Organic Chemistry

1
Organic Chemistry

• Organic chemistry is the study of carbon
  containing compounds derived from living
  organisms.

2
Organic Compounds

• Contain C bonded to other elements, commonly H,
  O, N, S, and halogens
• Carbon
• Can form many different compounds due to its
  hybrid orbitals
• Has intermediate electonegativity, so its most
  likely to form molecular compounds (Recall
  molecular compounds have diverse properties)
• Can make single, double, and triple bonds
• Can form isomers (same molecular formula but
  different arrangement of atoms)

3
Isomers

• Structural Isomers have the same molecular
  formula but the atoms are bonded together in a
  different sequence
• Stereoisomers are molecules with the same
  molecular formula, a same sequence of atoms but
  they have different 3D orientations

4
Stereoisomers

• Diastereomers form around a double bond and each
  carbon atom involved in the bond must have
  different types of atoms bonded to it
• Enantiomers are mirror images of each other

5
Types of Hydrocarbons

• Saturated Contain the maximum number of
  hydrogens, single bonds between all carbons
• Unsaturated Contain 1 double or triple bonds

6
Types of Hydrocarbons

• Aliphatic Carbons are arranged in chains
• Cyclic Carbons are arranged in rings
• Aromatic Contain a benzene ring

7
Types of Hydrocarbons
8

• Homologous series
• This is a series of compounds which all contain
  the same functional group, and have similar
  chemical properties. 
• ALKANES ALKENES ALCOHOLS
• CH4 CH2 CH2 CH3OH
• CH3-CH3 CH2 CH CH3 CH3CH2OH
• Each has a general formula
• ALKANES CnH2n2
• The members of the series differ by the number of
  CH2 units.
• CH3-CH3, CH3-CH2-CH3, CH3-CH2-CH2-CH3
• Graduation in physical properties  eg boiling
  points.
• CH4 (GAS), C8H18 (LIQUID), C30H62 (SOLID)

9
Rules for Naming Alkanes (Nomenclature)

• For a branched hydrocarbon, the longest
  continuous chain
• of carbon atoms gives the root name for the
  hydrocarbon

1
2
3
4
4 carbon chain butane
10
Naming Alkanes

• Based off the number of C atoms in the longest
  chain
• Count the number of Cs in the longest chain
• Determine the appropriate root
• Add the suffix ane

11
Hydrocarbon Root Names
of Carbons Root Name
1 meth-
2 eth-
3 prop-
4 but-
5 pent-
6 hex-
7 hept-
8 oct-
9 non-
10 dec-
12
Examples

• Butane
• Heptane

13
Naming Branched Alkanes

• Based off the number of C atoms in the longest
  chain
• Count the number of Cs in the longest chain
• Determine the appropriate root
• Use the numbered Cs to give the branches a
  position number add yl suffix
• Add the suffix ane

14
Naming Branched Alkanes

• Important Rules
• Start numbering from the end that will give you
  the lowest number of branches
• If there is more than one type of branch, name
  the branches in alphabetical order
• If there is more than two of the same type of
  branch, give the branch a position number and
  prefixes di, tri tetra etc.
• Put commas between numbers and hyphens between
  numbers and letters

15
Rules for Naming Alkanes (Nomenclature)

• When alkane groups appear as substituents, they
• are named by dropping the -ane and adding -yl.

CH3 Methyl
CH2CH3 Ethyl
CH2CH2CH3 Propyl
CH2CH2CH2CH3 Butyl
Methyl
16
Rules for Naming Alkanes (Nomenclature)

• The positions of substituent groups are specified
• by numbering the longest chain of carbon atoms
• sequentially, starting at the end closest to the
• branching.

1
2
3
4
Methyl
17
Rules for Naming Alkanes (Nomenclature)

• The location and name of each substituent are
• followed by the root alkane name. The
  substituents
• are listed in alphabetical order (irrespective of
  any
• prefix), and the prefixes di-, tri-, etc. are
  used to
• indicate multiple identical substituents.

1
2
3
4
Name
2-methylbutane
Methyl
18
Nomenclature Practice
Name this compound
1
9 carbons nonane
2
4
3
5
6
7
8
9

• Step 1 For a branched hydrocarbon, the longest
  continuous chain of carbon atoms gives the root
  name for the hydrocarbon

19
Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
7
chlorine chloro
8
9
Step 2 When alkane groups appear as
substituents, they are named by dropping the -ane
and adding -yl.
20
Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
7
chlorine chloro
8
9
1
9
NOT
9
1

• Step 3 The positions of substituent groups are
  specified by numbering the longest chain of
  carbon atoms sequentially, starting at the end
  closest to the branching.

21
Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
7
chlorine chloro
8
9
2-chloro-3,6-dimethylnonane

• Step 4 The location and name of each
  substituent are followed by the root alkane name.
  The substituents are listed in alphabetical order
  (irrespective of any prefix), and the prefixes
  di-, tri-, etc. are used to indicate multiple
  identical substituents.

22
Cyclic Alkanes
Cyclopropane, C3H6
Cyclobutane, C4H8
Cyclopentane, C5H10
Cyclohexane, C6H12
Cycloheptane, C7H14
Remember, explicit hydrogens are left out
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Practice

• P. 11-16 1, 2

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Structural Shorthand
Explicit hydrogens (those required to complete
carbons valence) are usually left off of
drawings of hydrocarbons
C1
C2
C3
C4
C1
C3
C4
C2
Line intersections represent carbon atoms
25
Different Methods of Displaying Compounds

• Molecular Formula
• Condensed Structural Formula

• Expanded Molecular Formula
• Structural Formula
• Line Formula

26
Naming Alkenes Alkynes

• Count the number of Cs in the longest chain
  containing the double/triple bond.
• This is the parent chain, determine the root
• Number the parent chain so that the double/triple
  bond has the lowest possible position number
• Identify the position numbers of branches
• Same rules as before
• Write the branches in alphabetical order
• Write the root, including a prefix that
  identifies the position of the double/triple bond
• Add the prefix cyclo if its cyclic
• Add the suffix ene or yne

27
Naming Alkenes Alkynes
28
Naming Aromatics

1. Same rules
2. If benzene is the parent chain benzene suffix
3. If benzene is a branch group phenyl

29
Practice

• P. 16-22 3-7, 8abc
• Naming Alkenes/Alkynes Worksheet
• Isomer Challenge Worksheet
• Naming Hydrocarbons Worksheet