Functional groups'

1
Chapter 3

• Functional groups.
• Alkanes and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.

2
Functional groups
alkane
alkene
alkyne
arene
halide
3
Functional group
carbonyl
water
aldehyde
H
alcohol
ketone
ether
acid
thiol
ester
sulfide
amide
amine
4
Functional group
and others, see page 76 Table 3.1
5
Chapter 3

• Functional groups.
• Alkane and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.

6
Alkanes

• Hydrocarbons, Aliphatic, Paraffins
• Saturated - CnH2n2
• Straight, open, normal, and branched chain
• Constitutional Isomers
• Naming methane to decane

7
Alkanes - Straight, open, normal, and branched
chain
C3H8
C4H10
branched
C5H12
C6H14
C7H16
Straight, open, normal
8
Alkanes - Constitutional Isomers
Graph theory - 1874
See Table 3.2 on p82
C6H14
6
5
4
3
9
Alkanes - Names of straight chain
Table 3.3 on p83 - Methane - Decane
10
Alkyl groups

• Partial structure of alkane - H atom removed.
• Unstable.
• Name - replacing -ane by -yl.
• 1o, 2o, 3o, 4o.

11
Alkyl groups

• -CH3 methyl
• -CH2CH3 ethyl
• -CH2CH2CH3 propyl
• -CH2CH2CH2CH3 butyl
• -CH(CH3)2 iso-propyl
• -C(CH3)3 tert-butyl
• see Tables 3.4 (p 84) Figure 3.3 (p 85).

12
Alkyl groups - 1o, 2o, 3o, 4o
2o
3o
1o
4o
13
Chapter 3

• Functional groups.
• Alkanes and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.

14
IUPAC Name of alkanes

• Find the parent hydrocarbon (i.e. the longest
  chain).
• Number the atoms in the main chain.
• Identify and number the substituents.
• Write the name in a single word.
• Name a complex substituent just as though it were
  itself a compound.

15
IUPAC Name of alkanes
-hexane
2,2,3,3-Tetramethyl
16
Chapter 3

• Functional groups.
• Alkanes and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.

17
Alkane Properties

• Non-polar.
• Low energy barrier rotation.
• Chemically inert.
• CnH2n2 (3n1)/2O2(g) ? nCO2(g) (n1)H2O(g)
• CH4 Cl2

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Alkane Properties - non-polar
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Alkane Properties - Low energy barrier rotation
21
Alkane Properties - reactions
Chemically inert, except ...
22
Chapter 3

• Functional groups.
• Alkanes and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.

23
Cycloalkane

• Alicyclic alkane.
• CnH2n
• Less flexible than straight chain (C3-C7).
• Non-polar.
• Naming.
• Stereoisomers.

24
Alicyclic alkane
cyclopropane
cyclobutane
cyclopentane
cyclohexane
cyclohexane
cyclohexane
cycloheptane
cyclooctane
25
Less flexible
n 11
n 3
cyclopropane
cycloundecane
26
IUPAC Name of cycloalkane

• Find the parent.
• Number the substituents

1,4-Dimethylcyclohexane
3-Cyclobutylpentane
1- Methy-3-propylcyclopentane
1-Bromo-4-ethylcyclodecane
1-tert-butyl-2-methylcyclohexane
4-Bromo-1-tert-butyl-2-methylcycloheptane
27
Bicycloalkane
Bridge
6
4
Bridgehead carbon
3
5
1
2
28
Stereoisomers of cycloalkane
Constitutional isomers
Stereoisomers
29
Stereoisomers of cycloalkane
30
Stereoisomers of cycloalkane

• Identify the carbon as 1o, 2o, 3o, 4o.
• Give the IUPAC name

31
Stereoisomers of cycloalkane
Which stereoisomer is energetically more stable?
32
Chapter 3

• Functional groups.
• Alkanes and alkyl groups.
• IUPAC name of alkanes
• Properties of alkane.
• IUPAC name of cycloalkanes.
• Properties of cycloalkanes.