carbon

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Chapter 12
Saturated Hydrocarbons - Alkanes
Hydrocarbons
• Compounds that contain only carbon and hydrogen
• Two classes: Aliphatic and aromatic
2
The Petroleum Feedstock
• Most alkanes come from petroleum
• Composed mostly of alkanes and aromatic
hydrocarbons
3
4
• Purification via fractional distillation
5
Physical Properties of Hydrocarbons
• Solubility:
– Tend to be insoluble in water
– Can be used for protective coatings
– Good preservative for reactive metals
• Density:
– Tend to have lower densities than water
• 0.6 g/mL – 0.8 g/mL
7
Boiling Points
• Boiling point: Temperature at
which liquid turns to vapor
– Temperature at which
vapor pressure of
substance = atmospheric
pressure
– B.P. of unbranched alkanes
increases by approx. 20 –
30 °C per carbon
9
Intermolecular Interactions for Alkanes
• Electron clouds can be temporarily distorted
10
Intermolecular Interactions for Alkanes
• Induced dipole
• van der Waals attraction (or a dispersion
interaction)
• Greater intermolecular forces = higher b.p.
11
Molecular Shape and Boiling Point
• Greater branching = lower b.p.
• Molecules that are spherical have less surface area
12
13
Melting Points
• Melting point: Temperature at which a
substance transforms from solid to liquid
• A narrow m.p. is an indicator of purity
• Branching interferes with crystal packing
leading to lower m.p. values
• Symmetric molecules tend to have unusually
high m.p’s
2.6 Physical Properties of Alkanes
14
Melting Points
• M.P. increases with number of carbons
15
Combustion
• Alkanes are the least reactive organic
compounds
• Alkanes react rapidly with O2 in combustion
• A commercially important reaction with
increasingly significant global impact
16
Unbranched Alkanes
• Referred to as normal or n-alkanes
• Possess a linear carbon chain
17
20
Formulas
Molecular
Formula
21
Problems
1) How many hydrogens does n-Octadecane,
an alkane containing 18 carbons, have?
2) Give the molecular, structural, condensed,
and skeletal formulas for n-Octadecane
3) Estimate the boiling point and density of nOctadecane
Isomers
• Compounds with the same molecular formula,
but different structural formula
• Constitutional Isomers/Structural Isomers:
compounds with the same molecular formula
but different atom connectivity
C4H10
23
Organic Nomenclature
• Standardized by International Union of Pure
and Applied Chemistry (IUPAC)
• The current system is called substitutive
nomenclature
• Rules for alkane nomenclature extend to most
other compound classes
• Apply the following rules:
24
Substitutive Nomenclature of Alkanes
1. Unbranched alkanes are named according to
number of carbons
2. If branched, find the longest continuous
carbon chain and identify this as the
principle/parent chain
25
Substitutive Nomenclature of Alkanes
3. If two chains are equal in length, select the
one with the most substituents
4. Number the principle chain, giving the lower
number to the first branching point
26
Substitutive Nomenclature of Alkanes
5. Identify the name of each branch and to
which carbon on the parent chain it is
attached
• Branching groups are called substituents
• Those derived from alkanes are alkyl groups
27
• Methyl group
• Attached to C3
3-methyl
6. Construct the name
a. Location of branch (3)
b. Name of branch (methyl)
•
Note: a hyphen goes between the location and
branch
c. Name of parent chain (hexane)
30
Problems
• Name the following molecules
7. When more than one of the same substituent
is present:
– Indicate which carbon each substituent is on
– Use Greek prefixes (di-, tri-, tetra-) to indicate how
many of each substituent you have
32
Substitutive Nomenclature of Alkanes
8. For multiple substituents, select the
numbering scheme that gives the smaller
number at first point of difference
33
9. Cite substituents in alphabetical order
regardless of location
• Di-, tri-, tetra-, and hyphenated prefixes tertand sec- are ignored
• Iso-, neo-, cyclo- are not ignored
34
Problems
• Name the following molecules:
• Draw 2-bromo-3-chloro-4-fluoro-2,3,4-trimethylheptane
36
10. If the numbering of different groups is not
resolved, the first-cited group gets the lowest
number
37
Highly Condensed Structures
• Highly condensed structures are commonly
used
38
Classification of Carbon Substitution
• Primary (1°) carbon: A carbon bonded to 1 other
carbon
• Secondary (2°) carbon: A carbon bonded to 2 other
carbons
• Tertiary (3°) carbon: A carbon bonded to 3 other
carbons
• Quaternary (4°) carbon: A carbon bonded to 4 other
carbons
39
Classification of Carbon Substitution
• Similarly, hydrogens may also be classified as
primary, secondary, tertiary, or quaternary
40
Problems
• Locate the primary, secondary, tertiary, and
quaternary carbons in the following molecule
Cycloalkanes
• Alkanes with closed loops or rings
• Add the prefix cyclo
• Note that cyclohexane has 2 fewer hydrogens
than hexane
42
Nomenclature of Cyloalkanes
• The same nomenclature rules are followed
• Do not forget the cyclo part of the name
• If the noncyclic carbon chain contains more carbons
than the ring, it is named as the parent chain
43
Problems
• Name the following compounds
44
45
Problems
•
Draw the following compounds
1) 1-chloro-4-ethylcyclohexane
2) 2-bromo-1,1-dimethylcyclobutane
3) 1,1,2,2-tetramethylcyclopropane
The “R” and “Ph” Notation
• A convenient way to represent a generic structure or
portion of a molecule
• R Notation: R represents all alkyl groups
• A Benzene ring may be called a “phenyl group” and
can be represented by Ph-
47
The “Ar” Notation
• Use Ar- for more highly substituted rings
48
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