Drill 1

NOMENCLATURE AND STRUCTURE WRITING OF HYDROCARBONS

Hydrocarbons are organic compounds which contain only carbon and hydrogen. The four classes of
hydrocarbons are alkanes, alkenes, alkynes and aromatics. Alkanes are saturated hydrocarbons. Each of
their carbon is bonded o four other atoms trough as single covalent bonds. Saturated in this context means
that each carbon atoms in the molecule has the maximum number of hydrogen atoms. Alkenes, alkynes
and aromatics are classified as unsaturated hydrocarbons. They have one or more multiple bonds in their
structure. Alkenes contain carbon-carbon double bonds while alkynes have carbon-carbon triple bonds.
Aromatics has benzene rings.

The International Union of Pure and Applied Chemistry (IUPAC) established an international standard in
naming organic compounds to facilitate communication.

NAMING ALKANES
The IUPAC name of an alkene with an unbranched chain of carbon atoms consists of two parts:
1) a prefix that shows the number of carbon atoms in chain and 2) the suffix -ane, which implies that the
compound is a saturated carbon. Rings are designated by the prefix “cyclo”. Table 1 shows the prefixes
used by alkanes containing 1 to10 carbon atoms.

Table 1. Prefixes used in the IUPAC system for 1 to 10 carbons in an alkane

# of carbon atoms Prefix # of carbon atoms Prefix
1 meth- 6 hex-
2 eth 7 hept-
3 prop- 8 oct-
4 but- 9 non-
5 pent- 10 dec-
Source: Introduction to General, Organic and Biochemistry (11th ed) by F. Bettelheim et. al.

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 In general, the base part of the name reflects the number of carbons in what you have assigned to be
the parent chain. The suffix of the name reflects the type(s) of functional group(s) present on (or within)
the parent chain.

Parent + Suffix
-ane for alkane
Number of carbon atoms in
-ene for alkene
the longest chain
-yne for alkyne

Other groups which are attached to the parent chain are called substituents. Alkyl groups as substituents
are named by replacing the “ane” ending in its alkane form with “yl”. Refer to figure below for the list of
some common alkyl groups.

Aside from alkyl groups, halogens and other groups can also be substituents.

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General Rules in Naming Alkanes

Example: Give the IUPAC name of the structure:

CH 2CH 2CH 3
it can also be drawn as
CH3CH2CH2CH2CHCH2CH3

(condensed structural formula) (skeletal structural formula)

1. Find the longest continuous chain of carbons in the molecule. The number of carbons in the
longest chain becomes the parent name.

2. After finding the parent chain, number the parent chain starting with the end nearest the first
substituent (remember: substituent is any fragment that juts off the main chain).

Correct Numbering Wrong Numbering

3. Next, determine the names of all substituents.

Alkyl with 2
carbon atoms
Parent chain with (ethyl)
8 carbon atoms
(octane)

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 4. For alkane with more than one substituents, put the substituents in alphabetical order (ie. ethyl
before methyl) in front of the parent name. The prefixes di, tri, tetra, etc., used to designate several
groups of the same, are not considered when alphabetizing.

5. Next, identify the positions of all substituents in the name by placing the carbon number where
the substituent attaches to the parent chain in front of it. For example, 2-methylheptane indicates
that a methyl substituent is attached to the number 2 carbon. Therefore,

IUPAC Name: 4-Ethyloctane

Examples:

3-Bromo-2-chloro-5-ethyl-4,4-dimethyloctane 3-Fluoro-4-isopropyl-2-methylheptane

General Rules in Naming Cycloalkanes

1. For a monosubstituted cycloalkane the ring supplies the root name and the substituent group is named
as usual. A location number is unnecessary.

2. If the alkyl substituent is large and/or complex, the ring may be named as a substituent group on an
alkane.

3. If two different substituents are present on the ring, they are listed in alphabetical order, and the first
cited substituent is assigned to carbon #1. The numbering of ring carbons then continues in a direction
(clockwise or counter-clockwise) that affords the second substituent the lower possible location
number.

4. If several substituents are present on the ring, they are listed in alphabetical order. Location numbers
are assigned to the substituents so that one of them is at carbon #1 and the other locations have the
lowest possible numbers, counting in either a clockwise or counter-clockwise direction.

5. The name is arranged, listing groups in alphabetical order and giving each group (if there are two or
more) a location number. The prefixes di, tri, tetra etc., used to designate several groups of the same
kind, are not considered when alphabetizing.

