Chapter 1 Notes

CHEM 2353

Fundamentals of Organic Chemistry

Chapter
Chapter

Organic Compounds:
Alkanes

Organic and Biochemistry for Today (4th ed.)

Spencer L. Seager / Michael R. Slabaugh
Mr. Kevin A. Boudreaux

Angelo State University

www.angelo.edu/faculty/kboudrea
1

Organic chemistry nowadays

almost drives me mad. To
me it appears like a primeval
tropical forest full of the
most remarkable things, a
dreadful endless jungle into
which one does not dare
enter, for there seems to
be no way out.
Friedrich Whler
2

Chapter 1 Notes

What Do We Mean By Organic?

In everyday usage, the word organic can be found in
several different contexts:
chemicals extracted from plants and animals were
originally called organic because they came
from living organisms.
organic fertilizers are obtained from living
organisms.
organic foods are foods grown without the use of
pesticides or synthetic fertilizers.
In chemistry, the words organic and organic
chemistry are defined a little more precisely:

Chapter 1 Notes

What is Organic Chemistry?

Organic chemistry is concerned with the study of
the structure and properties of compounds
containing carbon.
All organic compounds contain carbon atoms.
Inorganic compounds contain no carbons. Most
inorganic compounds are ionic compounds.
Some carbon compounds are not considered to be
organic (mostly for historical reasons), such as CO,
CO2, diamond, graphite, and salts of carboncontaining polyatomic ions (e.g., CO32-, CN-).
Inorganic chemistry is the study of the other
elements and non-carbon containing compounds.
5

The Periodic Table

There are 92 naturally occurring elements, and many
artificial ones, in the (in)famous Periodic Table:
VIII A

IA
1
2
3

H II A
Li Be
Na Mg

K
Rb

Cs

Fr

III A IV A V A VI A VII A

He

B C N O F Ne
III B
S Cl Ar
III B IV B V B VI B VII B
I B II B Al Si P
Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Uuq
Ra Ac Rf Db Sg Bh Hs Mt UunUuuUub

Lanthanides

Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu

Actinides

Th Pa U Np Pu AmCm Bk Cf Es Fm Md No Lr

Chapter 1 Notes

The Periodic Table of Organic Chemistry

Organic chemists look at the Periodic Table a little
differently:

H
B
Al

Mg
Cr Mn Fe Co Ni Cu
Pd

N O F
P S Cl
Br
I

Pt

Origins of Organic Chemistry

Organic literally means derived from living
organisms organic chemistry was originally the
study of compounds extracted from living organisms
and their natural products.
It was believed that only living organisms possessed
the vital force necessary to create organic
compounds (vitalism).
This concept started to change in 1828 after
Friedrich Whler showed that it was possible to
make urea, a known organic compound from a
mineral source:
O
NH4+ -OCN
Ammonium
Cyanate

Heat

C
N

H
N

H
Urea

Chapter 1 Notes

Origins of Organic Chemistry

What this and later experiments showed was that
organic molecules even those made by living
organisms can be handled and synthesized just
like minerals and metals
What was special about these molecules was that
they contained the element carbon.

Whats So Great About Carbon?

Carbons atoms can be linked by strong, stable
covalent bonds.
C

neutral carbon, C

carbon cation, C4+

carbide anion, C4-

C
H

H
H

H
10

Chapter 1 Notes

Whats So Great About Carbon?

Carbon atoms can form stable bonds to many other
elements (H, F, Cl, Br, I, O, N, S, P, etc.). Most
organic compounds contain a few hydrogens, and
sometimes oxygen, nitrogen, sulfur, phosphorus, etc.
Carbon atoms can form complex structures, such as
long chains, branched chains, rings, chiral
compounds (having a particular handedness),
complex 3D shapes, etc.
Because of this variety in bonding and complexity,
carbon atoms can form a tremendous variety of
compounds. More than 16,000,000 organic
compounds are known, as opposed to about 600,000
inorganic compounds.
11

Whats So Great About Carbon?

