Naming of Organic

Compounds
***continuation
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How To NAME Alkyl Halides
• Alkanes bearing halogen substituents are named in the IUPAC substitutive
system as haloalkane:
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• When the parent chain has both a halo and an alkyl substituent attached to it,
number the chain from the end nearer the first substituent, regardless of whether
it is halo or alkyl.
• If two substituents are at equal distance from the end of the chain, then number
the chain from the end nearer the substituent that has alphabetical precedence
4 • Common names for many simple haloalkanes are still widely used, however. In
this common nomenclature system, called functional class nomenclature,
haloalkanes are named as alkyl halides. (The following names are also accepted
by IUPAC).
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How To Name Alcohols
• In IUPAC substitutive nomenclature a name may have as many as four features:
locants, prefixes, parent compound, and suffixes. Consider the following
example:
6 The following procedure should be followed in
giving alcohols IUPAC substitutive names:
1. Select the longest continuous carbon chain to which the hydroxyl is directly
attached. Change the name of the alkane corresponding to this chain by
dropping the final -e and adding the suffix -ol.
2. Number the longest continuous carbon chain so as to give the carbon atom
bearing the hydroxyl group the lower number. Indicate the position of the
hydroxyl group by using this number as a locant; indicate the positions of
other substituents (as prefixes) by using the numbers corresponding to their
positions along the carbon chain as locants.
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4-Methyl-1-pentanol
1-Propanol 2-Butanol or 4-methylpentan-1-ol
(not 2-methyl-5-pentanol)

3-Chloro-1-propanol 4,4-Dimethyl-2-pentanol
or 3-chloropropan-1-o or 4,4-dimethylpentan-2-ol
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Alcohols containing two hydroxyl groups are commonly called glycols. In the IUPAC
substitutive system they are named as diols:
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How To NAME cycloalkanes
• How To Name Monocyclic Cycloalkanes
• Cycloalkanes are named by adding “cyclo” before the parent name
1. 1. Cycloalkanes with one ring and no substituents: Count the number of carbon
atoms in the ring, then add “cyclo” to the beginning of the name of the alkane with
that number of carbons. For example, cyclopropane has three carbons and
cyclopentane has five carbons
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2. Cycloalkanes with one ring and one substituent: Add the name of the
substituent to the beginning of the parent name. For example, cyclohexane with an
attached isopropyl group is isopropylcyclohexane. For compounds with only one
substituent, it is not necessary to specify a number (locant) for the carbon bearing
the substituent
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3. Cycloalkanes with one ring and two or more substituents: For a ring with two
substituents, begin by numbering the carbons in the ring, starting at the carbon
with the substituent that is first in the alphabet and number in the direction that
gives the next substituent the lower number possible. When there are three or
more substituents, begin at the substituent that leads to the lowest set of numbers
(locants). The substituents are listed in alphabetical order, not according to the
number of their carbon atom.
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4. When a single ring system is attached to a single chain with a greater number of
carbon atoms, or when more than one ring system is attached to a single chain,
then it is appropriate to name the compounds as cycloalkylalkanes. For example,
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How To Name Bicyclic Cycloalkanes
1. We name compounds containing two fused or bridged rings as bicycloalkanes
and we use the name of the alkane corresponding to the total number of
carbon atoms in the rings as the parent name. The following compound, for
example, contains seven carbon atoms and is, therefore, a bicycloheptane. The
carbon atoms common to both rings are called bridgeheads, and each bond, or
each chain of atoms connecting the bridgehead atoms, is called a bridge.
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2. We then interpose an expression in brackets within the name that denotes the
number of carbon atoms in each bridge (in order of decreasing length). Fused rings
have zero carbons in their bridge. For example
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3. In bicycloalkanes with substituents, we number the bridged ring system
beginning at one bridgehead, proceeding first along the longest bridge to the other
bridgehead, then along the next longest bridge back to the first bridgehead; the
shortest bridge is numbered last.
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How To Name Alkenes and Cycloalkenes
• The IUPAC rules for naming alkenes are similar in many respects to those for
naming alkanes:
• 1. Determine the parent name by selecting the longest chain that contains the
double bond and change the ending of the name of the alkane of identical length
from -ane to -ene. Thus, if the longest chain contains five carbon atoms, the
parent name for the alkene is pentene; if it contains six carbon atoms, the parent
name is hexene, and so on.
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2. Number the chain so as to include both carbon atoms of the double bond, and
begin numbering at the end of the chain nearer the double bond. Designate the
location of the double bond by using the number of the first atom of the double
bond as a prefix. The locant for the alkene suffix may precede the parent name or
be placed immediately before the suffix. We will show examples of both styles:
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3. Indicate the locations of the substituent groups by the numbers of the carbon
atoms to which they are attached:
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4. Number substituted cycloalkenes in the way that gives the carbon atoms of the
double bond the 1 and 2 positions and that also gives the substituent groups the
lower numbers at the first point of difference. With substituted cycloalkenes it is
not necessary to specify the position of the double bond since it will always begin
with C1 and C2. The two examples shown here illustrate the application of these
rules:
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5. Name compounds containing a double bond and an alcohol group as alkenols
(or cycloalkenols) and give the alcohol carbon the lower number:
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6. If two identical or substantial groups are on the same side of the double bond,
the compound can be designated cis; if they are on opposite sides it can be
designated trans:
22 How To name alkynes
• Alkynes are named in much the same way as alkenes. Unbranched alkynes, for
example, are named by replacing the -ane of the name of the corresponding
alkane with the ending -yne. The chain is numbered to give the carbon atoms of
the triple bond the lower possible numbers. The lower number of the two carbon
atoms of the triple bond is used to designate the location of the triple bond.
When double and triple bonds are present, the direction of numbering is chosen
so as to give the lowest overall set of locants. In the face of equivalent options,
then preference is given to assigning lowest numbers to the double bonds. The
IUPAC names of three unbranched alkynes are shown here:
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The locations of substituent groups of branched alkynes and substituted alkynes
are also indicated with numbers. An −OH group has priority over the triple bond
when numbering the chain of an alkynol: