chapter 14 lecture conceptual integrated science second edition © 2013 pearson education, inc....

Chapter 14 Lecture

ConceptualIntegrated Science

Second Edition

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OrganicCompounds

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This lecture will help you understand:

• Organic Chemistry• Hydrocarbons• Unsaturated Hydrocarbons• Functional Groups• Alcohols, Phenols, and Ethers• Amines and Alkaloids• Carbonyl Compounds• Polymers

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Organic Chemistry

• Organic chemistry is the branch of chemistry that involves the study of carbon-containing chemical compounds.

• An organic compound is a carbon-containing chemical compound. More than 13 million organic compounds are known.

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• Carbon atoms connect with one another through strong and stable covalent bonds.

Organic Chemistry

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C C C

C

C

C

N N NN

N

N

O O OO

O

O

S SS

S S

347 kJ/mol 159 kJ/mol

138 kJ/mol

226kJ/mol

Organic Chemistry

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Organic Chemistry

• Carbon atoms also readily form bonds with many other types of atoms. This provides for a nearly infinite number of different kinds of organic compounds.

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Hydrocarbons

• A hydrocarbon is a chemical compound that contains only hydrogen and carbon.

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Hydrocarbons

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• Structural isomers are molecules that have the same molecular formula but different configurations.

Hydrocarbons

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• A configuration is the specific way in which the atoms of a molecule are connected to one another.

"configuration" = "connectivity"• Conformation is the spatial orientation of a single

configuration.

Hydrocarbons

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C7H16

C8H18

C10H22

C20H42

C6H14

C5H12

9

18

75

366,319

5

3

Formula

Number of possible isomers

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What is the chemical formula for the following structure?

A. C3H8

B. C4H10

C. C5H12

D. C6H14

Explain your answer to your neighbor.

HydrocarbonsCHECK YOUR NEIGHBOR

cc

cc

c

H

HH

HH

HH

H

H

HH

H

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What is the chemical formula for the following structure?

A. C3H8

B. C4H10

C. C5H12

D. C6H14

HydrocarbonsCHECK YOUR ANSWER

H

cc

cc

c

H

HH

HH

HH

H

H

HH

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Hydrocarbons

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• Carbon always forms four bonds.

Unsaturated Hydrocarbons

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• Some of carbon's four bonds, however, may be within multiple bonds.

Unsaturated Hydrocarbons

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• An unsaturated hydrocarbon is a hydrocarbon that contains one or more multiple bonds.– A special case of an unsaturated hydrocarbon

is the benzene ring.

Unsaturated Hydrocarbons

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What is the chemical formula for the following structure?

A. C5H10

B. C5H12

C. C6H12

D. C6H14

Explain your answer to your neighbor.

Unsaturated HydrocarbonsCHECK YOUR NEIGHBOR

cc

cc

c

H

HH

HH

H

H

HH

H

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What is the chemical formula for the following structure?

• C5H10

• C5H12

• C6H12

• C6H14

Unsaturated HydrocarbonsCHECK YOUR ANSWER

cc

cc

c

H

HH

HH

H

H

HH

H

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• A heteroatom is any atom other than hydrogen or carbon in an organic molecule.

• A functional group is a combination of carbon, hydrogen, and heteroatoms that behave as a single unit.– Organic molecules are classified by the

functional groups they contain.

Functional Groups

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Functional Groups

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A. B. C. D.

Functional GroupsCHECK YOUR NEIGHBOR

In which of the following structures is carbon bonded five times?

Explain your answer to your neighbor.

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In which of the following structures is carbon bonded five times?

Explanation:

Carbon can never be bonded five times! In none of the structures is carbon indicated to be bonded five times. Sorry for the trick question…

A. B. C. D.

Functional GroupsCHECK YOUR ANSWER

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Alcohols, Phenols, and Ethers

Hydroxyl group

• Alcohols contain the hydroxyl group.

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Alcohols, Phenols, and Ethers

Methanol(bp 65°C)

Ethanol(bp 78°C)

2-Propanol(bp 97°C)

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Alcohols, Phenols, and Ethers

• Phenols contain the phenol group.

Phenol group

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Alcohols, Phenols, and Ethers

• Phenols are acidic

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Alcohols, Phenols, and Ethers

4-n-Hexylresorcinol Thymol

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Alcohols, Phenols, and Ethers

• Ethers contain the ether group, an oxygen atom bonded to two carbon atoms.

