obtains the lower number.
3. Identify and number substituents.
o Name alkyl substituents according to the number of C atoms: methyl or ethyl.
o Name halogen substituents as chloro, bromo, iodo or fluoro.
o Assign a number to each substituent according to its position on the chain.
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in front of the parent name.
o If two or three identical substituents are present, use di or tri as prefix. Do not use these prefixes
for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

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Example 1:
H H Br H H

H C C C C C H

H Br H
H
H C H

H
The IUPAC name of the above compound can be determined as follows:
- The compound is an alkane containing two halogen atoms = haloalkane. The longest chain contains 5
C atoms – the parent name is pentane.
- Three substituents are present: a methyl group and two bromine atoms. Numbered from the left, the
methyl group is on C4, and the Br atoms on C3. Numbered from the right, the methyl group is on C2,
and the Br atoms on C3. The latter gives the lower numbers.
- Alphabetically bromo comes before methyl.
- The compound is 3,3-dibromo-2-methylpentane.

Example 2:
H H H H H H

H C C C C C C H

H Cℓ H H
H
H C H

H
The IUPAC name of the above compound can be determined as follows:
- The compound is an alkane containing a halogen atom = haloalkane. The longest chain contains 6 C
atoms – the parent name is hexane.
- Two substituents are present: a methyl group and one chlorine atom. Numbered from either side gives
the same result, substituents on C3 and C4, but alphabetically chloro comes before methyl.
- The compound is 3-chloro-4-methylhexane.

13
Haloalkanes can be classified as primary, secondary or tertiary depending on the number of C atoms bonded
to the carbon with the halogen.

Primary haloalkane Secondary haloalkane Tertiary haloalkane

The C atom bonded to the The C atom bonded to the The C atom bonded to the
halogen is bonded to ONE other C halogen is bonded to TWO other halogen is bonded to THREE
atom. C atoms. other C atoms.

14
 Alcohols
- Definition: An organic compound in which H atoms in an alkane have been substituted with hydroxyl
groups (-OH groups).
- Saturated
- Suffix: -ol
- General formula: CnH2n+1OH
- Functional group:

C O H

- The hydroxyl group

Rules for naming alcohols:

1. Name the parent.
o Find the longest chain containing the hydroxyl group.
o Choose the parent name according to the number of C atoms in the longest chain.
o Replace the –e of the corresponding alkane with the –ol.
2. Number the atoms in the parent chain.
o Number the C atoms of the parent chain beginning at the end nearer to the hydroxyl group.
o The position of the hydroxyl group is indicated as a number between the parent and suffix –ol.
o If the hydroxyl group is the same distance from either side, begin numbering at the end nearest
to the first substituent.
o If two substituents can have the same number, the C atom attached to the substituent that is
alphabetically first, obtains the lower number.
3. Identify and number the substituents.
o Name alkyl substituents according to the number of C atoms.
o Assign a number to each substituent according to its position on the chain.
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in the name.
o If two or three identical substituents are present, use di or tri as prefix. Do not use these prefixes
for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

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Example 1:
H H H H

H C C C C H

H H O H

H
- The compound is an alkane containing a hydroxyl group = alcohol. The suffix –ol replaces the –e in the
corresponding alkane.
- The longest chain containing the hydroxyl group has 4 C atoms. The parent name is but.
- Numbered from the right, the hydroxyl group is on C2. Numbered from the left the hydroxyl group is on
C3. The former gives the lower number. The number is written between the parent and the suffix. Use
hyphens to separate the number from the parent name and from the suffix.
- The compound is butan-2-ol.

Example 2:
H

H C H
H

H C H H C H
H H H H H

H C C C C C C C H

H H H O H H
H

H
- The compound is an alkane containing a hydroxyl group = alcohol. The suffix –ol replaces the –e in the
corresponding alkane.
- The longest chain containing the hydroxyl group has 8 C atoms. The parent name is oct.
- Numbered from the right, the hydroxyl group is on C5. Numbered from the left it is on C4. The latter
gives the lower number. The number is written between the parent and the suffix. Hyphens separate
the number from the parent name and from the suffix.
- Two substituents are present: two methyl groups on C3 and C6.
- The compound is 3,6-dimethyloctan-4-ol.

16
Like haloalkanes, alcohols can be classified as primary, secondary or tertiary depending on the number of C
atoms bonded to the carbon containing the hydroxyl group. .

Primary alcohol Secondary alcohol Tertiary alcohol

The C atom bonded to the The C atom bonded to the The C atom bonded to the
hydroxyl group is bonded to ONE hydroxyl group is bonded to TWO hydroxyl group is bonded to
other C atom. other C atoms. THREE other C atoms.

