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

Chapter 1: Structure and Physical Properties of Organic Compounds

Chapter 2: Reactions of Organic Compounds

UNIT 1: Organic Chemistry


UNIT 1 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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1.1 Introducing Organic Compounds

UNIT 1 Section 1.1

• 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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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.

UNIT 1 Section 1.1

The Special Nature of the Carbon Atom

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

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• Constitutional or structural isomers: molecules with the same molecular formula, but the atoms are bonded in a different sequence.

UNIT 1 Section 1.1

Isomers

These molecules are constitutional isomers.

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• 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.


Stereoisomers: molecules with the same molecular formula and sequence of atoms, but they differ in the three-dimensional orientation of their atoms

UNIT 1 Section 1.1

These molecules are diastereomers.

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• diastereomer: stereoisomers based on the presence of a double bond

• enantiomer: stereoisomers that are mirror-images of each other.


Isomers

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

UNIT 1 Section 1.1

Answer on the next slide


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LEARNING CHECK

Yes they are isomers.

They are stereoisomers, not constitutional isomers.

Section 1.1UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds

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LEARNING CHECK

Section 1.1 Review

UNIT 1 Section 1.1Chapter 1: Structure and Physical Properties of Organic Compounds

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1.2 Hydrocarbons

UNIT 1 Section 1.2

• aromatic hydrocarbons

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

• alkanes

• alkenes

• cyclic hydrocarbons

• alkynes

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Drawing Hydrocarbons

UNIT 1 Section 1.2

• line structural formula

Five ways to represent hydrocarbon molecules are:

• empirical molecular formula

• expanded molecular formula

• condensed structural formula

• structural formula

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UNIT 1 Section 1.2

Alkanes

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• 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.


UNIT 1 Section 1.2

Alkenes

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• 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-ethyl-2,2-dimethylhex-1-ene.


Name the following hydrocarbon and draw its condensed structural formula.

UNIT 1 Section 1.2



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LEARNING CHECK

The name is: pent-2-ene

The condensed structural formula is:


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LEARNING CHECK

UNIT 1 Section 1.2

Alkynes

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• 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.


UNIT 1 Section 1.2

Cyclic Hydrocarbons

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• 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


UNIT 1 Section 1.2

Aromatic Hydrocarbons

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• 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.


A student has named a hydrocarbon as1-ethyl-5-propylbenzene.

Use a drawing of the structure to show why that name is incorrect.

What is the correct name?

UNIT 1 Section 1.2



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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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LEARNING CHECK

UNIT 1 Section 1.2

Physical Properties of Hydrocarbons

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• Hydrocarbons are non-polar (not soluble in water).

• The shapes and sizes of hydrocarbons affect their boiling points.

• Many aromatic compounds have strong odours.


Section 1.2 Review


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1.3 Hydrocarbon Derivatives

UNIT 1 Section 1.3

Hydrocarbon derivatives have one or more functional groups.

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Hydrocarbon Derivatives

UNIT 1 Section 1.3

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UNIT 1 Section 1.3

Alcohols

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• 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.


UNIT 1 Section 1.3

Haloalkanes

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• 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


Draw the structural formula for fluoroethane.

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

UNIT 1 Section 1.3



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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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LEARNING CHECK

UNIT 1 Section 1.3

Aldehydes

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• Contain a formyl group.

3,4-dimethylpentanal

• 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)


UNIT 1 Section 1.3

Ketones

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• 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)


Butanone


UNIT 1 Section 1.3

Carboxylic Acids

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• Contain a carboxyl group.

2-ethylhexanoic acid

• When naming and drawing carboxylic acids, identify the• root (longest chain with the carboxyl group)• suffix (ends in –oic acid )



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

Section 1.3UNIT 1



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LEARNING CHECK

The carbonyl group

Section 1.3UNIT 1

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LEARNING CHECK

UNIT 1 Section 1.3

Esters

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• 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)


UNIT 1 Section 1.3

Ethers

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• Contain an oxygen atom singly bonded to two carbon atoms (R-O-R′)

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

• 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)


UNIT 1 Section 1.3

Amines

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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)


UNIT 1 Section 1.3

Amides

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• 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)


Draw the condensed structural formula for each of the following:

a.Methylethanoate

b. 1-ethoxypropane

c. N-ethylpentamide

UNIT 1 Section 1.3



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LEARNING CHECK

a.

b.

c.


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LEARNING CHECK

Section 1.3 Review


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Documents

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