1.

Alcanos

Hidrocarburos
Son compuestos formados
exclusivamente por carbono e hidrgeno.

Alcanos
Los alcanos son hidrocarburos saturados, estn
formados exclusivamente por carbono e
hidrgeno y nicamente hay enlaces sencillos
en su estructura.

Frmula general: CnH2n+2 donde n

represente el nmero de carbonos del alcano.
Esta frmula nos permite calcular la frmula
molecular de un alcano. Por ejemplo para el
alcano de 5 carbonos: C5H [(2 x 5) +2] = C5H12

 Hidrocarburos.
Molculas que contienen slo hidrgeno y carbono
(CxHy)

Familias de hidrocarburos:
ACCLICOS
HIDROCARBUROS

ALIFTICOS
(ALICCLICOS)

CCLICOS
CARBOCCLICOS

Hidrocarburos acclicos
Alcanos: CnH2n+2 (enlaces )
Alquenos: CnH2n (enlaces )
Alquinos: CnH2n-2 (enlaces )

AROMTICOS

Hidrocarburos alicclicos
Cicloalcanos
Cicloalquenos
Cicloalquinos

Alcanos

Propiedades de los Alcanos

El estado fsico de los 4 primeros alcanos:
metano, etano, propano y butano es gaseoso.
Del pentano al hexadecano (16 tomos de
carbono) son lquidos y a partir de heptadecano
(17 tomos de carbono) son slidos.
El punto de fusin, de ebullicin y la densidad
aumentan conforme aumenta el nmero de
tomos de carbono.
Son insolubles en agua

Propiedades de los Alcanos

Pueden emplearse como disolventes para
sustancias poco polares como grasas, aceites y
ceras.
El gas de uso domstico es una mezcla de alcanos,
principalmente propano.
El gas de los encendedores es butano.

El principal uso de los alcanos es como

combustibles debido a la gran cantidad de calor
que se libera en esta reaccin.

Alkanes
Nomenclature:
The name of every organic molecule has 3 parts:
1. The parent name indicates the number of carbons in
the longest continuous chain.

2. The suffix indicates what functional group is present.

3. The prefix tells us the identity, location, and number of
substituents attached to the carbon chain.

Alkanes
Nomenclature:
The carbon substituents bonded to a long carbon
chain are called alkyl groups.
An alkyl group is formed by removing one H atom from
an alkane.
To name an alkyl group, change the ane ending of the
parent alkane to yl. Thus, methane (CH4) becomes
methyl (CH3-) and ethane (CH3CH3) becomes ethyl
(CH3CH2-).

Alkanes
Nomenclature:
Naming three- or four-carbon alkyl groups is more
complicated because the substituent can have isomeric
forms. For example, propane has both 1 and 2 H
atoms, and removal of each of these H atoms forms a
different alkyl group with a different name, propyl or
isopropyl.

10

Alkanes
Rule 1:
1. Find the parent carbon chain and add the suffix.

The parent is the longest continuous chain of carbon atoms.

11

Alkanes
Nomenclature:
Note that if there are two chains of equal length, pick the
chain with more substituents to simplify naming. In the
following example, two different chains in the same
alkane have seven C atoms. We circle the longest
continuous chain as shown in the diagram on the left,
since this results in the greater number of substituents.

12

Alkanes
Rule 2:
2. Number the atoms in the carbon chain from the end
that gives the first substituent the lowest number.

13

Alkanes
Nomenclature:
If the first substituent is the same distance from both
ends, number the chain to give the second substituent
the lower number.

14

Alkanes
Nomenclature:
When numbering a carbon chain results in the same
numbers from either end of the chain, assign the lower
number alphabetically to the first substituent.

15

Alkanes
Rule 3:
3. Name and number the substituents.
Name the substituents as alkyl groups.
Every carbon is part of the longest chain or a part of a
substituent, not both.
Each substituent needs its own number.
If two or more identical substituents are bonded to the
longest chain, use prefixes to indicate how many: di- for
two groups, tri- for three groups, tetra- for four groups,
etc.

