Introduction To Organic Chemistry

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Introduction to organic chemistry

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1.1. Introduction to organic chemistry


LEARNING OBJECTIVES

1. Define organic chemistry.


2. Identify organic molecules as alkanes, alkenes, alkynes, alcohols, or carboxylic
acids.

Organic chemistry is the study of the chemistry of carbon compounds. Carbon is singled
out because it has a chemical diversity unrivaled by any other chemical element. Its
diversity is based on the following:

 Carbon atoms bond reasonably strongly with other carbon atoms.


 Carbon atoms bond reasonably strongly with atoms of other elements.
 Carbon atoms make a large number of covalent bonds (four).

Curiously, elemental carbon is not particularly abundant. It does not even appear in
the list of the most common elements in Earth’s crust. Nevertheless, all living
things consist of organic compounds.

Most organic chemicals are covalent compounds, which is why we introduce organic
chemistry here. By convention, compounds containing carbonate ions and bicarbonate
ions, as well as carbon dioxide and carbon monoxide, are not considered part of organic
chemistry, even though they contain carbon.

The simplest organic compounds are the hydrocarbons, compounds composed of


carbon and hydrogen atoms only. Some hydrocarbons have only single bonds and
appear as a chain (which can be a straight chain or can have branches) of carbon
atoms also bonded to hydrogen atoms. These hydrocarbons are called alkanes
(saturated hydrocarbons). Each alkane has a characteristic, systematic name
depending on the number of carbon atoms in the molecule. These names consist of a
stem that indicates the number of carbon atoms in the chain plus the ending –ane. The
stem meth– means one carbon atom, so methane is an alkane with one carbon atom.
Similarly, the stem eth– means two carbon atoms; ethane is an alkane with two carbon
atoms. Continuing, the stem prop– means three carbon atoms, so propane is an alkane
with three carbon atoms. Figure 1.1. “Formulas and Molecular Models of the Three
Simplest Alkanes” gives the formulas and the molecular models of the three simplest
alkanes. (For more information about alkanes, see section 3.3.)
Uses for alkanes

The simplest alkane is methane (CH4), a colorless, odorless gas that is the major
component of natural gas. Other simple alkanes are used as fuels and solvents.
Number of Boiling
Molecular
Name Carbon Condensed Structural Formula Point Uses
Formula
Atoms (°C)

methane 1 CH4 CH4 −162 natural gas constituent

ethane 2 C2H6 CH3CH3 −89 natural gas constituent

propane 3 C3H8 CH3CH2CH3 −42 bottled gas

butane 4 C4H10 CH3CH2CH2CH3 or CH3(CH2)2CH3 0 lighters, bottled gas

pentane 5 C5H12 CH3(CH2)3CH3 36 solvent, gasoline

hexane 6 C6H14 CH3(CH2)4CH3 69 solvent, gasoline

heptane 7 C7H16 CH3(CH2)5CH3 98 solvent, gasoline

octane 8 C8H18 CH3(CH2)6CH3 126 gasoline

nonane 9 C9H20 CH3(CH2)7CH3 151 gasoline

decane 10 C10H22 CH3(CH2)8CH3 174 kerosene

Table: The First 10 Straight-Chain Alkanes

Figure 1.1. Formulae and molecular models of the three simplest alkanes
The three smallest alkanes are methane, ethane, and propane.

Some hydrocarbons have one or more carbon–carbon double bonds (denoted C=C).
These hydrocarbons are called alkenes (see section 3.2. for more information) Note
that the names of alkenes have the same stem as the alkane with the same number of
carbon atoms in its chain but have the ending –ene. Thus, ethene is an alkene with two
carbon atoms per molecule, and propene is a compound with three carbon atoms and
one double bond.

Figure 1.2. Formulas and Molecular Models of the Two Simplest Alkenes

Ethene is commonly called ethylene, while propene is commonly called propylene.


Alkynes are hydrocarbons with a carbon–carbon triple bond (denoted C≡C) as part of
their carbon skeleton (see section 3.2. for more information). The names for alkynes
have the same stems as for alkanes but with the ending –yne.

Figure 1.3. Formulas and Molecular Models of the Two Simplest Alkynes

Ethyne is more commonly called acetylene.

To your health: saturated and unsaturated fats

Hydrocarbons are not the only compounds that can have carbon–carbon double bonds.
A group of compounds called fats can have them as well, and their presence or
absence in the human diet is becoming increasingly correlated with health issues.

Fats are combinations of long-chain organic compounds (fatty acids) and glycerol
(C3H8O3). The long carbon chains can have either all single bonds, in which case the fat
is classified as saturated, or one or more double bonds, in which case it is
a monounsaturated or a polyunsaturated fat, respectively. Saturated fats are typically
solids at room temperature; beef fat (tallow) is one example. Mono- or polyunsaturated
fats are likely to be liquids at room temperature and are often called oils. Olive oil,
flaxseed oil, and many fish oils are mono- or polyunsaturated fats.