Ether group

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Alcohols, Phenols, and Ethers

Dimethyl ether(bp −25°C)

Diethyl ether

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Amines and Alkaloids

• Amines form alkaline solutions.

Amine group

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Alcohols, Phenols, and Ethers

Ethyl amine

Hydroxideion

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Alcohols, Phenols, and Ethers

Caffeine

Phosphoric acid

Caffeinesalt

Water soluble

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Which of the following compounds should have a higher boiling point?

A. Structure A

B. Structure B

C. Both should have the same boiling point.

D. There is no way to tell.

Explain your answer to your neighbor.

Amines and AlkaloidsCHECK YOUR NEIGHBOR

N

H

O

Structure A Structure B

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Which of the following compounds should have a higher boiling point?

A. Structure AB. Structure BC. Both should have the same boiling point.D. There is no way to tell.

Explanation: Structure B has a hydrogen attached to a strongly electronegative atom, nitrogen. This makes for a polar N—H bond that participates in hydrogen bonding.

Amines and AlkaloidsCHECK YOUR ANSWER

N

H

O

Structure A Structure B

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Carbonyl Compounds

• A carbonyl is a carbon atom double bonded to an oxygen atom.

Carbonyl

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Carbonyl Compounds

Ketone group

Aldehyde group

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Carbonyl Compounds

Acetone Acetaldehyde

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Carbonyl Compounds

Cinnamonaldehyde Benzaldehyde

Vanillin

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Carbonyl Compounds

Amide group

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Carbonyl Compounds

N,N-Diethyl-m-toluamide

DEET

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Carbonyl Compounds

Carboxyl group

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Carbonyl Compounds

Salicylic acid Acetylsalicylic acid

Aspirin

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Carbonyl Compounds

Ester group

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Carbonyl Compounds

Salicylic acid

H2SO4

CH3OH

Methyl salicylate

(wintergreen)

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Carbonyl Compounds

Penicillin

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The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine?

A. The hydrogen (shown) must be removed and and replaced with an amino (NH2) group.

B. Lysine is 1,5-pentanediamine. Nothinghas to be removed.

C. The carboxyl group must be removedand replaced with a hydrogen.

D. One amino group must be removed and replaced with a hydrogen.

Explain your answer to your neighbor.

Carbonyl CompoundsCHECK YOUR NEIGHBOR

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The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine?

A. The hydrogen (shown) must be removed and and replaced with an amino (NH2) group.

B. Lysine is 1,5-pentanediamine. Nothinghas to be removed.

C. The carboxyl group must be removedand replaced with a hydrogen.

D. One amino group must be removed and replaced with a hydrogen.

Carbonyl CompoundsCHECK YOUR ANSWER

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• A polymer is a very long organic molecule made by the joining together of smaller organic molecule units known as monomers.

MonomerMonomer MonomerMonomer MonomerMonomer MonomerMonomer

Polymers

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H

C CH

H

C CH

H H

H H

H

C CH

H H

H

C CH

H H

CH

H

H

CH

Polymers

• An addition polymer is a polymer whose mass is equal to the sum of the masses of the monomer units.

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H

C C

H

H

C C

H

H H

H H

H

C C

H

H H

H

C C

H

H H

C

H

H

H

C

H

Ethylene Ethylene Ethylene Ethylene EthyleneEthylene

Polyethylene

C

H

H

C

H

H

Polymers

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Polypropylene

C

H

C C

H

H

C C

H H

H

H

C C

H

H CH3

C C

H H

H

C

H H

HCH3 CH3 CH3 CH3

Propylene Propylene Propylene Propylene Propylene Propylene

H

C

H

C

H

CH3

Polymers

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Polymers

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• A condensation polymer is a polymer formed when the joining of monomer units is accompanied by the loss of a small molecule, such as water.

Polymers

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Polymers

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• Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units in the structure shown to the right.

Isoprene

(2-methyl-1,3-butadiene) Citral

Polymers

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• Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units in the structure shown to the right.

Citral

Polymers

Isoprene

(2-methyl-1,3-butadiene)

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• Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units in the structure shown below.

Beta-carotene

Isoprene

(2-methyl-1,3-butadiene)

Polymers

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Isoprene

(2-methyl-1,3-butadiene)

Beta-carotene

Polymers

• Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units in the structure shown below.