16

Alkanes
4. Finally, write the name.
Substituent names and numbers come before the
parent.
List substituents in alphabetical order, ignoring all
prefixes except iso, as in isopropyl and isobutyl.
Separate numbers by commas and separate numbers
from letters by hyphens. The name of an alkane is a
single word, with no spaces after hyphens and commas.

17

Alkanes
Introduction:
Carbon atoms in alkanes and other organic compounds
are classified by the number of other carbons directly
bonded to them.

18

Alkanes
Introduction:
Hydrogen atoms are classified as primary (1),
secondary (2), or tertiary (3) depending on the type of
carbon atom to which they are bonded.

19

Degrees of Substitution
Primary (1) Carbon: carbon that is bonded to only one other carbon
Secondary (2) Carbon: carbon that is bonded to two other carbons
Tertiary (3) Carbon: carbon that is bonded to three other carbons
Quarternary (4) Carbon: carbon that is bonded to four other carbons

Primary (1)
Secondary (2)
Tertiary (3)
Quarternary (4)

secondary
alcohol

HO

1 Hydrogens- hydrogens on a primary carbon. -CH3 (methyl group)

2 Hydrogens- hydrogens on a secondary carbon. -CH2- (methylene group)
3 Hydrogens- hydrogens on a tertiary carbon. CH (methine group)
CH3
H3C

CH2

CH

CH3
CH2

C
CH3

CH3

methyl group: 1 hydrogens

methylene group: 2 hydrogens
methine group: 3 hydrogens

20

Alkanes
Introduction:
The maximum number of possible constitutional
isomers increases dramatically as the number of
carbon atoms in the alkane increases. For example,
there are 75 possible isomers for an alkane having 10
carbon atoms, but 366,319 possible isomers for one
having 20 carbons.

The suffix ane identifies a molecule as an alkane.

By increasing the number of carbons in an alkane by a
CH2 group, one obtains a homologous series of
alkanes, as shown in Table 4.1. The CH2 group is
called methylene.
21

Nomenclatura de Alcanos
1.- La base del nombre fundamental, es la cadena continua ms larga
de tomos de carbono.
2.- La numeracin se inicia por el extremo ms cercano a una
ramificacin.
Dos ramificaciones a la misma distancia, se empieza a numerar por
el extremo ms cercano a la ramificacin de menor orden
alfabtico.
Dos ramificaciones del mismo nombre a la misma distancia de cada
uno de los extremos, se busca una tercera ramificacin y se numera
la cadena por el extremo ms cercano a ella.

