Organic Compounds
Nomenclature, Physical
Properties, and
Representation of
Structure
Introduction
• Alkanes is a hydrocarbon that contains only single
bonds.
• Compounds that contain only carbon and hydrogen
are called hydrocarbons.
• General formula: CnH2n+2
• The names of several straight-chain alkanes are
given in table 2.1
3
4
Constitutional isomers
• Their molecules have different constitutions.
• iso-, which stands for isomer, is commonly given to 2-
methyl alkanes.
• In other words, if there is methyl group located on the
second carbon of a carbon chain.
• Number of constitutional isomers increases rapidly as the
number of carbons in an alkanes increases.
• Method of nomenclature is called systematic
nomenclature (IUPAC nomenclature)
Nomenclature of Alkyl Substituents
• Removing a hydrogen from an alkane results in an alkyl substituent.
• Replacing the “ane” ending of alkane with “yl”.
• Letter ”R” is used to indicate any alkyl group.
• If a hydrogen is replaced by an OH, the compound becomes
an alcohol.
• If it is replaced by an NH2, the compound becomes an
amine.
• if it is replaced by a halogen, the compound becomes an alkyl
halide.
• If it is replaced by an OR, the compound becomes an ether.
Different Kinds of Carbons and Hydrogens
• There are four alkyl groups that contain four
carbon atoms.
• sec-butyl group, bonded to two other carbon
atoms.
• tert-butyl group, bonded to three other carbon
atoms.
The use of an “iso” prefix and some common
alkyl group names
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Nomenclature of Alkanes
• (1) Determine the number of carbons in the longest
continuous chain.
• (2) Number the chain so that the substituent gets the lowest
number.
• (3) Number the substituents to yield the lowest
possible number in the number of the compound
substituents are listed in
alphabetical order
The prefixes “di”, “tri”, “tetra’, “sec” and “tert” are ignored in alphabetizing12
substituent groups. But the prefixes ‘iso’ and ‘cyclo’ are not ignored.
• (4) Assign the lowest possible numbers to all of the
substituents
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• (5) If the same substituent numbers are obtained in both
directions, the first group cited receives the lower
number (lower number for first substituent)
• (6) If a compound has two or more chains of the same
length, the parent hydrocarbon is the chain with the greatest
number of substituents (more substituents preferred)
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• (7) Certain common nomenclatures are used in the
IUPAC system
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Nomenclature of Cycloalkanes
• (1) No number is needed for a single substituent on a ring
(the chain with higher number of carbon atoms is the parent hydrocarbon)
• (2) Name the two substituents in alphabetical order
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• (3) If there are more than two substituents, they are
cited in alphabetical order
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Nomenclature of Alkyl Halides (R-X)
In the IUPAC system, alkyl halides are named as substituted alkanes
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Nomenclature of Ethers (R-O-R)
As
substituents:
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Nomenclature of Alcohols (R-OH)
• In an alcohol, the OH is a functional group
•A functional group is the center of reactivity in a molecule
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• (1) Determine the longest hydrocarbon containing the
functional group:
• (2) The functional group suffix should get the lowest number
hexane-2,4-diol
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• (3) When there is both a functional group suffix and a
substituent, the functional group suffix gets the lowest
number:
• (4) The chain is numbered in the direction that gives a substituent the
lowest number
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• (5) The functional group substituent on a ring gets the
number 1, but the functional group is not numbered in
the name
CH3 HO CH3 OH
CH3
CH3
OH
3-methylcyclohexanol 1-methylcyclohexanol 2, 2-dimethylcyclopentanol
not not not
3-methylcyclohexan-1-ol 1-methylcyclohexan-1-ol 2, 2-dimethylcyclopentan-1-ol
• (6) If there is more than one substituent, the substituents are cited in
alphabetical order
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Nomenclature of Amines
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(The prefix N indicates that the group (alkyl) is bonded to a nitrogen rather than a carbon)
The substituents are listed in alphabetical order and a number or an “N” is
assigned to each one:
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Physical properties
• Boiling Points
• Melting Points
• Solubility
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Boiling points
• Boiling point of a compound is the temperature at which the
liquid form of the compound becomes a gas.