Complex organic compounds can perform a number
of useful biological functions (vitamins,
carbohydrates, lipids, proteins, enzymes, ATP, DNA,
RNA are all organic compounds) which are studied
in biochemistry.
Complex organic compounds are present in the foods
we eat (carbohydrates, proteins, fats, etc.)
Most medicines, whether they come from a chemical
plant or a green plant, are organic compounds.
Most fuels are organic compounds (wood, coal,
natural gas, gasoline, kerosene, diesel fuel, oil, and
other petroleum-based products).
Complex organic compounds are also useful in
technology (paints, plastics, rubber, textiles, etc.).
12

Chapter 1 Notes

Organic vs. Inorganic Compounds

Organic compounds are held together by covalent
bonds, while inorganic compounds are held together
by ionic bonds.
H
methane

H
H

sodium chloride

H
H

Na+

Cl

Na+

Cl

Cl

Na+

Cl

Na+

Na+

Cl

Na+

Cl

Cl

Na+

Cl

Na+
13

Organic vs. Inorganic Compounds

Table 1.1 Properties of typical
inorganic compounds.
Property
Organic
Bonding within
Usually covalent
molecules
Forces between
Generally weak
molecules
liquids, or low
Normal physical state Gases,
melting-point solids

organic and
Inorganic
Often ionic
Quite strong

Flammability

Often flammable

Usually high meltingpoint solids

Usually
nonflammable

Solubility in water

Often low

Often high

Conductivity of
aqueous solutions

Nonconductor

Conductor
14

Chapter 1 Notes

15

Atomic Orbitals on Carbon

A carbon atom does not form ions easily, since it has
four valence electrons (1s22s22p2). It satisfies the
octet rule in compounds by sharing electrons.
2p

2s

s orbital

p orbital
1s
Energy

These are the orbitals that exist on atomic carbon

(not connected to anything).

16

Chapter 1 Notes

Hybrid Orbitals
When carbon atoms form bonds with each other, we
describe the resulting bonds using hybrid orbitals,
which are formed by mixing (hybridizing) the
carbons atomic orbitals. (Linus Pauling, 1950s)
When carbon atoms bond to 4 other atoms, the 2s
and all three 2p orbitals in the valence shell combine
to produce four sp3 orbitals:

2s

4 sp3

3 ( 2p )
atomic orbitals

hybrid orbitals

17

Hybrid Orbitals
2p
sp3
2s
hybridization

1s

1s

Energy

All four sp3 orbitals are at the same energy level,

with one electron in each hybrid orbital.
18

Chapter 1 Notes

The Shape of an sp3 Carbon

In order to get as far away from each other as
possible (thus minimizing electron-electron
repulsions), the sp3 orbitals are arranged in the shape
of a tetrahedron around the central carbon atom,
with bond angles of 109.5.

sp3
109.5
C

sp

sp3

sp3
19

The Shape of an sp3 Carbon

20

Chapter 1 Notes

Bonding in Ethane
Bonds arise from the overlap of orbitals on adjacent
atoms.
End-on-end overlap of sp3 orbitals produces a bond (sigma bond).
All single bonds are -bonds.
Free rotation is possible around -bonds.
Each carbon in the ethane molecule, CH3CH3, is sp3hybridized and tetrahedral in shape. Free rotation is
possible around the CC bond. (See next slide)

21

Bonding in Ethane

22

Chapter 1 Notes

Carbon Chains
Each carbon atom can form four bonds, either to
other carbon atoms, or to different atoms (such as H,
O, N, S, P, etc.)
Three more sites
to make bonds

C C

C
C

C
C

C
C

etc.

23

Multiple Bonds
Carbon atoms form four bonds to other things, but
sometimes those bonds are multiple bonds (double
or triple bonds):

single bond
results from the sharing
of two electrons

double bond
results from the sharing
of four electrons

triple bond
results from the sharing
of six electrons
24

Chapter 1 Notes

Isomers
Isomers compounds having identical molecular
formulas, but different arrangements of atoms.
Structural Isomers the atoms in each molecule
are connected in a different order.

C2H6O

H
O

Ethyl Alcohol

Dimethyl Ether

Colorless liquid

Colorless gas

mp -117C

mp -139C

bp 78.5C

bp -25C

density 0.789 g/mL (20C)

density 0.00195 g/mL (20C)

Intoxicant

Refrigerant

25

Examples: Isomers
Draw all possible structures having the formulas
C4H10, C5H12, and C6H14.

C7H16
C8H18
C9H20
C10H22
C20H42
C30H62
C40H82

9 isomers
13 isomers
35 isomers
75 isomers
366,319 isomers
4,111,846,763 isomers!
62,481,801,147,341 isomers!
26

Chapter 1 Notes

Examples: Isomers
Which of the following
molecules is a structural
isomer of acetone?