Hydrocarbons
Formula

Prefix

Suffix

Name

Structure
H

CH4

meth-

-ane

methane

C2H6

eth-

-ane

ethane

C3H8

prop-

-ane

propane

C4H10

but-

-ane

butane

C5H12

pent-

-ane

pentane

C6H14

hex-

-ane

hexane

C7H16

hept-

-ane

heptane

C8H18

oct-

-ane

octane

C9H20

non-

-ane

nonane

C10H22

dec-

-ane

decane

H3C

CH3

Hydrocarbons

Hydrocarbons
Hydrocarbons
Formula

Prefix

Suffix

Name

Structure
H

CH4

meth-

-ane

methane

C2H6

eth-

-ane

ethane

C3H8

prop-

-ane

propane

H3C

CH3

or

C4H10

but-

-ane

butane

H3C

CH3

or

C4H10

but-

-ane

iso-butane

H3C

C
CH3

CH3

or

Hydrocarbons
Hydrocarbons

Formula

C4H10

Prefix

but-

Suffix

-ane

Name

butane

Structure

H3C

CH3

or

C4H10

but-

-ane

iso-butane

H3C

or

CH3

CH3

C5H12

C5H12

C5H12

pent-

pent-

pent-

-ane

-ane

-ane

pentane

H3C

iso-pentane H3C

iso-pentane??? H

CH3 H

CH3 H

CH3 H

CH3

or

or

or

Hydrocarbons
Hydrocarbons

Formula

C4H10

Prefix

but-

Suffix

-ane

Name

Structure

butane

H3C

CH3

or

C4H10

but-

-ane

iso-butane

H3C

or

CH3

CH3

C5H12

C5H12

C5H12

pent-

pent-

pent-

-ane

-ane

-ane

pentane

H3C

iso-pentane H3C

neo-pentane

CH3 H

CH3 H

CH3 H

CH3

or

or

or

Nomenclatura de Alcanos
3.- Cuando en un compuestos hay dos o ms
ramificaciones iguales:

4.- Se escriben las ramificaciones en orden

alfabtico y el nombre del alcano que
corresponda a la cadena principal.

Nomenclatura de Alcanos
Radicales alquilo

Cuando alguno de los alcanos pierde un tomo de hidrgeno se forma un

radical alquilo. Estos radicales aparecen como ramificaciones sustituyendo
tomos de hidrgeno en las cadenas.

IUPAC System of Naming Organic Compounds

1. Find the longest carbon chain
2. Name all the atoms (other than H) not in the longest chain as groups
3. Number groups from the end of the chain closest to the first group
4. List multiple groups in alphabetical order,

H3C

H3C

CH3 H

Longest chain: pentane

CH3
1

CH3 H

CH3 H

Groups: none

pentane

Longest chain: butane

2-methylbutane

Groups: one methyl

not: 3-methylbutane

not:
2

IUPAC Name

3
H

Longest chain: propane

Groups: two methyls

2,2-dimethylpropane

HydrocarbonsOrganic Compounds
IUPAC System of Naming

Formula

C4H10

Prefix

but-

Suffix

-ane

Structure

IUPAC Name

butane

H3C

CH3or

C4H10

but-

-ane

iso-butane

H3C

CH3

CH3

C5H12

C5H12

C5H12

pent-

pent-

pent-

-ane

-ane

-ane

pentane

H3C

2-methyl butane

2,2-dimethylpropane

H3C

CH3 H

CH3 H

CH3 H

CH3

Naming Branches as Groups

Naming Branches as Groups
Group Formula

Prefix

Suffix

Name

Abbreviation

Structure
H

CH3

meth-

-yl

methyl

Me

C2H5

C3H7

eth-

prop-

-yl

-yl

ethyl

propyl

Et

Pr

CH3

or

CH3

or

C3H7

C4H9

iso-prop-

but-

-yl

-yl

iso-propyl

butyl

iPr

Bu

H3C

CH3

or

Naming Branches as Groups

Other Groups We May Encounter

Group Formula

Name

Structure

Group Formula

Name

Structure

C4H9

iso-butyl

fluoro

C4H9

sec-butyl

Cl

chloro

Cl

C4H9

tert-butyl

Br

bromo

Br

C5H11

neo-pentyl

iodo

Rules for Systematic Nomenclature of Alkanes

1. Find the parent chain
a. Identify the longest continuous carbon chain as the
parent chain.
CH3
CH2
CH3

CH

7 carbons = hept-

H
C

CH2

CH2

CH2

CH3
CH3

b. If more than one different chains are of equal length

(number of carbons), choose the one with the greater
number of branch points (substituents) as the parent.
CH3
CH3

CH

CH3
H
C
CH2

CH2

CH2

CH3

2 branch pts.