17
 Aldehydes
- Definition: Organic compounds having the general structure RCHO where R = H or alkyl.
- Saturated
- Suffix: -al
- General formula: CnH2nO
- Functional group:
O

C H
- The formyl group

Rules for naming aldehydes:

1. Name the parent.
o Find the longest chain containing the –CHO group.
o Choose the parent name according to the number of C atoms in the longest chain.
o Replace the –e of the corresponding alkane with the suffix –al.
2. Number the atoms in the parent chain.
o If no substituents are present, NO numbering takes place.
o If substituents are present, the C atoms of the parent chain are numbered beginning at the C
atom of –CHO group. Omit this number (of C1) in the name.
3. Identify and number the substituents.
o Name alkyl substituents according to the number of C atoms: methyl (CH3-) or ethyl (CH3CH2-)
o Assign a number to each substituents according to its position on the chain.
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in the name.
o If two or three identical substituents are present, use di or tri as prefix. DO not use these
prefixes for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

Example 1:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a formyl group (-CHO) = aldehyde. The suffix –al replaces the –e in the name
of the corresponding alkane.
- The longest chain containing the formyl group has 4 C atoms. The parent name is but-.
- No substituents are present – no numbering takes place.
- The compound is butanal.

18
Example 2:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a formyl group (-CHO) = aldehyde. The suffix –al replaces the –e in the name
of the corresponding alkane.
- The longest chain containing the –CHO group has 6 C atoms. The parent name is hex-.
- One substituents is present: a methyl group on C4 (the formyl group is C1).
- The compound is 4-methylhexanal.

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 Ketones
- Saturated
- Suffix: -one
- General formula: CnH2nO
- Functional group:
O

C C C

- The carbonyl group

Rules for naming ketones:

1. Name the parent.
o Find the longest chain containing the carbonyl group.
o Choose the parent name according to the number of C atoms in the longest chain.
o Replace the –e of the corresponding alkane with the suffix –one.
2. Number the atoms in the parent chain.
o Number the chain from the end nearest to the carbonyl group – the carbonyl carbon always
receives the lower number.
o The position of the carbonyl group is indicated as a number between the parent name and the
suffix –one.
o If the carbonyl group is the same distance from either side, begin numbering at the end nearest
the first substituent.
o If two substituents can have the same number, the C atom attached to the substituent that is
alphabetically first, obtains the lower number.
3. Identify and number the substituents.
o Name alkyl substituents according to the number of C atoms: methyl (CH3-) or ethyl (CH3CH2-)
o Assign a number to each substituents according to its position on the chain.
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in the name.
o If two or three identical substituents are present, use di or tri as prefix. DO not use these
prefixes for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

20
Example 1:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a carbonyl group = ketone. The –e in the corresponding alkane is replaced by
–one.
- The longest chain containing the carbonyl group has 7 C atoms. The parent name is hept.
- Numbered from the left, the carbonyl C atom is C4. Numbered from the right it is also C4. No
substituents are present therefore it does not matter.
- The number is written between the parent name and the suffix. Hyphens separate numbers from the
parent and the suffix.
- The compound is heptan-4-one.

Example 2:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a carbonyl group = ketone. The –e in the corresponding alkane is replaced by
–one.
- The longest chain containing the carbonyl group has 7 C atoms. The parent name is hept.
- Numbered from the left the carbonyl group is on C6. Numbered from the right it is on C2. The latter
gives the lower number. The number is written between the parent name and the suffix. Hyphens
separate numbers from the parent name and from the suffix, i.e. heptan-2-one.
- The compound is 3,5-dimethylheptan-2-one.

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 Carboxylic Acids
- Definition: An organic compound containing a carboxyl group.
- Suffix: -oic acid
- General formula: CnH2nO2
- Functional group:
O

C O H
- The carboxyl group

Rules for naming of carboxylic acids:

1. Name the parent.
o Find the longest chain containing the carboxyl group.
o Choose the parent name according to the number of C atoms in the longest chain.
o Replace the –e of the corresponding alkane with the suffix –oic acid.
2. Number the atoms in the parent chain.
o If no substituents are present, NO numbering takes place.
o If substituents are present, the C atoms of the parent chain are numbered beginning at the C
atom of the carboxyl group which is always C1. Omit this number (of C1) in the name.
3. Identify and number the substituents.
o Name alkyl substituents according to the number of C atoms: methyl (CH3-) or ethyl (CH3CH2-)
o Assign a number to each substituents according to its position on the chain.
o If two substituents are on the same carbon, they get the same number.
o Arrange substituents alphabetically in the name.
o If two or three identical substituents are present, use di or tri as prefix. DO not use these
prefixes for alphabetical purposes.
o Use hyphens to separate numbers and prefixes, commas to separate numbers.