O
CH3

CH3

Acetone

O
H2C

CH

OH
H

H2C

CH

O
H3C

CH2

CH2

O
OH

H3C

CH2

27

Functional Groups
Organic molecules are often organized by structures
called functional groups, which are characteristic
arrangement of atoms which define many of the
physical and chemical properties of a class of
organic compounds.
The simplest of the functional groups are the
hydrocarbons, which include the alkanes,
alkenes, alkynes, and aromatic hydrocarbons.
Many functional groups contain oxygen atoms,
such as alcohols, ethers, aldehydes, ketones,
carboxylic acids, and esters.
Some other functional groups contain nitrogen
atoms, such as the amines and amides.
Molecules with the same functional group tend to
share similar chemical and physical properties.

28

Chapter 1 Notes

Table 1.2 Classes and functional groups of organic compounds

Class

Functional Group

Alkane

Example of expanded
structural formula

None

H
Alkene

C
C

CH2

ethene (ethylene)

HC

CH

ethyne (acetylene)

benzene

H
Ether

Alcohol

H2C

ethane

Aromatic

CH3CH3

IUPAC / Common name

H
Alkyne

Example of condensed
structural formula

CH3CH2OH

CH3OCH3

ethyl alcohol

H
O

methoxymethane
(dimethyl ether)

29

Table 1.2 Classes and functional groups of organic compounds

Class

Functional Group

Example of expanded
structural formula

O
Aldehyde

Example of condensed
structural formula

IUPAC / Common name

O
CH3CH

ethanal (acetaldehyde)

H
O
Ketone

H
O
Carboxylic acid

O
H

CH3CCH3

CH3COH

2-propanone (acetone)

O
O

ethanoic acid (acetic acid)

H
O
Ester

CH3COCH3

methyl ethanoate
(methyl acetate)

H
Amine

CH3NH2

methylamine

H
O
Amide

O
N
H

CH3CNH2

ethanamide (acetamide)

30

Chapter 1 Notes

31

A Moderately Complex Organic Molecule

H
H

H
C

H
H
H
H
H
H

H H C H
H
C
C
C
C

C
C
C

C
C

HO
H
H

H
C

C
C

H
H

H
C

C
H

H
H

H C

C
H

H
H
32

Chapter 1 Notes

Expanded Structural Formulas

In expanded structural formulas (Lewis formulas,
Lewis structures), all atoms and bonds are shown:

H
O

H
33

Condensed Structural Formulas

In condensed structural formulas, only specific
bonds are shown; this is useful in reducing the
number of CH bonds that must be drawn.
H3C

CH3

CH3

CH3

CH2

CH

CH3

CH2

CH3CH3

CH3

CH2

OH

CH3CH2OH

CH3

CH2

CH3

CH3CH2OCH2CH3

34

Chapter 1 Notes

Line Drawings
In line drawings (line-angle formulas, skeletal
structures, stick figures), bonds are represented by
lines; everywhere two lines meet or a line begins or
ends is a C atom. Hs on Cs are not shown (except
for emphasis); Hs on other atoms must be shown.

OH

35

Drawing Organic Molecules

Expanded structural formula
(Lewis structure)

Condensed structural formulas

CH3 CH2 CH2 CH3

CH3CH2CH2CH3
CH3(CH2)2CH3
= CH3

Line drawing

= CH
= C
= CH2

36

Chapter 1 Notes

Drawing Organic Molecules

H

Cholesterol

H
C

H
H
H
H
H
H

H H C H
H
C
C
C
C

C
C
C

HO
H

H
C

C
C

H
H

H
C

C
H

H
H

C
H

H C

Expanded Structural Formula

37

Drawing Organic Molecules

CH3
H2
C
H2
C
H2C

H2C
C
CH3
CH
CH
C
CH

C
H2

CH
CH2
C
H2

CH2

CH
HO

CH3 CHCH2CH2CH2CH(CH3)2

C
H

Condensed Structure
38

Chapter 1 Notes

Drawing Organic Molecules

HO

Line Drawing
39

Examples: Drawing Organic Molecules

Draw acceptable condensed structures and line
drawings associated with the following expanded
structural formulas.
H

H
H

H3C
H

H
H

H
H
H

H
H

CH3
H

C
C

C
C
H

H
H
H

Draw an acceptable expanded

structure and line drawing for
the molecule CH3CH2CH2OH.

40

Chapter 1 Notes

Examples: Drawing Organic Molecules

Draw acceptable expanded structures, condensed
structures, and line drawings for the following
molecules:
isopropyl alcohol, CH3CH(OH)CH3
acetic acid, CH3COOH
acetaldehyde, CH3CHO
acetone, CH3COCH3

41

42

Chapter 1 Notes

43

Hydrocarbons
Hydrocarbons compounds that contain only
carbon and hydrogen.
Saturated Hydrocarbons contain only carboncarbon single bonds. H H
H

Alkanes

Unsaturated Hydrocarbons contain carboncarbon double or triple bonds.