CH3

CH3

CH

CH
CH2

CH2

CH2

CH3

CH3

1 branch pt.
34

2. Numbering the carbons of the parent chain

a. Number the carbon atoms of the parent chain so that any
branch points have the lowest possible number

CH3

1 CH
3

7 CH3

2 CH2

6 CH2

H
CH
C
3
4
CH2
5

CH2
CH2
6

CH3

CH3

CH
5

CH3
7

branch pts. at carbons 3 and 4

H
C

CH2

CH2

CH2

CH3

4
CH3
1

branch pts. at carbons 4 and 5

b. If there is branching equidistant from both ends of the

parent chain, number so the second branch point has the
lowest number.
1
CH3
CH3

2
CH2
CH
3

H3C
CH2
4

CH2
5

CH
6

CH2
CH
7

CH3

CH3
CH2
8

branch pts. at carbons 3, 6, 7

CH3
9

CH3

8
CH2
CH
7

H3C
CH2
6

CH2
5

CH
4

CH2
CH
3

CH3
CH2
2

branch pts. at carbons 3,4,7

CH3
1

35

3. Substituents
a. Identify and number the substituents and list
them in alphabetical order.
9
CH3
CH3

8
CH2
CH
7

H3C
CH2
6

CH2
5

CH
4

CH2
CH
3

CH3
CH2
2

CH3
1

Parent C-9 = nonane

3- ethyl
4-methyl
4,7-dimethyl
7-methyl

b. If there are two substituents on the same carbon,

assign them the same number.
4. Write out the name
a. Write out the name as a single word:
hyphens (-) separate prefixes
commas (,) separate numbers
b. Substituents are listed in alphabetical order
c. If two or more identical substituents are present use the
prefixes: di- for two
tri- for three
36
tetra- for four

note: these prefixes (di-, tri-, tetra-, etc.) are not used for
alphabetizing purposes
9
CH3

8
CH2

H3C

CH2

CH3

3- ethyl-4,7-dimethylnonane
CH3

CH
7

CH2
6

CH2
5

CH
4

CH
3

CH2
2

CH3
1

5. Complex Substituents (substituents with branching)

a. Named by applying the four previous rules with some
modification
b. Number the complex substituent separately from the parent.
Begin numbering at the point of attachment to the parent
chain
c. Complex substituents are set off by parenthesis.
CH3
1
2
CH3 CH

CH2
3
CH2

4
CH2

5
CH

6
CH

H2 C
1

CH2
2

CH3

7
CH2
CH3
3

8
CH2

9
CH2

10
CH3

2,6-dimethyl-5-(1-methylpropyl)decane
37

Nonsystematic (trivial) Names:

HC
3-carbons:
3

Parent
Chain

CH
H3C

Isop rop yl(1-m ethylethyl)

4-Carbons:

H3C

CH3
CH

H3C

Parent
Chain

H3C

CH2

CH CH2

H3C

CH3

Parent
Chain

C
CH3

Isobutyl(2-methylpropyl)

sec-butyl(1-methylpropyl)

5- Carbons:

Parent
Chain

tert-butyl(1,1-d imethylethyl)

CH3

CH3

H3C
CH CH2 CH2

Parent
Chain

H3C

H3C

CH2

Parent
Chain

CH3
Isopentyl-, isoam yl
(3-methylbu tyl)

neopentyl(2,2-d imethylpropyl)

H3C

CH2

Parent
Chain

CH3
tert-p entyl-, tert-am yl
(1,1-dim ethylpropyl)

Alphabetizing trivial names:

Iso- and neo are part of the alkyl group name and are used for alphabetizing.
sec- and tert- are not included in the alphabetical order.

4-(1-methylethyl)heptane
-or4-Isopropylheptane

2-methyl-6-(2-methylpropyl)decane
-or6-Isobutyl-2-methyldecane

38

Ejemplos de Alcanos

4-ETIL-2-METILHEPTANO

Ejemplos de Alcanos

5-ISOPROPIL-3- METILNONANO

EJEMPLOS DE ALCANOS

3-METIL-5-n-PROPILOCTANO

Alkanes
Physical Properties of Alkanes:

42

Alkanes
Physical Properties of Alkanes:

43