Chapter 1

Introduction to Organic Chemistry

1.1. Introduction

Organic chemistry deals with the study of substances obtained from natural or living
sources. Over time, combustion analysis established that the compounds derived from natural
sources contained carbon, and a new definition of organic chemistry emerged: Organic chemistry
is the study of carbon compounds. This is the definition we still use today.

This chapter presents and discusses the classification of organic compounds, naming and
writing formulas and relationship of structure and properties. The properties of an organic
compound depend on the atoms it contains and the way these atoms are connected. It is a very
powerful idea that someone who is trained in chemistry can look at the structural formula of a
substance and tell you a lot about its properties. This chapter begins your training toward
understanding the relationship between structure and properties of organic compounds.

1.2. Intended Learning Outcomes

At the end of this chapter, the students should be able to:

✓ Classify organic compounds

✓ Give the IUPAC names of organic compounds

✓ Draw the structures of organic compounds

✓ Determine the relative solubility of organic compounds

✓ Arrange the compounds according to increasing melting points

✓ Arrange the compounds according to increasing boiling points

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1.3. Organic Compounds and their Classification

Organic compounds are carbon containing compounds. They are classified based on their
functional groups.

Table 1. Classes of Organic Compounds

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 Table 1. Classes of Organic Compounds (continued)

Source: Organic Chemistry, McMurry (2019)

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Sample Problem:

Answers:

(a) Sulfide, Amino group, Carboxyl group

(b) Carboxyl group, Carbon-carbon double bond

(c) Ether, hydroxyl, carboxamide/amide, Carbon-carbon double bond

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Exercise:

1.4. Naming of Organic Chemistry

The system of naming organic compounds is developed by the International Union of Pure
and Applied Chemistry (IUPAC, usually spoken as eye-you-pac).

A chemical name typically has four parts in the IUPAC system of nomenclature: prefix,
parent, locant, and suffix. The prefix identifies the various substituent groups in the molecule, the
parent selects a main part of the molecule and tells how many carbon atoms are in that part, the
locants give the positions of the functional groups and substituents, and the suffix identifies the
primary functional group.

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Table 2. Root Word Use for Parent Name

# of Carbon Root word

1 meth

2 eth

3 prop

4 but

5 pent

6 hex

7 hept

8 oct

9 non

10 dec

11 undec

12 dodec

13 tridec

Table 3. Names of alkyl substitutents

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Table 4. IUPAC Names of Unbranched Alkanes

Common Names of Simple Alkyl groups

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1.4.1. Naming and Writing Structures of substituted Alkanes

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Converting a Chemical Name into a Structure

Problem

Draw the structural formula of 3-isoprpyl-2-methylhexane

First, draw the carbon skeleton of parent chain Hexane.

Laboratory Exercise

1.

2.

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3.

1.4.2. Naming and Writing Structures of Alkenes

Table 5. Common names of some alkanes

Sample problem:

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Answer:

Old IUPAC name New IUPAC name

a. 3,4,4-Trimethyl-1-butene 3,4,4-Trimethylbut-1-ene

b. 3-Methyl-3-hexene 3-Methylhex-3-ene

c. 4,7-Dimethyl-2,5-octadiene 4,7-Dimethylocta-2,5-diene

d.

Try This

1.

2.

1.4.3. Naming and Writing Structures of Alkynes

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Sample Problem:

Answer (a) 2,5-Dimethyl-3-hexyne or 2,5-Dimethylhex-3-yne

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Try (b) to (f)

1.4.4. Naming and Writing Structures of Alkyl Halides

Sample Problem:

Name the following compounds:

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Answer (a) 3,4-Dibromo-2,6-dimethylheptane
Try (b) to (e)

1.4.5. Naming and Writing Structures of Alcohols

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Common Names of Some Alcohols

Sample Problems:

1.

Answer (a) 5-Methyl-2,4-hexanediol or 5-Methylhexane-2,4-diol

1.4.6. Naming and Writing Structures of Ethers

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Sample Problem:

Answer (a) Diisopropyl ether

Table 6. Naming of Carbonyl Compounds

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1.4.7. Naming and Writing Structures of Aldehydes

Table 7. Common Names of Some Aldehydes

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1.4.8. Naming and Writing Structures of Ketones

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Sample Problem:

Answer (a) 2-Methyl-3-pentanone or 2-Methylpentan-3-one

Answer (a)

Try (b) to (f)

1.4.9. Naming and Writing Structures of Carboxylic Acids

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1.4.10. Naming and Writing Structures of Nitriles

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Sample Problem:

Answer (a) 3-Methylbutanoic acid

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1.4.11. Naming and Writing Structures of Acid Halide

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Sample Problem:

Answer (a) 4-Methylpentanoyl chloride

1.5. Solubility of Organic Compounds

Generally, organic compounds are soluble in organic solvents and have limited solubility
in water. Solubility of organic compounds depends on the intermolecular force (IMF) of attraction
between solute and solvent particles. IMF depends on the functional groups and chain length.

