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Cycloalkanes
Key Questions
Saturated hydrocarbon
A hydrocarbon that contains only carboncarbon
single bonds
Unsaturated hydrocarbon
A hydrocarbon that contains one or more carbon
carbon double bonds, triple bonds, or benzene
rings
Aliphatic hydrocarbon
An alkane
Line-angle formula
An abbreviated way to draw structural formulas
in which each vertex and line terminus
represents a carbon atom and each line
represents a bond.
Butane, CH3CH2CH2CH3,
is the fuel in this lighter.
Butane molecules are
present in both the liquid
and gaseous states in the
lighter.
CH3(CH2)2CH3
Solution
(a) Each structural formula has an unbranched
chain of six carbons; they are identical and
represent the same compound.
Problem 2.2
Do the line-angle formulas in each of the
following sets represent the same compound or
constitutional isomers?
Problem 2.3
Draw structural formulas for the three
constitutional isomers with the molecular
formula C5H12.
Alkyl group
A group derived by removing a hydrogen from
an alkane; given the symbol RR A symbol used to represent an alkyl group
Solution
Problem 2.4
Write the molecular formula and IUPAC name
for each alkane.
B. Common Names
All alkanes with the molecular formula C4H10 are
called butanes, all those with the molecular
formula C5H12 are called pentanes, and all those
with the molecular formula C6H14 are called
hexanes.
For alkanes beyond propane, iso indicates that
one end of an otherwise unbranched chain
terminates in a (CH3)2CH- group
isopropylcyclopentane
1-tert-butyl-4-methylcyclohexane
A. Alkane
Conformation
Any three-dimensional arrangement of atoms in a molecule that
results from rotation about a single bond.
B. Cycloalkanes
Cyclopentane
Cyclohexane
Stereoisomers
Isomers that have the same connectivity of their atoms
but a different orientation of their atoms in space
Problem 2.7
Which of the following cycloalkanes show cis-trans isomerism? For each
that
does, draw both isomers.
(a) 1,3-Dimethylcyclopentane
(b) Ethylcyclopentane
(c) 1,3-Dimethylcyclohexane
Alkanes
What Are the Physical Properties of Alkanes?
A. Melting and Boiling Points
The boiling points of alkanes are lower than
those of almost any other type of compound
with the same molecular weight. In general,
both boiling and melting points of alkanes
increase with increasing molecular weight
B. Solubility: A Case of
Like Dissolves Like
C. Density
The average density of the
liquid alkanes is about 0.7
g/mL; that of highermolecular-weight alkanes
is about 0.8 g/mL.
All liquid and solid alkanes are less dense than
water (1.000 g/mL) and, because they are
insoluble in water, they float on water.
Problem 2.8
Arrange the alkanes in each set in order of
increasing boiling point.
(a) 2-Methylbutane, pentane, and 2,2dimethylpropane
(b) 3,3-Dimethylheptane, nonane, and 2,2,4trimethylhexane
Problem 2.9
Reaction of propane with chlorine gives two products, each
with the molecular formula C3H7Cl. Draw structural
formulas for these two compounds, and give each an IUPAC
name and a common name.
B. Solvents
Several low-molecular-weight haloalkanes are
excellent solvents in which to carry out organic
reactions and to use as cleaners and degreasers.
Carbon tetrachloride (carbon tet) was the first
of these compounds to find wide application, but
its use for this purpose has since been
discontinued because it is now known that
carbon tet is both toxic and a carcinogen. Today,
the most widely used haloalkane solvent is
dichloromethane, CH2Cl2.