Example 1:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a –COOH group = carboxylic acid. The suffix –oic acid replaces the –e in the
corresponding alkane.
- The longest chain containing the carboxyl group has 4 C atoms. The parent name is but-.
- No substituents are present therefore no numbering is needed.
- The compound is butanoic acid.

22
Example 2:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a –COOH group = carboxylic acid. The suffix –oic acid replaces the –e in the
corresponding alkane.
- The longest chain containing the carboxyl group has 6 C atoms. The parent name is hex-.
- Two substituents are present. The carboxyl C atom is always C1, but the number is not shown in the
name. An ethyl group is on C2 and a methyl group is on C4. Hyphens separate numbers and prefixes.
- The compound is 2-ethyl-4-methylhexanoic acid.

23
 Esters
- General formula: CnH2nO2
- Functional group:
O

C O C

Esters are derivatives of carboxylic acids and can be prepared by the reaction of an alcohol and a carboxylic
acid. The name of esters has two part: the first part comes from the alcohol and the last part from the
carboxylic acid from which it is derived.

Rules for naming esters:

An ester has two groups that must be named:
- An acyl group (RCO-), originally from a carboxylic acid
- An alkyl group (R’) bonded to an O atom, originally from an alcohol.

1. Naming the alkyl group:

o Count the number of C atoms in the alkyl group.
o Choose the parent name according to the number of C atoms in the alkyl chain.
o Name is as an alkyl group by changing the –ane in the parent alkane to –yl (e.g. methyl, ethyl,
etc.).
o This becomes the first part of the name of the ester.
2. Naming the acyl group.
o Count the number of C atoms in the acyl group.
o Choose the parent name according to the number of C atoms in the group.
o First name the group as its parent carboxylic acid (acid from which it was obtained).
o Finally name the second part of the name of the ester by changing the –ic acid in the parent
carboxylic acid to –ate.

Example 1:

The IUPAC name of the above compound can be determined as follows:

- The compound contains a –COOR group = ester.
- The ester has two groups, an alkyl and an acyl group, that are named separately:

24
- The alkyl group (originally from butanol) has 4 C atoms. The parent alkane, butane, is changed to an
alkyl group, i.e. butyl. This is the first part of the name of the ester.
- The acyl group (originally from propanoic acid) has 3 C atoms. The parent acid is propanoic acid. The
–ic acid is changed to –ate, i.e. propanoate. This is the second part of the name of the ester,
- The name of the compound is butyl propanoate.

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 Isomers
Most organic molecules have a molecular formula that corresponds with that of another molecule. This
property is called isomerism. Isomers are compounds with the same molecular formula, but different
structures. Organic compounds show different types of isomers.

Structural isomers: Organic molecules with the same molecular formula, but different structural formulae.

Two compounds that are structural isomers only differ in the way in which atoms are arranged in the
molecules. For example;
C4H10 can be either one of the following compounds:

These two compounds have the same number and type of atoms. But are different compounds due to the
different arrangement of the atoms.

Structural isomers can be further divided into chain isomers, positional isomers and functional isomers.

Chain isomers: Compounds with the same molecular formula, but different types of chains.

Positional isomers: Compounds with the same molecular formula, but different position of the side chain,
substituents or functional groups on the parent chains.

Functional isomers: Compounds with the same molecular formula, but different functional groups.

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Esters + Carboxylic
Acids

27
 Physical Properties
Physical properties, e.g. boiling point, can give important clues to other physical properties and structural
characteristics of compounds.

Types of physical properties

Physical properties include the following:
- Phase
- Boiling point
- Melting point
- Volatility (How easily a liquid change into a gas)
- Vapour pressure
- Viscosity (measure of a liquids resistance to flow)
- Solubility (how easily a substance dissolves in non-polar solvents)

The types of physical properties that will be studied in more depth are defined in the table below:
Physical Property Definition
Boiling Point The temperature at which the vapour pressure of a substance equals atmospheric
pressure

At this temperature the liquid is converted into a gas. Energy is needed to overcome
the IMF in the more ordered liquid phase.
Melting point The temperature at which the solid and liquid phase of a substance are at equilibrium.

Energy is needed to overcome the IMFs.

Vapour pressure The pressure exerted by a vapour at equilibrium with its liquid in a closed system.

Substances with high vapour pressure are volatile, and have a low boiling point.

Physical properties of organic compounds are mainly determined by the strength of intermolecular forces.