H
H

C
C

H
H

H
C

H
C

Alkynes

C
C

Alkenes

H
Aromatics

44

Chapter 1 Notes

Alkanes
Alkanes are saturated hydrocarbons each carbon
holds the maximum number of hydrogen atoms).
Alkanes contain only carbon-carbon single bonds.
General formula: CnH2n+2 (no rings).
Most chemical reactions require a functional group
handle to proceed. Since alkanes dont really have
functional groups, they arent very useful in many
biologically important processes.
Since alkanes undergo combustion easily, they
are a good source of energy (e.g., gasoline).
Alkanes also provide the raw materials for the
production of many other more complex
substances (plastics, etc.).
45

Some Common Alkanes

Methane, CH4
major component of natural gas (~85%), which is
produced by bacterial decomposition of
organisms in the absence of oxygen (marsh gas,
cow flatulence).
burns cleanly, so is useful for cooking.
odorless ethanethiol is added to make natural
gas leaks detectable.
Ethane, CH3CH3 (C2H6) a minor component of
natural gas (~10%).
Propane, CH3CH2CH3 (C3H8) used as an
industrial fuel, and in home heating and cooking.
46

Chapter 1 Notes

Some Common Alkanes

Butane, CH3CH2CH2CH3 (C4H10)
cigarette lighters
Butane is an unbranched (normal) alkane.
There is also a branched alkane with the formula
C4H10, having a three-carbon chain with a onecarbon group connected to the middle.
We must give the other isomer a different name:
CH3CH(CH3)CH3 [or CH3CH(CH3)2] is named
isobutane (or 2-methylpropane).
Butane and isobutane are structural isomers of
each other.
CH3
CH3CH2CH2CH3

CH3CHCH3

Butane

Isobutane

47

Conformations of Alkanes
Conformation the different arrangements of
atoms in space achieved by rotation about single
bonds.
Structures which are related to each other by rotation
around a single bond are the same molecule.
CH3CH2CH2CH3
CH3

CH3
H

H CH

H
CH3

H
CH3

CH3

HH

H
H

CH3

CH3

H
CH3

CH3
CH3

HH

CH3

48

Chapter 1 Notes

Examples: Conformations and Isomers

Which of the following groups represent structural
isomers, and which are simply the same compound?
CH2
CH3

CH2

CH2

CH3

CH3

CH2

CH2

CH3

CH3

CH2

CH3

CH2

CH3
CH3

CH3

CH3

CH2

CH2

CH2

CH2

CH3

CH2
CH3

CH3

CH3

CH2

CH2

CH3

CH

CH3

CH3

CH2

CH2

CH2

CH2
49

Examples: Conformations and Isomers

Which of the following groups represent structural
isomers, and which are simply the same compound?
CH3
CH3

CH3
CH3

CH3

CH

CH

CH

CH3

CH3

CH3

CH

CH2

CH3

CH2
CH3

CH3

CH3

CH3

CH3
CH3

CH3

CH3

CH2

CH

CH3

CH3

CH2

CH3

CH3

CH3

CH3
CH3

CH

CH

CH3
CH2

CH2 CH3

CH3

CH2 CH

CH2

CH3
50

Chapter 1 Notes

Alkane Nomenclature
Straight-chain alkanes are named by combining a
prefix which indicates the number of carbon atoms
in the chain, and a suffix indicating the functional
group of the molecule.
No. of Cs
1
2
3
4
5
6
7
8
9
10

Prefix
methethpropbutpenthexheptoctnondec-

Functional
Group
Alkane
Alkene
Alkyne

Suffix
-ane
-ene
-yne

51

Alkane Nomenclature
When alkanes are branched, things get more
complex. Remember there are two isomers of C4H10:
CH3
CH3CH2CH2CH3

CH3CHCH3

Butane

Isobutane

There are three isomers of C5H12:

CH3
CH3CH2CH2CH2CH3

CH3CHCH2CH3

Pentane

Isopentane

CH3
CH3

CH3

CH3
Neopentane

There are 75 isomers of C10H22!

