carey chapter 2 – hydrocarbon frameworks “alkanes” hydrocarbonshydrocarbons...
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Carey Chapter 2 – Hydrocarbon Frameworks
“Alkanes”
HydrocarbonsHydrocarbonsHydrocarbonsHydrocarbons
AromaticAromaticAromaticAromaticAliphaticAliphaticAliphaticAliphatic
AlkanesAlkanesAlkanesAlkanes AlkynesAlkynesAlkynesAlkynesAlkenesAlkenesAlkenesAlkenes
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2.2-2.3 Chemical Bonding
Figure 2.3 – Valence bond picture for H2
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2.2-2.3 Chemical Bonding – Two Possibilities
Figure 2.5
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2.4 Molecular orbitals by combining two atomic orbitals
Figure 2.6
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2.5 Introduction to Alkanes – Methane, Ethane, Propane
Figure 2.7
CH4 CH3CH3 CH3CH2CH3
b.p. -160 oC -89 oC -42 oC
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2.6 sp3 Hybridization and bonding in Methane
Figure 2.9
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2.6 sp3 Hybridization and bonding in Methane
Figure 2.10
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2.7 sp3 Hybridization and bonding in Ethane
Figure 2.11
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2.8 Isomeric alkanes – the Butanes
Structural Isomers
C5H12
neopentane
C4H10 isobutane
C5H12
n-pentane
C5H12
isopentane
C4H10 n-butane
2.9-2.10 Higher alkanes – the C5H12 isomers
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2.10 Higher alkanes – diversity
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Careful with drawing chains!
CH3CHCH2CH3
CH3 CH3CHCH2CH3
CH3 CH3CH2CHCH3
CH3
CH3CH2CHCH3
CH3CH2CH2CH3
CH3
CH3
All the same compound
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2.11-2.12 Alkane nomenclature
Need to know up to C-12
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IUPAC Rules:
• Find the longest continuous carbon chain
• Identify substituent groups attached to the chain
• Number the chain so as to keep numbers small
• Write the name in the following format:
Numerical location - [substituent(s)][parent alkane]
e.g. 2,3-dimethylheptane
2.11-2.12 Alkane nomenclature
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2.12 IUPAC Rules and how to apply them
Hexane (IUPAC); n-hexane (common)
Longest chain - hexane
substituent - methyl
position on chain - 2
2-methylhexane not 5-methylhexane
2,4-dimethylheptane
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2.13 Alkyl groups
Replace -ane ending with -yl
H
C
H
C
C
C
H
C
C
C
C
C
primary (1o) secondary (2o) tertiary (3o)
propyl group isopropyl group t-Butyl group 1-methylethyl 1,1-dimethylethyl
CH3
C
CH3
H3CC
H
H
H
C
H
H
C
H
H
CH3CH2CH2
CH
CH3
CH3
(CH3)2CH (CH3)3C
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2.14 Highly branched alkanes
4-ethyloctane
4-ethyl-3-methyloctane
4-ethyl-3,5-dimethyloctane
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2.15 Cycloalkanes
1,1,3-trimethylcyclohexane
C(CH3)3
(1,1-dimethylethyl)cycloheptane
2-ethyl-1,1-dimethylcyclopentane
(notice the “di” is not involved in the
alphabetization)
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2.16 Sources of alkanes and cycloalkanes
Figure 2.12
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2.17 Physical properties
Figure 2.15
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2.17 Physical properties – branched alkanes
Figure 2.16
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2.18 Chemical properties of Alkanes
Alkane properties:
• Generally very insoluble in water (“greasy” or “oily”)
• Individual molecules interact via van der Waals forces
• These intermolecular forces decrease with branching
• Alkanes may be combusted in oxygen:
e.g. CH4 + 2O2 CO2 + 2H2O H = - 213 kcal
i.e combustion of hydrocarbons releases energy
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2.18 Heats of combustion – Figure 2.17
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2.19 Oxidation-Reduction in Organic Chemistry
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C CH
H
H
H
2.20 sp2 Hybridization in ethylene
Figure 2.18
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2.20 sp2 Hybridization in ethylene
Figure 2.19
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2.20 sp2 Hybridization in ethylene
Figure 2.20
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2.21 sp Hybridization in ethylene
Figure 2.21
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2.21 sp Hybridization in acetylene
Figure 2.22
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2.21 sp Hybridization in acetylene
Figure 2.23