HBT 2103; BASIC

ORGANIC CHEMISTRY
Lecture 3

Dr Mariah Onditi 1
 Leaning Objectives

After completing this section, you should be able to

1. Have an understanding of reactivity of alkanes

2. Provide the correct IUPAC name for alkene both condensed or shorthand structure.
3. Give the IUPAC equivalent of the following trivial names: ethylene, propylene,
isobutylene and isoprene. draw the structure of a vinyl (ethenyl) and allyl (2-propenyl)
group, and use these names in alkene nomenclature

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Recall; Physical properties of alkanes

• Since alkanes are composed of relatively nonpolar C—C bonds and C—H 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 CH 2 group. In a
homologous series, the physical properties are closely related and vary in a
systematic way.

• “like dissolves like” — polar substances mixes with polar substances, nonpolar
with nonpolar, but not polar with nonpolar

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 Physical properties of alkanes

• 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.

The bright red color of tomatoes is due to an alkene (lycopene)

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Alkane Reactions In the absence of enough oxygen for complete
• Alkanes are the least reactive of all organic conversion to carbon dioxide, some common waste
compounds. They do not usually react with products are generated in the incomplete burning of
strong acids or bases, or with most oxidizing or alkanes:
reducing agents.
• They do, however, burn very easily in
combustion reactions, releasing a great deal of
energy

– CO, carbon monoxide, is poisonous, colorless, and

odorless.
v In the exhaust train of most cars, a catalytic
converter converts CO to CO2.
v Solid elemental carbon produces engine deposits;
but this reaction is done to produce lampblack,
which is used in some ink pigments.
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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.” we will learn more on alkyl halides in lecture 4.

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Significance of saturated and unsaturated
hydrocarbons.
• Our modern society is based to a large degree on the chemicals.
Most are made from petroleum., we noted that alkanes—
saturated hydrocarbons—have relatively few important
chemical properties other than that they undergo combustion
and react with halogens. Unsaturated hydrocarbons—
hydrocarbons with double or triple bonds—on the other hand,
are quite reactive

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v Alkenes serve as building blocks for many familiar
v Upper left, a stainless steel and ultra high
plastics—polyethylene, vinyl plastics, acrylics—and
molecular weight polyethylene hip
other important synthetic materials (e.g., alcohols,
replacement figure 2.1 a. The polyethylene
antifreeze, and detergents)
repeating unit is shown in the lower left.
v Figure 2.1 b , shatterproof acrylic plexiglas
used to build a large indoor aquarium.
The methylacrylate repeating unit is
shown 2.1 b in the lower middle.
v Figure 2.1 c , common PCV piping used as
material being used for sewage and drains.
v The polyvinylchloride repeating unit is
shown in the lower left

a b c
Figure2.1 Common polymers made using alkene building
blocks Dr Mariah Onditi 8
Alkene and Alkyne Overview
By definition, alkenes are hydrocarbons with one or more carbon–carbon double
bonds (R2C=CR2), while alkynes are hydrocarbons with one or more carbon-carbon
triple bonds (R–C≡C–R). Collectively, they are called unsaturated hydrocarbons,
which are defined as hydrocarbons having one or more multiple (double or triple)
bonds between carbon atoms. As a result of the double or triple bond nature, alkenes
and alkynes have fewer hydrogen atoms than comparable alkanes with the same
number of carbon atoms. Mathematically, this can be indicated by the following
general formulas:

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q In an alkene, the double bond is shared by the two
Physical Properties of Some Selected
carbon atoms and does not involve the hydrogen Alkenes
atoms, although the condensed formula does not
make this point obvious, ie the condensed formula
for ethene is CH2CH2.
q The double or triple bond nature of a molecule is
even more difficult to discern from the molecular
formulas.
q Note that the molecular formula for ethene is
v The US chemical industry produces about 25 billion
C2H4, whereas that for ethyne is C2H2. It is useful
kilograms of ethylene annually, more than any other
to draw out line or partially-condensed structures,
synthetic organic chemical. More than half of this
as shown below:
ethylene goes into the manufacture of polyethylene, one
of the most familiar plastics.
v Propylene is also an important industrial chemical. It is
converted to plastics, isopropyl alcohol, and a variety of
other
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 2. Without consulting tables, arrange the following
alkenes in order of increasing boiling point:

Figure 2.2. Ethene and Propene The ball-and- 3. Without referring to a table or other reference, predict
spring models of ethene/ethylene (a) and
which member of each pair has the higher boiling point.
propene/propylene (b) show their respective shapes,
especially bond angles. i. 1-pentene or 1- butene

Review Exercises
1. Briefly describe the physical properties of
alkenes. How do these properties compare to
those of the alkanes? ii. 3-heptene or 3- nonene