We need a way to name molecules that doesnt
require memorizing a huge number of prefixes.
52

Chapter 1 Notes

IUPAC System of Chemical Nomenclature

The system of nomenclature used to name organic
compounds was developed by the International
Union of Pure and Applied Chemistry (IUPAC).
A root identifies the longest continuous chain of
carbon atoms.
A suffix identifies the main functional group in
the molecule.
A set of prefixes identifies the numbers and
positions of the substituents (groups which are
attached to the longest chain). (Alkyl groups are
substituents which contain a carbon chain.)
Prefix

Root

Ending

number and
identity of
attached groups

longest carbon
chain

functional
class
53

IUPAC Nomenclature of Alkanes

Step 1. Identify and name the longest continuous
chain of C atoms (#C + -ane for alkanes).
CH3

CH3
CH3 CH CH2 CH2

CH3

CH3 CH

CH3
CH2

CH3

CH3

CH3

CH2

CH3 CH CH2 CH

CH3
CH3

CH3

CH3 CH

CH3

CH3 CH2 CH CH2 CH3

CH2 CH3

CH3 CH2 CH CH2 CH CH2 CH3

54

Chapter 1 Notes

IUPAC Nomenclature of Alkanes

Step 2. Number the atoms in the longest chain.
Number consecutively from the end that will give
the lower number to any C to which a group is
attached.
If two or more alkyl groups are attached to the
longest chain, use the numbering path that gives
the lowest number for the first point of difference.
If two different alkyl groups are attached at the
same distance from either end of the chain, the
one that comes first in alphabetical order has the
highest priority.
If there is more than one way to get a certain
number of atoms in the longest chain, go with the
way that gives more substituents.
55

IUPAC Nomenclature of Alkanes

Step 3. Name the alkyl groups (#C + -yl) and
other substituents connected to the longest chain.
In front of each alkyl group name, put the number of
the carbon the group is attached to, separated from
the name by a dash (e.g., 2-methyl).
Step 4. If there is more than one of a particular
substituent, combine them into a single word using
the appropriate counting prefix (di-, tri-, tetra-,
etc.). Include all of the carbon numbers which the
groups are attached to, separated by commas (e.g.,
2,2,3-trimethyl).
No. of Groups
1
2
3
4
5

Prefix

ditritetrapenta-

No. of Groups
6
7
8
9
10

Prefix
hexaheptaoctanonadeca-

56

Chapter 1 Notes

IUPAC Nomenclature of Alkanes

Step 5. Arrange the alkyl groups in front of the
parent name in alphabetical order (ignoring
counting prefixes). Always separate numbers by
commas, and numbers from words by dashes.
CH3

CH3
CH3 CH CH2 CH2

CH3 CH

CH3

CH3
CH2

CH3

CH3

CH2

CH3

CH3 CH CH2 CH

CH3 CH

CH3
CH3

CH3

CH3 CH2 CH CH2 CH3

CH3

CH2 CH3

CH3 CH2 CH CH2 CH CH2 CH3

57

Examples: Alkane Nomenclature

Draw structural formulas and give the correct names
for all of the possible structural isomers of butane.
Draw structural formulas and give the correct names
for all of the possible structural isomers of pentane.
Draw structural formulas and give the correct names
for all of the possible structural isomers of hexane.
Provide acceptable IUPAC names for the following
molecules:
CH3

CH2

CH2

CH
CH2

CH3

CH3

CH

CH3

CH3

CH

CH3

CH3
58

Chapter 1 Notes

Common Substituents
Common Alkyl Groups
methyl
ethyl
propyl

CH2CH2CH2CH3

butyl

CH3
CH2CH3

CH3

sec-butyl

CH2CH2CH3

CH CH2 CH3
CH3

CH3

isopropyl

CH2 CH CH3

isobutyl

CH CH3

CH3

tert-butyl

Common Nonalkyl Groups

fluoro

iodo

chloro

Cl

nitro

NO2

bromo

Br

amino

NH2

CH3

CH3

59

Examples: Alkane Nomenclature

Provide acceptable IUPAC names for the following
molecules:
CH2
CH3 CH2

CH3

C CH3
CH2 CH2

CH3 CH2
CH3

CH3

Br

C CH2

CH

CH3

CH3
Cl

CH3 CH2

CH2

CH

CH2

CH2

CH3

CH3 CH CH2 CH3

CH3 CH CH3
CH3 CH CH2 CH CH2 CH2 CH3
F

CH3

CH

CH CH3

CH2

CH3

CH3
CH3CCH3
CH3CH2CH2CHCHCH2CH2CH3
CH3CHCH3
60

Chapter 1 Notes

Examples: Alkane Nomenclature

Draw condensed structural formulas or line drawings
for each of the following compounds:
3-ethylpentane
2,2-dimethylbutane
3-ethyl-2-methylhexane
4-isopropyloctane
6-sec-butyl-7-ethyl-2,2,5,8-tetramethylnonane
The following names have been assigned incorrectly.
Draw the structure corresponding to the name, and
assign the correct IUPAC name.
3-sec-butylpentane
2-ethyl-2,6-dimethylhexane

61

Cycloalkanes
Alkanes may also possess cyclic structures in
addition to the straight- and branched-chain acyclic
molecules we have already seen.
General formula: CnH2n (for one ring)
H

H
~ 60

C
CH3CH2CH3
Acyclic
Propane

C
H

Note that these

molecules are
not structural
isomers of
each other!

