Key

Name: ___________________________________________________________ Period: _________

Lecture 47
The Basics of Organic Nomenclature
Student Notes

Learning Objective(s)
• Use the International Union of Pure and Applied Chemistry (IUPAC) guidelines to write systematic names for
alkanes, alkenes, alkynes, and cycloalkanes with substituents

Alkanes

only
Alkanes are hydrocarbons that contain ________
single
__________ bonds
__________. They are often referred to as
saturated _____________________because
hydrocarbon
hydrogen
______________ they
are saturated (loaded to capacity) with ____________.

Alkanes often have the generic formula C nH2n+2

straight
Alkanes that contain four or more carbons may be _____________
chained
_____________or branched
_______________.

normal
The straight chain isomers are often referred to as the ____________
____________, or _______________.
alkane n-alkane

(n-pentane)
As the number of carbon atoms increases in the n-alkanes,
boiling
their _____________ point ________________.
_________ increases

The increase in boiling point is due to the

increase in ______________
__________________ force
dispersion _________that
comes with the increased number of electrons.

Methane, ethane, propane and butane are all gases at

room temperature and often used as heating or cooking
fuel. The next alkanes in the series are liquids at room
temperature and are all components of gasoline.
 n-alkanes (straight
chain alkanes) are
names according to the
meth- hept-
number
_____________
______________
of carbons with eth- Oct-
the suffix _________
-
ane

added to the end of prop-

non-

each name to classify

but- dec-
the molecule as an
alkane under-
pent-

nex- dodec-

Alkyl Substituents

Groups of carbon atoms branching off the base chain are __________
alky ___________and
groups are named as substituents. A
substituent
___________________ substituted _______
is an atom or group of atoms that has been _________________ hydrogen
for a______________
atom
________in an organic compound. Common alkyl groups are shown in the table below.

Halogen
Substituents
fluoro-
halogens
The _____________
Chloro-
can also be
substituents in bromo-
organic compounds
iodo-

Naming Alkanes

We will use the nomenclature system recommended by the International Union of Pure and Applied Chemistry (IUPAC)
which is used throughout the world.

longest ______________
1. Find the ____________ continuous__________ chain
carbon _________in the molecule and use the name of that chain as
the parent name. Note: the longest chain may not always be obvious and you may have to turn corners
2. Number the atoms in the main chain. Begin with number 1 nearest the first substituent.

3. Assign a number to each substituent to specify its point of attachment to the main chain. If there are two
substituents on the same carbon, assign them the same number.

4. Write the name as a single word. Use hyphens to separate prefixes and commas to separate numbers. If there is more
than one substituent, put them in _________________ order
alphabetical __________. If there are two or more identical substituents,
use prefixes (di, tri, tetra) as a multiplier.
 For each of the 12 alkanes shown below, write the IUPAC name for the structure
methyl methyl

81 6 54 32 I I 23 4 5 6 7

octane ethy/
3-methyl
4-ethyl-3-methyl heptane
etht
metht

I 2 3 4 5
I 2 3 4 S 6 7

methyl methyl
eth+

3 , 3, 5-trimethyl heptane
,3
3
-

diethylpentance

2 I
Propyl

123 4 S 6 7 8 methyl

3
methyl 4

2-methyl butane
3-methyl-5-propyloctane

methel methyl
10 987 O

ethyl 12 345 67 8

123 5
4
methyl methyl methyl methyl

5,
, 3, 4
2 , 6-pentamethyloctane
5 ethyl-5-methyl decane

bromo O
chloro
fluoro ethyl
I

I 5 4 methyl
23 5432
I methyl
3 2
4
methyl 7
Chloro I
butane
1-bromo-2-methyl 3 , 4-dichloro-2-fluorohexane
L

methyl
ethyl-2 , 4-dimethylheptane
methyl
4
24
.
5
I 3
ethyl 3-ethyl-2 , 2-dimethylpentance
 Alkenes

at least one
Alkenes are hydrocarbons with _____________ _____
__________ bond
double ________between carbon atoms.

Alkenes often have the generic formula CnH2n.

Note: There is only one way to place the double bond in ethene
and propene. In compounds with 4 or more carbons, the
placement of the double bond must be indicated.
Is But-3-ene possible?
No .
Following IUPAC rules "but-3-ene"
would be correctly named as but-1-ene
.

Alkynes

Alkynes contain at least one triple bond.

Alkenes and alkynes have fewer hydrogen atoms than their

corresponding alkanes and are therefore called
unsaturated ____________________because
__________________ hydrocarbons they are
not loaded to capacity with hydrogen atoms.

Alkynes often have the generic formula C nH2n-2.

Just as with alkenes, the placement of the triple bond must be

specified when there is a 4+ carbon chain

Naming Alkenes and Alkynes

Alkenes and alkynes are named in the same way as alkanes with the following exceptions:

contains ______
• The base chain is the longest continuous carbon chain that ______________ double ____
the __________ triple
or __________
bond
_________.
• The base name has the suffix -ene for alkenes and -yne for alkynes

• The chain is numbered to give the double or triple bond the lowest possible number. (NOT SUBSTITUENTS!!)