Some studies have linked higher amounts of saturated fats in people’s diets with a
greater likelihood of developing heart disease, high cholesterol, and other diet-related
diseases. In contrast, increases in unsaturated fats (either mono- or polyunsaturated)
have been linked to a lower incidence of certain diseases. Thus, there have been
recommendations by government bodies and health associations to decrease the
proportion of saturated fat and increase the proportion of unsaturated fat in the diet.
Most of these organizations also recommend decreasing the total amount of fat in the
diet. A difference as simple as the difference between a single and double carbon–
carbon bond can have a significant impact on health.

The carbon–carbon double and triple bonds are examples of functional groups in
organic chemistry. A functional group is a specific structural arrangement of atoms or
bonds that imparts a characteristic chemical reactivity to a molecule. Alkanes have no
functional group, and they are mostly inert (unreactive). A carbon–carbon double bond
is considered a functional group because carbon–carbon double bonds chemically react
in specific ways that differ from reactions of alkanes (for example, under certain
circumstances, alkenes react with water); a carbon–carbon triple bond also undergoes
certain specific chemical reactions. In the remainder of this section, we introduce two
other common functional groups.

If an OH group (also called a hydroxyl group) is substituted for a hydrogen atom in a


hydrocarbon molecule, the compound is an alcohol. Alcohols are named using the
parent hydrocarbon name but with the final –e dropped and the suffix –ol attached. The
two simplest alcohols are methanol and ethanol (see Figure 1.4.).

Figure 1.4. The two simplest organic alcohol compounds

Alcohols have an OH functional group in the molecule. Ethanol (also called ethyl
alcohol) is the alcohol in alcoholic beverages. Other alcohols include methanol (or
methyl alcohol), which is used as a solvent and a cleaner, and 2-propanol (also called
isopropyl alcohol or rubbing alcohol), which is used as a medicinal disinfectant. Neither
methanol nor isopropyl alcohol should be ingested, as they are toxic even in small
quantities. Cholesterol is an example of a more complex alcohol.

Another important family of organic compounds has a carboxyl group, in which a carbon
atom is double-bonded to an oxygen atom and to an OH group. Compounds with a
carboxyl functional group are called carboxylic acids, and their names end in –oic acid.
The two simplest carboxylic acids are shown in Figure 1.5. They are perhaps best
known by the common names formic acid (found in the stingers of ants) and acetic
acid (found in vinegar). The carboxyl group is sometimes written in molecules as
COOH.
Figure 1.5. The two smallest organic acids

Many organic compounds are considerably more complex than the examples described
here. Many compounds contain more than one functional group. The formal names can
also be quite complex. In section 1.6. we will examine functional groups in more detail,
and we will learn about the system of naming (nomenclature) for hydrocarbons
in chapter 3.

EXAMPLE 1

Identify the functional group(s) in each molecule as a double bond, a triple bond, an
alcohol, or a carboxyl.

1. CH3CH2CH2CH2OH

2.

3.
4.

Solution

1. This molecule has an alcohol functional group.


2. This molecule has a double bond and a carboxyl functional group.
3. This molecule has an alcohol functional group.
4. This molecule has a double bond and a carboxyl functional group.

Skill-building exercise

Identify the functional group(s) in each molecule as a double bond, a triple bond, an
alcohol, or a carboxyl.

1.

2.

3.

4.
Concept review exercises

1. What is organic chemistry?


2. What is a functional group? Give at least two examples of functional groups.

Answers

1. Organic chemistry is the study of the chemistry of carbon compounds.


2. A functional group is a specific structural arrangement of atoms or bonds that
imparts a characteristic chemical reactivity to the molecule; alcohol group and
carboxylic group (answers will vary).

Key takeaways

 Organic chemistry is the study of the chemistry of carbon compounds.


 Organic molecules can be classified according to the types of elements and bonds
in the molecules.

Exercises

1. Give three reasons why carbon is the central element in organic chemistry.
2. Are organic compounds based more on ionic bonding or covalent bonding?
Explain.
3. Identify the type of hydrocarbon in each structure.
1.

2.

3.
4.

4. Identify the type of hydrocarbon in each structure.


1.

2.

3.

4.

5. Identify the functional group(s) in each molecule.


1.
2.

3.

4.

6. Identify the functional group(s) in each molecule.


1.

2.
3.

4.

7. How many functional groups described in this section contain carbon and
hydrogen atoms only? Name them.
8. What is the difference in the ways the two oxygen atoms in the carboxyl group are
bonded to the carbon atom?

Answers

1. Carbon atoms bond reasonably strongly with other carbon atoms. Carbon atoms
bond reasonably strongly with atoms of other elements. Carbon atoms make a
large number of covalent bonds (four).
2.
3.
1. alkane
2. alkene
3. alkene
4. alkyne
4.
5.
1. alcohol
2. carboxyl
3. alcohol
4. carbon-carbon double bond and carbon-carbon triple bond
6.
7. two; carbon-carbon double bonds and carbon-carbon triple bonds

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