Chapter 14 organic compounds

Chapter 14: Organic Compounds

Principles of Science II

This lecture will help you understand:

• Organic Chemistry

• Hydrocarbons• Unsaturated Hydrocarbons• Functional Groups

• Alcohols, Phenols, and Ethers

• Amines and Alkaloids• Carbonyl Compounds

• Polymers

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.

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

.

Organic Chemistry

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.

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

Hydrocarbons

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

Hydrocarbons

• 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

C7H16

C8H18

C10H22

C20H42

C6H14

C5H12

9

18

75

366,319

5

3

Formula

Number of possible isomers

Hydrocarbons

• A schematic for the fractional distillation of petroleum into useful hydrocarbon components

A hydrocarbon, such as heptane, can be ignited from the heat generator as gasoline is compressed by a piston- before a spark plug fires. This upsets the timing of the

engine cycle, giving rise to a knock sound.

Branched hydrocarbons, such as isooctane, burn less readily and are ignited not by compression alone but

only when the spark plug fires.

Octane ratings are posted on gasoline pumps. The engines of modern cars are designed to run best on

87 octane grade fuel.

• Carbon always forms four bonds.

Unsaturated Hydrocarbons

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


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

the benzene ring.


• 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

Functional Groups

Alcohols, Phenols, and Ethers

Hydroxyl group

• Alcohols contain the hydroxyl group.


Methanol(bp 65°C)

Ethanol(bp 78°C)

2-Propanol(bp 97°C)


• Phenols contain the phenol group.

Phenol group


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

Ether group


Dimethyl ether(bp −25°C)

Diethyl ether

Amines and Alkaloids

• Amines form alkaline solutions.

Amine group


Ethyl amine

Hydroxideion


CaffeinePhosphoric

acid Caffeinesalt

Water soluble

Carbonyl Compounds

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

Carbonyl

Carbonyl Compounds

Ketone group

Aldehyde group

Carbonyl Compounds

Acetone Acetaldehyde

Carbonyl Compounds

Cinnamonaldehyde Benzaldehyde

Vanillin

Carbonyl Compounds

Amide group

Carbonyl Compounds

N,N-Diethyl-m-toluamide

DEET

Carbonyl Compounds

Carboxyl group

Carbonyl Compounds

Salicylic acid Acetylsalicylic acid

Aspirin

Carbonyl Compounds

Ester group

Carbonyl Compounds

Salicylic acid

H2SO4

CH3OH

Methyl salicylate(wintergreen)

Carbonyl Compounds

Penicillin

• 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

H

C CH

HC C

H

H H

H H

H

C CH

H H

H

C CH

H HCH

H

H

CH

Polymers

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

HC C

H

H

C C

H

H H

H H

HC C

H

H H

HC C

H

H H

CH

H

HC

H

Ethylene Ethylene Ethylene Ethylene EthyleneEthylene

Polyethylene

CH

H

CH

H

Polymers

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

Polymers

• 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

Polymers

• 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

• 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)

• 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


Polymers

Isoprene


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.