• Compound to vaporize- the forces that hold the individual
molecules close to each other in the liquid must be overcome.
• Boiling point of a compound depends on the strength of the
attractive forces between the individual molecules.
• If the molecules are held together by strong forces- it will take
a lot of energy to pull the molecules away to each other- the
compound will have a high boiling point.
• In contrast….
• Alkanes are held together by these van der Waals Forces
(the weakest among all the intermolecular attractions)
The boiling point of a compound increases with the increase in van der Waals
force (induced-dipole-induced-dipole interactions (non-polar molecules)
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• Dipole–Dipole Interaction
Dipole–dipole interactions (polar molecules) are stronger than van der Waals force
but weaker than ionic or covalent bonds
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Hydrogen bonds are stronger than another dipole-dipole
interactions and van der Waals force
Hydrogen bond:
A special kind of dipole-dipole
interaction that occurs between a
hydrogen atom that is bonded to an
oxygen, nitrogen, or fluorine and the
lone-pair electrons of an oxygen,
nitrogen, or fluorine in another
molecule.
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Ethers – boiling points generally higher than alkanes of comparable molecular weight
(both van der Waals and dipole-dipole interactions are involved in ethers compared to
only van der Waals in alkanes)
Alcohols – boiling points for alcohols are higher than ethers as, in addition to van der
Waals and dipole-dipole interactions, hydrogen bonds are found in alcohols
Amines – lower boiling points than alcohols because the hydrogen bonds in amines
are weaker than those of alcohols due to the less electronegativity of nitrogen (in
amines) compared to oxygen (in alcohols)
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Both van der Waals forces and dipole-dipole interactions must
be overcome for an alkyl halide to boil
Size of halogen (Y) atom : H < F < Cl < Br < I
The larger the atom, the more loosely it holds the outermost electrons, and the more
they can be distorted to create a strong induced dipole (higher polarizability) –
higher boiling point.
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Melting point
• Melting point is the temperature at which a solid is
converted into a liquid.
• In table 2.1- you will see that the melting points increase
as molecular weight increases.
Solubility
• Polar compound dissolves in polar solvent (like dissolve like)
•Nonpolar compound dissolves in nonpolar solvent (like
dissolve like)
Clustering of the solvent
molecules around the polar
molecules separates them
from each other, which is
what makes them dissolves.
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Conformations of Alkanes:
Rotation about Carbon–Carbon Bonds
Recall ….
Conformations: A carbon-carbon
The different spatial single bond (a σ
arrangements of the atoms bond) is formed
that result from rotation about when an sp3 orbital
a single bond. of one carbon
Conformational overlaps an sp3
isomers/conformers: orbital of another
Molecules with different carbon.
conformations.
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Different Conformations of Ethane
Rotation about a C-C bond is not completely free due to the energy barrier. For ethane,
however, the energy barrier is small enough (2.9 kcal/mol or 12 kJ/mol) to allow
continuous rotation.
A staggered conformation is more stable (lower potential energy) than a eclipsed
conformation. 37
Cycloalkanes: Ring Strain
• Angle strain results when bond angles deviate from the
ideal 109.5° bond angle
sp3-sp3
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The chair conformation of cyclohexane is free of strain - bond
angles are 111°, which is close to the ideal tetrahedral bond
angle of 109.5°. All adjacent bonds are staggered.
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Ring Flipping (ring interconversion) in Cyclohexane
Before Ring Flip (left):
Axial (red) bonds are vertical and alternate above and below the ring.
Equatorial (blue) bonds point outward from the ring.
After Ring Flip (right):
Axial bonds (before ring flip) now become equatorial bonds.
Equatorial bonds (before ring flip) now become axial bonds. 40
The Conformations of Cyclohexane
and Their Energies
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