• The number location of the double or triple bond is inserted before the suffix

IMPORTANT NOTE: You will encounter two ways of

inserting the number to indicate the location of the
5 4321 double or triple bond.

1.The number is inserted just before the base name: 2-

Pentyne
2.The number is inserted just before the suffix: Pent-2-
What is the IUPAC name for the compound above? yne

pent-2-yne The second version is the official IUPAC method, and

we will stick to that method
 For each of the 8 unsaturated hydrocarbons shown below, write the IUPAC name for the structure

5 3 I I 3 5
7 7
2 4 U

U 4 2
methyl methyl

kept-3-ene
2
, 6-dimethyl hept-3-ene

ethyl
I
2 ethyl
2 l
8
I 34 4
5 T
3
methyl
6
S
4- ethyl-3-methyloct-4-ene
S
4 -

ethy/non-3-ene'
9

S
4
L 3
3 I
I 4
2 5 7 9 1

2
12
C G 18
nex-3-yue
dodec-4-yne

I I
4 6 4
2 3
2
3
5 5

methyl ethy

3-ethylhex-1-yne
3-methyl pent-1-yne
 Cycloalkanes

saturated hydrocarbons
cyclic
______________ __________ ___________________are called cycloalkanes. In skeletal drawings, they are represented
polygons
by ________________.

To name cycloalkanes:

1. Count the number of carbons in the ring and add the

prefix cyclo-
_______________________to the base alkane.
2. If there are substituents, start numbering the carbons at the
point of attachment.

3. If there is more than one substituent, begin numbering at

alphabetical
the group with ___________________ priority and
_____________
proceed around the ring in the direction that gives the
second substituent the lowest possible number.
methyl
Important Note: -

propyl
4
If there is an alkyl substituent on a cycloalkane and it has 3 5
the same or more carbons than the cycloalkane, then the
cycloalkane is the substituent. 2
I

* butyl

What is the IUPAC name of the compound shown

above?

1-butyl-3 , 3-dimethyl-5-propylcyclohexane

For each of the 6 cycloalkanes shown below, write the IUPAC name for the structure
* Chloro
*
methyl
bromo
I methyl butyl
2 2
I
3
8 3
8 ethy14 &
6

4
7 4
7
3 7

I 5 5 6 methyl methyl
2 S
Chloro
fluoro I
* ethyl 9

1, 5-dichloro-3-methyl
cyclooctane
1, 1-dibromo-3-butyl-5-fluoro-7-methylcyclo octane

*
1 , 3-diethyl-5 7-dimethyl,
methyl
propyl Cyclononane
I

ethyl
Methyl
& 2
I
propul 2
D
H 3 propyl 3 4
32

propyl
1,
1- dimethylpropA Y 1-ethyl-1 , 3, 3-tripropyl 1-ethyl-2, 2 , 3 ,
3-tetramethyl
cyclopropane
cyclobutane
 Write the structural formula for each of the following organic compounds from their IUPAC names
2-methylbutane 3,3-dimethylpentane 2,3,4-trimethyloctane
H
H
H I

C H -
C H
It I H -
-
H H -
H
I H -
C -
H H I 1 ↓

H C H &

4 -
C H
-
- - -

H I C C

-
H H H
-

H H
-

& I
H I It I I I I
H I
I
C- H H -
C -
C -
C- C -
C-H C -
H H
C H
- -

C -
c -
I I
it
I I
H
-
I
I
H ↓ H H
H C
I H H
H
-

H H -

It
C
-
H
H -

H
I
I
I
H
C - C - H
H -

H
I
H

2,4-dimethyl-4-ethylheptane 1,3-dipropylcyclohexane 3-methylhex-3-ene

H
H H
It
CHH)
H I H H I
&

H
C H
C H
-

It
-

H C H
-

H H
-

H
- -y HH
- -

H
H
I I
&
- -H &
I I
I I C - I
H L +H
-
I
H C c c c C C H
- C H
- -

=
-

c
- - -
-
-

c
C
H
-

1
-

H
H H it H
-

it
HH !
I
I
= I
H H
H C
-
-

C
-

H -

in I H'
I+ -
C
-
H H-h &
c
H HH
C -
-
C H
H
-

HF
#

2,6-dimethylhept-3-yne 3-methylcyclobutene 7-ethyl-2,2-dimethyl-4-propylnonane

H
Y I HHH
H ↑

HH C-
HH
C H
C
-

I H
-

C
-
-

H c
-

H
HH C H
- -

I I
H H
- -

I I
H H H
cc
-
I
H
- -

CEC -
C -
-- C H -

C I &

CH
C
-
- I

it c
I
C
it H it H C c
- - -
-

1
-

I
H H
-

I
I
H
I H H I
H C -

C H
H
H 2 H
- - -

C
-
-

H
-
-

H H H
H H
I
I
H

+
C
-

C -

C S

"
H -

H H -
-
H

H-