Hydrocarbons- 1 -

SCH4U Name _____________________________ Date ____________________

Naming and Drawing Hydrocarbons

 The carbon atom forms the basis of ORGANIC COMPOUNDS
 The carbon atom has 4 valence electrons, therefore forms 4 covalent bonds
 Its ground state configuration is 1s22s22p2
 For a carbon atom with 4 single bonds, a “2s” electron gets promoted and the valence orbitals
undergo sp3 hybridization to form a tetrahedral arrangement

 Exceptions: compounds that contain carbon but are considered to be INORGANIC are:
CO2, CO, compounds containing CO32- or CN-

 Hydrocarbons are organic compounds that contain only carbon and hydrogen atoms

HYDROCARBONS

Aliphatic Aromatic (Arenes)

Contain only regular single, double, Contain the benzene ring (with bonds of
and triple bonds delocalized pi electrons

Acyclic Cyclic
Carbons are bonded in an open-chain Carbons form a ring structure
structure

Alkanes Cycloalkanes
Only C-C single bonds Only C-C single bonds in the ring
E.g. butane E.g. cyclobutane

Alkenes Cycloalkenes
At least one C=C double bond At least one C=C double bond in the ring
E.g. butene E.g. cyclobutene

Alkynes
At least one CC triple bond
E.g. butyne
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NAMING AND DRAWING ALKANES

Example:
NAME MOLECULAR FULL STRUCTURAL CONDENSED LINE
FORMULA DIAGRAM/FORMULA STRUCTURAL DRAWING
FORMULA

MOLECULAR
PREFIXES INDICATE THE NUMBER OF
MODEL
CARBON ATOMS
meth- 1 hex- 6
eth- 2 hept- 7
prop- 3 oct- 8
but- 4 non- 9
pent- 5 dec- 10

 A homologous series is a series of compounds of the same family (with the same general formula)
which differ from each other by a common structural unit
 For example: the alkanes
Methane, CH4
Ethane, CH3CH3
Propane, CH3CH2CH3
Butane, CH3CH2CH2CH3
Etc.

PRACTICE PROBLEM #1:

MOLECULAR
NAME CONDENSED DIAGRAM LINE DRAWING
FORMULA

a propane C3H8 CH3CH2CH3

CH3CH2CH2CH2CH2CH2CH3
b Heptane C7H16 Or
CH3(CH2)5CH3
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IMPORTANT NOTE: A continuous chain of carbons is not always drawn in a

straight line!!

For example: and

are the SAME compound -- hexane

 But, , , is NOT the same compound as the two above, even

though it also has six carbon atoms!! The six carbon atoms in this compound are not in a continuous
chain. Instead, there is a five-carbon continuous chain with a one-carbon branch. This is called a
BRANCHED ALKANE.
 The name of this compound is 2-methylpentane

RULES FOR NAMING BRANCHED ALKANES:

Rule #1: Locate the longest continuous chain of carbon atoms (this is not
necessarily drawn in a straight line!!) This is the PARENT CHAIN. Name the parent
chain.
Rule #2: Locate the BRANCHES. Name the branches according to how many carbon
atoms they contain (e.g. methyl-, ethyl-, propyl-, etc.).
Rule #3: Number the carbon atoms of the parent chain so that the branches are
attached to the LOWEST numbered carbon atoms. (This may mean numbering the
parent chain from right to left instead of from left to right!)
Rule #4: If there is more than one of a particular type of branch (e.g. three methyl
branches), use the prefixes di-, tri-, tetra-, penta-, etc.
Rule #5: List the branches in alphabetical order before the parent name.

PRACTICE PROBLEM #2: Name each of the following.

a) b)

3-ethylhexane 3,5-dimethylheptane
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NAMING AND DRAWING CYCLOALKANES

PRACTICE PROBLEM #3: Name the following cycloalkanes.

a) b)

Cycloctane propylcyclopentane

NAMING AND DRAWING ALKENES AND ALKYNES

 Carbon atoms with one double bond and two single bonds (i.e. 3 sigma and 1 pi bond) are sp2-hybridized
 Carbon atoms with one triple bond and one single bond (i.e. 2 sigma and 2 pi bonds) are sp-hybridized

ADDITIONAL RULES FOR NAMING ALKENES AND ALKYNES

Rule #1: The chain chosen as the parent chain must contain the C=C double bond
or CC triple bond. (This may not be the longest continuous chain of carbons.)
Rule #2: The parent chain must be numbered to give the C=C double bond or CC
triple bond the lowest possible number.
Rule #3: The name of the alkene/alkyne must contain a number to indicate the
position of the double or triple bond.

PRACTICE PROBLEM #4:

a) b)

butene or 1-butene or but-1-ene 2-butene or but-2-ene

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GENERAL FORMULAS:

Alkanes CnH2n+2 e.g. butane C4H10

Alkenes and cycloalkanes CnH2n e.g. butene C4H8 and cyclobutane C4H8

Alkynes and cycloalkenes CnH2n-2 e.g. butyne C4H6 and cyclobutene C4H6

Starting from the general formula for an alkane, CnH2n+2, each additional bond
between carbons and each additional ring, decreases the number of hydrogen atoms
by 2.

PRACTICE PROBLEM #5: Name each of the following.

a) b)

4-propyloctane 2-methylpropane

c) d)

3,3-dimethyl-6-propylnonane 4-ethyl-5-isopropyl-2-methylheptane
or 3,4-diethyl-2,6-dimethylheptane
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e) f)

2,3,4-trimethylheptane 4-ethyl-1,2-dimethylcylcopentane

g) h)

4,4-diethyl-2-hexene 3,4-dimethylcyclopentene

i) j) CH3

CH3–CHCH–CH–CHCH–CH2

CH2CH3

6-methyl-4-propyl-2-heptyne 4-methyl-2,5-nonadiene

PRACTICE PROBLEM #6: Draw the condensed structural diagram and line diagram for each of
the following.
Note: line diagrams can be zig-zag at each carbon (unlike some of them shown here).
a) 5-ethyl-3,3-dimethylnonane
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b) 2,2,3,3-tetramethylpentane

c) 3-ethylcyclopentene

d) 4,4-dimethyl-2-pentyne

e) 6-ethyl-2,4-octadiene

PRACTICE PROBLEM #7: Determine the molecular formulas for the following compounds
without drawing the structures.

a) 5-butyl-3,4-diethyl-2,5,7-trimethylnonane general formula: CnH2n+2

number of carbons: 4 + 2(2) + 3(1) + 9 = 20 C20H42

b) 2,2-dimethyl-1,3,5-tripropylcycloheptane general formula: CnH2n

number of carbons: 2(1) + 3(3) + 7 = 18 C18H36

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STRUCTURAL ISOMERS

 Two or more compounds with the same molecular formula but different arrangement of atoms
(hence, different names)
 Example #1:

 Example #2: pentene, cyclobutane, and methylcyclobutane

PRACTICE PROBLEM #8: Draw and name as many structural isomers as possible with the
formula, C5H12.

pentane
2-methylbutane
2,2-dimethylpropane
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GEOMETRIC ISOMERS
 Unlike C-C single bonds, there is no rotation around a C=C double bond
 Therefore geometric isomers (or cis-trans) isomers are possible
 E.g. consider 2-butene
 In cis-2-butene, the two methyl groups attached to the double-bonded carbons are on the
SAME side

 In trans-2-butene, the two methyl groups attached to the double-bonded carbons are on
OPPOSITE sides

 Can the following molecule exist as cis and trans isomers?

PRACTICE PROBLEM #9: Name each of the following.

a) b) H

cis-3-hexene trans-3-heptene