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 1-sec-butyl-3-nitrocyclohexane
(numbering determined by the
alphabetical order of substituents)

Examples:

1,3-Dimethylcyclohexane 1-Bromo-3-ethyl-5- 1-Bromo-2-

methylcyclohexane methylcyclobutane

General Rules in Naming Alkenes and Cycloalkenes

1. Number the chain of carbons that includes the C=C so that the C =C has the lower position number,
since it has a higher priority than any substituents

2. Change “ane” to “ene” and assign a position number to the first carbon of the C =C

3. In numbering, the parent chain must be numbered from the end nearest a double bond carbon atom.
If the double bond is in the center of the chain, the nearest substituent rule is used to determine the
end where numbering starts.

4. If more than one double bond is present the compound is named as a diene, triene or equivalent prefix
indicating the number of double bonds, and each double bond is assigned a locator number.

5. In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of the two is #1
may be determined by the nearest substituent rule.

4,4-Difluoro-3-methyl-1-butene 1,1-Difluoro-2-methylbuta-
or 1,3-diene 5-Methylcyclopenta-1,3-diene
4,4-Difluoro-3-methylbut-1-ene

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 2-Methyl-3-hexene 3-Methylcyclohexene 1,5-Dimethylcyclopentene
or
2-Methylhex-3-ene

General Rules in Naming Alkynes

1. Number the chain of carbons that includes the C≡C so that the C≡C has the lower position number,
since it has a higher priority than any substituents

2. Change “ane” to “yne” and assign a position number to the first carbon of the C≡C

3. In numbering, the parent chain must be numbered from the end nearest a triple bond carbon atom. If
the triple bond is in the center of the chain, the nearest substituent rule is used to determine the end
where numbering starts.

4. If several multiple bonds are present, each must be assigned a locator number. Double bonds precede
triple bonds in the IUPAC name, but the chain is numbered from the end nearest a multiple bond,
regardless of its nature.

5. Because the triple bond is linear, it can only be accommodated in rings larger than ten carbons. In
simple cycloalkynes the triple bond carbons are assigned ring locations #1 and #2. Which of the two is
#1 may be determined by the nearest substituent rule.

Pent-3-en-1-yne Pent-1-en-4-yne
4,4-difluoro-3-methyl-1-butyne (“yne” closer to end (“ene” and “yne” have equal
or of chain) priority unless they have the
4,4-Difluoro-3-methylbut-1-yne same position number, when
“ene” takes the lower number)

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DRAWING STRUCTURE OF ALKANES

To draw structures of alkanes, consider following the steps below:

Example: Draw the structure for butane

Step 1: Start by drawing the four (4) carbon atoms in a straight chain with all carbon atoms bonded
singularly.

−C−C−C−C−

Step 2: Add a single bond to all remaining spaces on the carbon atom such that each carbon atom has
four possible bonding sites.

Step 3: Add one hydrogen atom to the end of each of the single bonds formed in Step 2.

Therefore, the structure of butane is:

Line-bond structural formula of butane

OR

CH3CH2CH2CH3 Condensed structural formula of butane

OR

Skeletal structural formula of butane

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DRAWING STRUCTURE OF ALKENES

Drawing alkenes also follows the same rules as the alkanes. Remember to place the double bond where
the name indicated its placement.

Example: To draw the structure of 4-Methyl-2-heptene (or 4-methylhept-2-ene):

Therefore, the molecule has the structure:

DRAWING STRUCTURE OF ALKYNES

To draw alkynes, again follow the same rules as for alkanes and alkenes. Remember to place the triple
bond where the name indicated its placement.

Example: To draw the structure of 5-Ethyl-3-octyne (or 5-Ethyloct-3-yne):

Therefore, the molecule has the structure:

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References:

Bettelheim, F., Brown, W., Campbell, M. (2017) General, Organic, and Biological Chemistry, 11th ed.

McMurry, J. (2000) Organic Chemistry, 7th ed.

https://www.angelo.edu

https://www.vanderbilt.edu/AnS/Chemistry/Rizzo/

https://www.chem.fsu.edu/chemlab/chm1046course/hydrocarbons.html

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 Name: Score:

Section: Date:

Worksheet 1: Nomenclature and Structure Writing of Hydrocarbons

Write the IUPAC name of the following:

Structure IUPAC Name

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Draw the structure of the following (condensed or skeletal structure)

IUPAC Name Structure

4-Butyl-6-ethyl-2,5-dimethylnonane

2,3-Dimethylbutane

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 5,5-Diethyl-2,2,4,4-tetramethyloctane

3-Ethyl-3-methylhexane

1-Ethyl-3-t-butylcyclopentane

2-Methyl-1-pentene

3-Ethyl-3-methylhex-1-ene

1,5-Octadiene

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 3,3,4,4-Tetramethylcyclobutene

Hept-3-yne

3-Methyl-3-nitro-4-octyne

2,2,10-triiodo-5-methyl-3-decyne

8-Bromooct-3-yne

4-Isopropyl-2-heptyne

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