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 Naming of Alkenes
2. Start numbering from the end of the parent chain
Alkenes contain carbon-carbon double bonds and are
which gives the lowest possible number to the
unsaturated hydrocarbons with the molecular formula is
double bond. If the double bond is equidistant from
CnH 2 n; this is also the same m o l ec ul a r f o rm ul a a s
both ends of the parent chain, number from the end
cycloalkanes. The parent chain of an alkene is the longest
which gives the substituents the lowest possible
chain containing both carbon atoms of the double bond and
number. The double bond in cycloalkenes do not
are named by dropping the -ane ending of the parent and
need to number because they are in the one position.
adding -ene. Also, the position of double bond in the
parent chain of the alkene is indicated with a number.
The Basic Rules for Naming Alkenes

For straight chain alkenes, it is the same basic rules as

nomenclature of alkanes apply except the -ane suffix is
changed to -ene.

1) Find the longest carbon chain that contains both carbons

of the double bond.
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3. Place the location number of the double bond
directly before the parent name. The location number
indicates the position of the first carbon of the double
bond. Add substituents and their position to the alkene
as prefixes. Substituents are written in alphabetical
order.

The presence of multiple double bonds is indicated by

using the appropriate suffix such as -diene, -triene,
etc. Each of the multiple bonds receives a location
number. Overall, the name of an alkene should look
like

(Location number of substituent)-(Name of substituent)-

(Location number of double bond)-(Name of parent chain)
+ ene

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 Naming Cycloalkenes
Newer IUPAC Nomenclature Because there are no chain ends in cycloalkenes, the

In 1993 IUPAC updated their naming double bond is assumed to numbered C1 and C2

recommendation to place the location number of and its location number is not required in the name.

the double bond before the -ene suffix of alkene The direction of the numbering is determined by

names. The provides names such as hex-2-ene which will give the substituent closest to the double

rather than 2-hexene. The newer system is slowly bond the lowest number. If multiple double bonds

being accepted so it may occasionally be are present, it may be necessary to include their

encountered. location numbers in the name. One of the double

bonds will be number C1 and C2 and the
numbering direction is determined by which gives
the remaining double bonds the lowest possible
number

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 Methylenecylopentane is an example of an
exocyclic double bond.

1-methylcyclobutene. The methyl group

places the double bond. It is correct to also
name this compound as 1-methylcyclobut-
1- ene

Cyclopentene is an example of an endocyclic double bond.

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1ethenylcyclohexene, the methyl group
places the double bond. It is correct to also
name this compound as ethenylcyclohex-1-
ene. A common name would be 1-
vinylcyclohexene. In addition, the common name some small
alkene compounds are still accepted by
IUPAC. It is important to be able to identify
them.

Common Names of Alkene Fragments

Some alkene containing fragments have common

names which should be recogn i z ed . T h es e
common names can be used to simplify naming
much the alkyl fragments. Some of these
fragments are the methylene group (H 2 C=), the
vinyl group (H 2 C=CH-), and the allyl group
(H2C=CH-CH2-). Dr Mariah Onditi 16
 Alkynes
Note Acetylene is used in oxyacetylene torches for cutting
The simplest alkyne—a hydrocarbon with carbon-to-
and welding metals. The flame from such a torch can be
carbon triple bond—has the molecular formula
very hot. Most acetylene, however, is converted to
C2H2 and is known by its common name—acetylene
chemical intermediates that are used to make vinyl and
(Fig 3.3). Its structure is H–C≡C–H.
acrylic plastics, fibers, resins, and a variety of other
products.
Alkynes are similar to alkenes in both physical and
chemical properties. For example, alkynes undergo many
of the typical addition reactions of alkenes. The
Figure 3.4 Ball-and-Spring Model of Acetylene.
International Union of Pure and Applied Chemistry
Acetylene (ethyne) is the simplest member of the alkyne
(IUPAC) names for alkynes parallel those of alkenes,
family.
except that the family ending is -yne rather than -ene. The
IUPAC name for acetylene is ethyne. The names of other
alkynes are illustrated in the following exercises.
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Review Exercises
1. Briefly identify the important differences between an alkene and an alkyne.
How are they similar?
2. The alkene (CH3)2CHCH2CH=CH2 is named 4-methyl-1-pentene. What
is the name of (CH3)2CHCH2C≡CH?
3. Draw the structure for each compound.
i. 1. acetylene
ii. . 3-methyl-1-hexyne
4. Draw the structure for each compound.
i. 4-methyl-2-hexyne
ii. 3-octyne
5. Name each alkyne.
i. CH3CH2CH2C≡CH
ii. ii.CH3CH2CH2C≡CCH3

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