Cyclic
Cyclopropane

STOP
cyclobutane

cyclopentane

cyclohexane

cyclooctane

62

Chapter 1 Notes

Cycloalkane Nomenclature
When naming cycloalkanes, the ring is taken to be
the longest chain; the prefix cyclo- is added to the
normal root + -suffix.
When mono-substituted cycloalkanes are named, it
is not necessary to specify the position number,
since all positions in the ring are equivalent.
When more than one substituent is located on a ring,
the numbering begins at the carbon to which the
group is attached which comes first in alphabetical
order, and then proceeds in a direction which gives
the lowest possible number to the next attached
group.

63

Examples: Cycloalkane Nomenclature

Provide acceptable IUPAC names for the following
molecules:
CH3

CH3

Cl

CH3
CH3

CH3

CH3
CH3

CH3

Cl
Cl

CH2CH3

Cl

CH3
CH2 CH CH3

64

Chapter 1 Notes

The Shape of Cycloalkanes

Cyclopropane has bond angles of 60, which is bent
far away from the normal 109.5 bond angles of
straight-chain alkanes. It is a flat molecule.
HH
~ 60
H
H

Cyclobutane has bond angles of about 90; it is also

less stable than a normal alkane. It is mostly flat,
but there is some slight puckering of the ring.
H

H
H
~ 90

H
H

65

The Shape of Cycloalkanes

Cyclopentane has bond angles of about 108; it
forms a mostly flat but slightly puckered ring.
Cyclopentane rings are very common in nature.
HH
H
H

H
H
~ 108
H
H

H H

If cyclohexane were flat, the bond angles would be

about 120; but this molecule can adopt a chair or
boat conformation in which the bond angles are
109.5. Cyclohexane rings are extremely common.

"chair"
conformation

"boat"
conformation

66

Chapter 1 Notes

Stereoisomers of Cycloalkanes
The molecules below are different molecules
because there is no free rotation around carboncarbon bonds in cycloalkanes.
CH3
CH3

CH3

CH3

cis-1,2-dimethylcyclopentane

trans-1,2-dimethylcyclopentane

These molecules are stereoisomers compounds

with the same molecular and structural formula but
different spatial arrangements of atoms.
Stereoisomers in which the spatial arrangement is
maintain by rings (or double bonds) are called
geometric isomers or cis-trans isomers.
67

Examples: Stereoisomers
State whether each possible pairing of the molecules
below are structural isomers, geometric isomers, or
the same molecule.
CH3

CH3

CH3

CH3
CH3

CH3
CH3
CH3

CH3

CH3
CH3

CH3
CH3

CH3

CH3

CH3

Name the following molecules:

Br

Br

Br

Br

68

Chapter 1 Notes

69

Physical Properties of Alkanes

Since alkanes are composed of relatively nonpolar
CC bonds and CH bonds, alkanes are
nonpolar molecules.
Because they have only weak attractions for each
other, they tend to have lower melting points and
boiling points than other organic compounds of
comparable molecular weights.
The straight chain alkanes make up a homologous
series in which each members differs from a
previous member by having one additional CH2
group. In a homologous series, the physical
properties are closely related and vary in a
systematic way.
70

Chapter 1 Notes

71

Physical Properties of Alkanes

The general rule when judging solubility is like
dissolves like polar substances mixes with polar
substances, nonpolar with nonpolar, but not polar
with nonpolar.
Alkanes (nonpolar) are insoluble in water (polar),
and since they are less dense than water, they float
(e.g., oil slicks).
Alkanes and other substances that do not dissolve in
water are often referred to as being hydrophobic
(water fearing).
Liquid alkanes of high molecular weight serve as
emollients (skin softeners) to replace oils washed
away by bathing or swimming.
Vaseline is a semisolid mixture of alkanes.
72

Chapter 1 Notes

Alkane Reactions
Alkanes are the least reactive of all organic
compounds. They do not usually react with strong
acids or bases, or with most oxidizing or reducing
agents.
They do, however, burn very easily in combustion
reactions, releasing a great deal of energy:
CH4(g) + 2O2(g) CO2(g) + 2H2O(g) + 212.9 kcal
C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g) + 488.8 kcal
2C8H18(g) + 25O2(g) 16CO2(g) + 18H2O(g) +
2448 kcal
73