Let us examine the relative solubility of the given organic compounds in water.

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 Based on our examination of the data presented above, we can deduce the following:
1. Hydrocarbon chains are non-polar and do not form bonds with water molecules. They
are said to be hydrophobic (water fearing).
2. Some functional groups form hydrogen bonds with water, allowing the molecule to
dissolve. These groups are said to be hydrophilic (water loving).

Refer to the following to predict the solubility of organic compounds:

The hydrocarbon chain is hydrophobic, consequently alkanes, alkenes and alkynes do not
dissolve in water. They dissolve in non-polar solvents, such as benzene and tetrachloromethane.

Halogenoalkanes or alkyl halides are polar, but only form weak bonds with water
molecules, not enough to confer solubility. Lower members of the halgenoalkanes are slightly
soluble and this is also affected by the nature of the halogenoalkane, with tertiary halogenoalkanes
being more soluble than secondary, which in turn are more soluble than primary halogenoalkanes.

The alcohol, -OH, group is polar and able to form hydrogen bonds with water
molecules. This means that alcohols are soluble. However, as the relative molecular mass
increases, ascending the homologous series, the hydrophobic hydrocarbon chain begins to
hinder the solubility process. The result is that methanol and ethanol are miscible in all
proportions with water, but the solubility decreases on ascending the series.

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 The -COOH group forms strong hydrogen bonds with water and dissociates partially in
solution releasing free hydrogen ions. This makes carboxylic acids soluble. Once again, large
hydrocarbon chains reduce the solubility for carboxylic acids with high relative molecular
masses. The benzene carboxylic acid is only slightly soluble.

Aldehydes and Ketones both contain a highly polar carbonyl group -CO, that forms
reasonably strong bonds with water molecules. This means that the lower members of the
aldehydes and ketones are miscible with water in all proportions but the solubility decreases as
the hydrocarbon chain length increases.

Nitrogen is less electronegative than oxygen, but has a high enough electronegative
value to produce hydrogen bonding when hydrogen atoms are directly attached to the nitrogen.
Ammonia, for instance, is extremely soluble in water; the lone pair available on the nitrogen
atom attracting hydrogen atoms on neighbouring ammonia molecules. Amines are likewise
soluble. Amides also have hydrogen atoms attached directly to the nitrogen atoms and the added
advantage of electronegative oxygen atoms with available lone pairs of electrons. Hence,
amides are even more soluble. As the carbon chain increases with both amines and amides, the
solubility decreases proportionally.

1.6. Boiling Point of Organic compounds

The boiling points reflect the strength of forces between molecules. The more they stick together,
the more energy it will take to blast them into the atmosphere as gases. Most of the organic solvents
are highly volatile. They have low boiling points. There are 3 important trends to consider in
determining the relative boiling points of organic compounds.

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1. The relative strength of the four intermolecular forces is: Ionic > Hydrogen bonding > dipole
dipole > Van der Waals dispersion forces. The influence of each of these attractive forces will
depend on the functional groups present.

2. Boiling points increase as the number of carbons is increased. For molecules with a given
functional group, boiling point increases with molecular weight.

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3. Branching decreases boiling point.

1.7. Melting Point of Organic compounds

The melting point is an important physical property of a compound. The melting point can
be used to identify a substance and as an indication of its purity. The melting point of solid is
defined as the temperature at which the solid exists in equilibrium with its liquid under an external
pressure of one atmosphere.

Let us examine the relative melting points of common organic compounds.

Just like with boiling points, the relative strength of the four intermolecular forces is: Ionic
> Hydrogen bonding > dipole dipole > Van der Waals dispersion forces, greatly influence the
melting point points of organic compounds.

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 The presence of polar and hydrogen-bonding groups on organic compounds generally
leads to higher melting points. The size of a molecule and its degree of branching also affect its
melting point

End of Chapter Test

1. Complete the following table: (30pts)

Structural Formula Common name New IPAC name Old IUPAC name

p-Phthalic acid

Hexanedioic acid

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 Β-hydroxyvaleric acid

Phenyl 3-
hydroxybenzoate

Acetic butyric
anhydride

diisopropylketone

enanthaldehyde

N-butyl-2-methyl
propanamide

4-octen-2-yne

4-hydroxy-2-methyl-
6-octen-3-one

2. Arrange the following according to increasing order of solubility in water (5pts)

A. Hexanoic acid

B. Hexanal

C. Hexanol

D. Hexylbromide

E. hexane

3. Arrange the following according to increasing order of boiling point (5pts)

A. N-pentyl alcohol

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 B. Isopentyl alcohol

C. Neopentyl alcohol

D. Heptanol

E. Isopropyl alcohol

4. Arrange the following according to increasing order of melting point (5pts)

A. Decanoic acid

B. Methyl decanoate

C. Decanamide

D. Decanol

E. Decanamine

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