UNIT 1: Organic Chemistry

Chapter 1: Structure and Physical Properties of Organic Compounds Chapter 2: Reactions of Organic Compounds

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Chapter 1: Structure and Physical Properties of Organic Compounds

Chapter 1: Structure and Physical Properties of Organic Compounds

For thousands of years, scientists and Aboriginal peoples have been isolating organic compounds from natural materials, such as birch bark. The properties of these compounds make them useful in a wide variety of applications.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

1.1 Introducing Organic Compounds

Until the late 1800s, organic meant matter from living systems. Inorganic meant matter from non-living systems. Synthesis of urea (organic) from inorganic compounds forced scientists to reconsider their definitions.

Modern Definitions

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

The Special Nature of the Carbon Atom

Important atomic properties of carbon: It is much more likely to share electrons than gain or lose electrons. Therefore, covalent bonding occurs. It has four valence electrons. Therefore, it can be bonded to as many as four different atoms.

Carbon can bond to four different atoms, producing a molecule with a tetrahedron shape.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

Isomers
Most organic molecules consist of more than one carbon atom bonded together in a chain or ring structure. Molecules with the same molecular formula but atoms in different arrangements are known as isomers. Constitutional or structural isomers: molecules with the same molecular formula, but the atoms are bonded in a different sequence.

These molecules are constitutional isomers.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

Isomers
Stereoisomers: molecules with the same molecular formula and sequence of atoms, but they differ in the three-dimensional orientation of their atoms diastereomer: stereoisomers based on the presence of a double bond enantiomer: stereoisomers that are mirror-images of each other.
These molecules are diastereomers.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

LEARNING CHECK
Are the following molecules isomers? If so, what type of isomers are they?

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

LEARNING CHECK
Yes they are isomers.
They are stereoisomers, not constitutional isomers.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.1

Section 1.1 Review

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

1.2 Hydrocarbons
Hydrocarbons are composed of only carbon and hydrogen. The different classes are:

cyclic hydrocarbons
alkanes

alkenes

aromatic hydrocarbons

alkynes
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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Drawing Hydrocarbons
Five ways to represent hydrocarbon molecules are:

empirical molecular formula

condensed structural formula

expanded molecular formula

line structural formula

structural formula

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Alkanes
Contain only single covalent bonds. The general formula for straight and branched-chain alkanes: CnH2n+2. When naming and drawing alkanes: identify the root, suffix, and prefix.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Alkenes
Contain one or more double bonds. The general formula for straight and branched-chain alkenes: CnH2n. When naming and drawing alkenes: identify the root, suffix and prefix.
For main chains with more than four carbons, the position of the double bond must be indicated.

This alkene is named 3-ethyl2,2-dimethylhex-1-ene.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

LEARNING CHECK
Name the following hydrocarbon and draw its condensed structural formula.

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

LEARNING CHECK
The name is: pent-2-ene The condensed structural formula is:

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Alkynes
Contain one or more triple bonds. The general formula for straight and branched-chain alkynes: CnH2n-2. When naming and drawing alkynes: identify the root, suffix, and prefix.
For main chains with more than four carbons, the position of the double bond must be indicated.

4-ethylhex-2-yne.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Cyclic Hydrocarbons
Contain carbon-based ring structures. Most are alkanes or alkenes. The general formula for cyclic alkanes: CnH2n. When naming and drawing cyclic hydrocarbons: identify the root, suffix, and prefix.
Carbon atoms of a multiple bond are numbered 1 and 2, and side groups are the lowest possible numbers.

3,4-dimethylcyclopentene

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Aromatic Hydrocarbons
Hydrocarbons that are derived from benzene, C6H6. When naming and drawing aromatic hydrocarbons identify the root and prefix. If a benzene ring is bonded to a hydrocarbon chain that is more than six carbons long, the benzene ring is a phenyl side group.
Benzene is best represented by the resonance hybrid structure. This aromatic hydrocarbon is 1-methyl-4-propylbenzene.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

LEARNING CHECK
A student has named a hydrocarbon as 1-ethyl-5-propylbenzene. Use a drawing of the structure to show why that name is incorrect. What is the correct name?

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

LEARNING CHECK
The structure is shown below. Since the side groups should be identified using the lowest possible numbering, the correct name is 1-ethyl-3-propylbenzene

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Physical Properties of Hydrocarbons

Hydrocarbons are non-polar (not soluble in water). The shapes and sizes of hydrocarbons affect their boiling points. Many aromatic compounds have strong odours.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.2

Section 1.2 Review

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

1.3 Hydrocarbon Derivatives

Hydrocarbon derivatives have one or more functional groups.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Hydrocarbon Derivatives

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Alcohols
Contain a hydroxyl functional group, -OH When naming and drawing alcohols, identify the
root (longest chain with the OH group) suffix (add ol to the end of the parent alkane name) prefix (name and number the alkyl side groups)

The addition of an OH group to a hydrocarbon increases the polarity of the molecule.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Haloalkanes
Contain one or more halogen atoms (F, Cl, Br, I). When naming and drawing haloalkanes, identify the

root (longest chain with the halogen) suffix (use the alkane name) prefix (name and number the alkyl side groups and halogens)

1,3-dichloro-3-fluoro-2methylbutane

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK
Draw the structural formula for fluoroethane.

Explain why numbers are not required in the prefix of the name.

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK

Because there are only two carbon atoms, the number 1 is not used in the prefix to designate the position of the halogen.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Aldehydes
Contain a formyl group. When naming and drawing aldehydes, identify the

root (longest chain with the formyl group) suffix (ends in al) prefix (name and number the alkyl side groups)
3,4-dimethylpentanal

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Ketones
Contain a carbonyl group bonded to two carbons. When naming and drawing ketones, identify the

root (longest chain with the carbonyl group) suffix (position of the carbonyl carbon is indicated and ends in -one)

prefix (name and number the alkyl side groups)

Butanone

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Carboxylic Acids
Contain a carboxyl group.

When naming and drawing carboxylic acids, identify the

root (longest chain with the carboxyl group) suffix (ends in oic acid ) prefix (name and number the alkyl side groups)

2-ethylhexanoic acid

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK
What functional group do aldehydes, ketones, and carboxylic acids have in common?

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK
The carbonyl group

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Esters
Contain a carbonyl group with another oxygen singly bonded to the carbon. When naming and drawing esters, identify the
root (the acid part) suffix (ends in oate )

prefix (alkyl group on oxygen and on the main chain)

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Ethers
Contain an oxygen atom singly bonded to two carbon atoms (R-O-R)
When naming and drawing ethers, identify the

root (longest chain, or R group) suffix (ends according to the main chain) prefix (indicate the alkoxy group then side groups)

An ether is composed of an alkoxy group and parent alkane chain that are connected by an oxygen.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Amines
Primary (R-NH2), secondary (R2-NH), or tertiary (R3-N) When naming and drawing amines, identify the

root (longest chain bonded to the nitrogen) suffix (ends in amine and indicate position of the N) prefix (indicate alkyl groups on N)

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Amides
Contain a carbonyl group bonded to a nitrogen

When naming and drawing amides, identify the

root (longest chain with the carbonyl) suffix (ends in -amide ) prefix (alkyl groups on N, then on main chain)

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK
Draw the condensed structural formula for each of the following:
a. Methylethanoate b. 1-ethoxypropane c. N-ethylpentamide

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Answer on the next slide

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

LEARNING CHECK
a.

b.

c.

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Chapter 1: Structure and Physical Properties of Organic Compounds

Section 1.3

Section 1.3 Review

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