Alkane Reactions
In the absence of enough oxygen for complete
conversion to carbon dioxide, some common waste
products are generated in the incomplete burning of
alkanes:
CH4(g) + 2O2(g) CO2(g) + 2H2O(g)
CH4(g) + 3/2 O2(g) CO(g) + 2H2O(g)
CH4(g) + O2(g) C(s) + 2H2O(g)
CO, carbon monoxide, is poisonous, colorless,
and odorless. In the exhaust train of most cars, a
catalytic converter converts CO to CO2.
Solid elemental carbon produces engine deposits;
but this reaction is done to produce lampblack,
which is used in some ink pigments.
74

Chapter 1 Notes

Alkyl Halides
Alkyl halides, or haloalkanes, are alkanes in which
one or more hydrogen atoms are replaced by
halogen atoms (F, Cl, Br, or I).
Most alkyl halides are not very water-soluble. Alkyl
fluorides and chlorides have densities that are higher
than those of alkanes, but still less than that of water.
Alkyl bromides and iodides are generally more
dense than water. Compounds containing more than
one halogen are often more dense than water.
Alkyl halides are named as alkanes with halosubstituents (fluoro-, bromo-, chloro-, and iodo-).
A number of simple alkyl halides are better known
by their common names; for instance, CHCl3,
trichloromethane, is almost always referred to as
chloroform.

75

Some Common Alkyl Halides

Cl
H

Cl
H

Cl
Cl

Cl

Cl

Cl

Cl

Cl

Dichloromethane
(methylene chloride)
A colorless , mildly toxic
liquid (bp 41C) more dense
than water. It is used as a
paint remover and degreaser.
It is also used to decaffeinate
coffee beans; since it has
such a low boiling point, the
residual solvent can be
removed from the beans at
fairly low temperatures.

Trichloromethane (chloroform)
A colorless liquid (bp 60C); a
very commonly used organic
solvent. Chloroform vapor is a
anesthetic: James Young
Simpson was the first to use
chloroform as an anesthetic
during childbirth in 1846
(presumably, not on himself!),
and it was widely used in surgery
in the 19th and early 20th
centuries. However, since
chloroform is carcinogenic, and
toxic to the liver, it is not widely
used for this purpose anymore.

Tetrachloromethane
(carbon tetrachloride)
Formerly a common organic
solvent, and was widely used
for dry cleaning and spot
removal; it has been shown to
be toxic and carcinogenic,
and contributes to ozone
depletion, so it has been
replaced by other solvents.

76

Chapter 1 Notes

Some Common Alkyl Halides

Cl

Cl

Cl

F
H

Br

Cl

1,1,1-Trichloroethane
Formerly a very commonly used
organic solvent; heavily used in
dry cleaning, but it has been
replaced by other solvents (such
as tetrachloroethylene).

Bromochlorodifluoromethane (Halon 1211)

An example of a halon, a haloalkane that has
bromine atoms in addition to chlorine and fluorine
atoms. Halons are very stable, and are useful in
fire extinguishers, since they do not damage
electronic equipment. Their use has largely been
phased out under the Montreal Protocols, but they
are still used in fire suppression systems aboard
some aircraft, since no completely satisfactory and
safe alternatives have been discovered.

77

Chlorofluorocarbons (CFCs)
Cl
F

C
Cl

Cl
F

Dichlorodifluoromethane (Freon-12)
Chlorodifluoromethane (Freon-22)
An example of the chlorofluorocarbons (CFCs, or
An example of a hydrochlorofluorocarbon
freons), developed in the 1920s; they are relatively
(HCFC), developed as alternatives to the
nontoxic, very unreactive, and boil at low temperatures, and CFCs. The HCFCs are not fully halogenated,
were thus ideal for use as refrigerants; they were also
and are less stable than the CFCs, and degrade
widely used as aerosol propellants and as foaming agents.
before they reach the upper atmosphere.
Unfortunately, they persist in the environment for a long
F
H
time (up to a century), and make their way into the upper
atmosphere, where they are split by high energy light from
F
C
C
F
the Sun, releasing chlorine atoms. These Cl atoms destroy
ozone in the stratospheric ozone layer that shields us from
much of the Sun's UV radiation. (F. Sherwood Rowland,
F
H
Mario J. Molina, Paul Crutzen, Nobel Prize in Chemistry,
1,1,1,2-Tetrafluoroethane
(Freon-134a)
1995) In 1987, a treaty called the Montreal Protocol on
A hydrofluorocarbon (HFC), another
Substances that Deplete the Ozone Layer was signed, which
group of CFC-alternatives that are not
cut back on the production and use of CFCs; in 1990, in
damaging to the ozone layer. Freon-134a
response to the alarming increase in the size of the "ozone
is now widely used in the air conditioning
hole" over the South Pole, the agreement was extended to
systems of automobiles in place of
become a ban on the use of CFCs starting in 2000.
78
Freon-12.