Types of intermolecular forces

Intermolecular forces are the interactions that exist between molecules. The THREE different types of IMF that
can exist between organic molecules are, in order of increasing strength:
● London forces (dispersion forces)
● Dipole-dipole forces
● Hydrogen bonding

Type of intermolecular
Cause
force (Van der Waals force)
Caused by the interaction of temporary dipoles, non-polar molecules. All
London forces compounds exhibit London forces. The larger the surface area, the
stronger the London force.
Caused by the interaction between permanent dipoles of two polar
Dipole-dipole forces
molecules.
Caused by the electrostatic interaction of a H atom in a O-H, N-H or H-F
Hydrogen bonding
bond with the lone pair of an N, O or F atom in another molecule.

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The table below links the homologous series discussed to the type of IMF that can be found between molecues
in each:

Alkane Aldehydes
Alcohols
Homologous series Alkene Ketones
Carboxylic acids
Alkyne Haloalkanes
London forces
London forces
Type of IMF London forces Dipole-dipole forces
Dipole-dipole forces
Hydrogen bonding

Hydrogen bonding exists between molecules of alcohols and carboxylic acids. In carboxylic acids hydrogen
bonds are formed and accepted on TWO O atoms. Alcohols have one site for hydrogen bonding while
carboxylic acids have two. Therefore, the IMF in alcohols will be weaker than those in carboxylic acids.

Factors determining physical properties:

1. Type and strength of intermolecular force
2. Molecular size / chain length
3. Amount of branching
4. Number of similar functional groups

1. The type and strength of the intermolecular force:

● This is determined by the type of functional group present.
● Molecules have different degrees of polarity as determined by the functional group present.

Polarity ranking of functional groups:

Carboxylic acid > Alcohol > Ketone ~ Aldehydes > Esters > Hydrocarbons
● The grater the polarity of the molecules, the greater the IMF and the higher the boiling point.
● This is the case because more energy is required to overcome the IMF.
● The higher the polarity, the stronger the IMF, the more energy is needed to overcome the IMF and
therefore the higher the boiling point, the higher the viscosity and the lower the vapour pressure.

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2. Molecular size / chain length:
● For compounds of the same functional group the chain length plays a role in the strength of the IMF.
● The longer the carbon chain, the larger the surface area and the stronger the London forces between
the molecules.
● A larger surface area has more sites where London forces can form. The combined effect of all the
London forces results in stronger intermolecular forces, and thus a higher boiling point, lower vapour
pressure and higher melting point.
● This is due to the fact that more energy is required to overcome the intermolecular forces.

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3. Amount of branching:
● For compounds of the same functional group and comparable molecular mass, branching plays a role
in the strength of IMF.
● The more branched a compound is, the more spherical its structure and so the contact surface area is
smaller.
● Therefore, the smaller the contact surface area the weaker the IMF between the molecules.
● This then leads to a lower boiling point, higher vapour pressure and lower melting point.
● Not as much energy is needed to overcome the IMF.

4. Number of functional groups:

● The more halogens, hydroxyl-, carbonyl-, formyl- or carboxyl groups are present the higher the melting
and boiling point and the lower the vapour pressure.
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32
 ORGANIC MOLECULES
Hydrocarbons
Homologous Carboxylic
Haloalkanes Esters Aldehydes Ketones Alcohols
series Alkanes Alkenes Alkynes Acids

General
CnH2n+2 CnH2n CnH2n-2 CnH2n+1X CnH2nO2 CnH2nO CnH2nO CnH2n+1O CnH2nO2
Formula

Functional
Group

Example of
structural
formula

Example of bromoethan methyl

ethane ethene ethyne ethanal propanone ethanol ethanoic acid
IUPAC name e ethanoate

London Forces
Intermolecula
Dipole-dipole Forces
r Forces
Hydrogen Bonding

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34
 Reactions
Two applications of organic chemistry are combustion reactions to release energy and the preparation of
esters which are used as flavouring.

COMBUSTION:
Combustion is also referred to as oxidation reactions. Alkanes are our most important fossil fuels and the main
source of various kinds of energy such as heat energy, energy for powering cars, the generation of electricity,
etc.

Alkanes will burn in oxygen (air) to form water and carbon dioxide – when oxygen is in excess. This is referred
to as complete combustion. When oxygen is the limiting reactant then carbon monoxide (CO) and water will
form instead of CO2.

Large quantities of energy are released during combustion. The combustion of hexane, an ingredient of petrol,
can be represented as follows:

2C6H14 + 19O2  12CO2 + 14H2O + energy

ESTERIFICATION:
An ester can be prepared from the reaction between an alcohol and carboxylic acid in the presence of a strong
acid. Esters tend to have pungent smells and are also used in the flavouring of, for example, sweets.

Alcohol + Carboxylic acid  Ester + Water

Certain conditions need to be met. Concentrated sulphuric acid (H2SO4) needs to be present as catalyst and
heat added.

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ORGANIC REACTIONS

36
37