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MODULE 4
CORE ORGANIC
CHEMISTRY
CHEMISTRY
NOTES
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INDEX
TOPIC 1: BASIC CONCEPTS AND HYDROCARBONS. . . . . . . . . . 4
Section 1: Basic Concepts of Organic Chemistry. . . . . . . . . . . . . . . . . . . . . . . . . . 5
Section 2: Alkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
Section 3: Alkenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
TOPIC 2: ALCOHOLS, HALOALKANES AND ANALYSIS . . . . . . . . 21
Section 1: Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
Section 2: Haloalkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
Section 3: Organic Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
Section 4: Analytical techniques. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
3
TOPIC 1
Basic Concepts
and
Hydrocarbons
SECTION 1:
Basic Concepts
of Organic Chemistry
1 IUPAC nomenclature
for systematic naming of compounds
•• Specific naming system used to give unambiguous names to compounds
•• Three parts to a name: stem, suffix and prefix
•• Stem: main part, depends on the longest carbon chain in a molecule
•• Based on name of the alkane that corresponds to the longest carbon chain
Alkane
Number of C atoms in the main carbon chain
Methane
1
Ethane
2
Propane
3
Butane
4
Pentane
5
Hexane
6
Heptane
7
Octane
8
Nonane
9
Decane
10
•• Suffix: end of the name, identifies the most important functional group
•• If a suffix starts with a vowel the -e at the end of the alkane stem is dropped
•• Prefix: start of the name, identifies any other functional groups and the carbons they’re attached to
Functional group
Formula
Alkanes
C-C
-ane
Alkenes
C=C
-ene
Haloalkanes
-F
fluoro-
-Cl
chloro-
-Br
bromo-
-I
iodo-
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Prefix
Suffix
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Functional group
Formula
Prefix
Suffix
Alcohols
-OH
hydroxy-
-ol
Carboxylic Acid
-COOH
-oic acid
Aldehydes
-CHO
-al
Ketones
C-CO-C
-one
•• Numbers are used to indicate the location of a carbon side chain or functional group on the
main chain
•• Dashes separate numbers from words
•• Commas separate numbers
•• To name a compound
○○ Identify the longest carbon chain and the right alkane stem
○○ Identify the most important functional group and which carbon on the carbon chain it is
attached to
○○ Attach the suffix to the stem with number of the carbon it’s on before it, removing the -e
from the stem if needed
○○ Identify any other functional groups and add them as prefixes
○○ Prefixes are written in alphabetical order, numbering the carbons so that the smallest
numbers possible are used
○○ di- indicates two identical functional groups, tri- three and tetra- four
•• Aldehydes and carboxylic acids don’t need numbers because they’re always at the end of a
chain
•• Alkanes with a hydrogen removed are called alkyl groups
•• They’re added as prefixes when attached to the main carbon chain
Alkyl group
Number of C atoms in the side carbon chain
Methyl
1
Ethyl
2
Propyl
3
Butyl
4
Pentyl
5
Hexyl
6
Heptyl
7
Octyl
8
Nonyl
9
Decyl
10
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2 Interpreting structures
•• General formula: the simplest algebraic formula of a member of a homologous series,
represents the actual number of atoms in each molecule e.g. C4H10
•• Structural formula: shows number of atoms present and way in which they are arranged
relative to each other
•• Displayed formula: shows actual places of the atoms and nature of the bonds between them
•• Skeletal formula: carbon and hydrogen atoms omitted with carbon atoms represented by
junctions between bonds
3 Functional groups and homologous series
•• Functional group: a group of atoms responsible for the characteristic reactions of a compound
•• Homologous series: a series of organic compounds having the same functional group but
with each successive member differing by CH2
•• Homologous series generally have similar chemical properties
•• Their physical properties change as each unit of CH2 is added
•• Their molecular formula can be worked out from a basic formula for the series
•• Alkyl group: an alkane missing a single hydrogen, can be a side chain on other carbon chains
•• Formula CnH2n+1 e.g. propyl CH3CH2CH2 (C3H7)
•• Aliphatic: a compound containing carbon and hydrogen joined together in straight chains,
branched chains or non-aromatic rings e.g. 2,3-dimethylpentane
•• Alicyclic: an aliphatic compound arranged in non-aromatic rings with or without side chains
e.g. cyclohexane
•• Aromatic: a compound containing a benzene ring
•• Saturated: a compound with single carbon–carbon bonds only
•• Unsaturated: the presence of multiple carbon–carbon bonds, including C = C, triple bonds
and aromatic rings
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