Chapter 1 Notes

Petroleum
Petroleum is a mixture of hydrocarbons formed
over millions of years, primarily from the decay of
microscopic ocean-dwelling plants and animals.
The resulting crude oil collects in underground
pockets in sedimentary rock.
Petroleum is separated into different fractions by
fractional distillation.
Most petroleum products are burned as fuel, but
about 2% is used to synthesize other organic
compounds. (Thats still a lot!)
Over half of all synthetic industrial organics,
including dyes, drugs, plastics, fibers, detergents,
insecticides, etc., are made from petroleum sources
79

Table 1.9 Petroleum Fractions

Fraction

MolecularBoiling Range size range

Typical uses

Gas

-164-30C

C1-C4

Heating, cooking

Gasoline

30-200C

C5-C12

Motor fuel

Kerosene

175-275C

C12-C16

Fuel for stoves; diesel

and jet engines

Heating oil

Up to 375C

C15-C18

Furnace oil

Lubricating
oils

350C-up

C16-C20

Lubrication, mineral oil

Greases

Semisolid

C18-up

Lubrication, petroleum
jelly

Paraffin
(wax)

Melts 52-57C C20-up

in
Pitch and tar Residue
boiler

High

Candles, toiletries
Roofing, asphalt paving

80

Chapter 1 Notes

Carbon, in fact, is a singular element: it is the

only element that can bind itself in long stable
chains without a great expense of energy, and
for life on earth (the only one we know so far)
precisely long chains are required. Therefore
carbon is the key element of living substance:
but its promotion, its entry into the living
world, is not easy and must follow an obligatory,
intricate path . . . If the elaboration of carbon
were not a common daily occurrence, on the
scale of billions of tons a week, wherever the
green of a leaf appears, it would by full right
deserve to be called a miracle.
Primo Levi, Carbon in

The Periodic Table (1975)

81

The End
82

Chapter 1 Notes

83

Complex Organic Names

O
CH3

N
O

CH3

3,7-Dihydro-1,3,7-trimethyl-1Hpurine-2,6-dione

CH3

OH

3,7-Dimethyl-9-(2,6,6-trimethyl-1cyclohex-1-enyl)-2,4,6,8-nonatetraen-1-ol

Vitamin A

84

Chapter 1 Notes

CH3

2-Diethylamino-N-(2,6dimethylphenyl)acetamide

O
N

N
H

Lidocaine

CH3
O

(+)-cis--4-(2,5,6,6-tetramethyl-2cyclohexen-1-yl)-3-butene-2-one

H3C

CH3

-Irone

H
CH3

CH3
N

[1R-(exo,exo)]-3-benzyloxy-8methyl-8-azabicyclo[3.2.1]octane2-carboxylic acid ethyl ester

CO2CH2CH3
H

Cocaine

O
H

85

OH

HN

OH
O

HO
O

H
O
O

Taxol
5-, 20-epoxy-1,2--4,7-, 10-, 13--hexahydroxytax11-en-9-one 4,10-diacetate 2-benzoate 13-ester with
(2R,3S)-N-benzoyl-3-phenylisoserine

86

Chapter 1 Notes

OH

O
O

HO

OH
OH
HN
HN

NH2

5-(acetylamino)-4[(aminoiminomethyl)-amino]-2,6anhydro-3,4,5-trideoxy-D-glyceroD-galacto-non-2-enoic acid;
Zanamivir; Relenza

O
O

NH

OH

HO

N
OH

4-[1-hydroxy-4-[4(hydroxydiphenylmethyl)1-piperidinyl]-butyl]-,dimethylbenzeneacetic
acid hydrochloride;
fexofenadine HCl;
Allegra
87

6-(1-Piperidinyl)-2,4-pyrimidinediamine3-oxide; Minoxidil; Loniten;

O
Rogaine; Regain

O
H2N

HN

NH2

O
OH

O
OH

1-[[3-(6,7-dihydro-1-methyl-7-oxo-3propyl-1H-pyrazolo[4,3-d]pyrimidin-5yl)-4-ethoxyphenyl]sulfonyl]-4methylpiperazine citrate; sildenafil HO

citrate; Viagra

OH

O
88