Chapter 9 Organic chemistry: The Infinite Varietyof Carbon

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Chapter 12

Organic Chemistry: The Infinite

Variety of Carbon Compounds

Organic Chemistry

• Chemistry of carbon-containing compounds

• Most of these come from living things

– Not necessarily the case

• ~30 million chemical compounds known

– 95% are compounds made of carbon

Chapter 9 2

Carbon

• Able to bond strongly to other carbon atoms

– Forms long chains

– Very few other atoms can form short chains, let alone long chains

• Capable of forming ring structures

• Bonds strongly to other elements

– In particular, H, O, and N

Chapter 9 3

Hydrocarbons

• Made of carbon and hydrogen

• Several classes

• Alkanes

– Contain only single bonds

– Saturated hydrocarbons

– Each C atom bonded to maximum number of H atoms

Chapter 9 4

Alkanes

• Chemical formula C n n = 1, 2, 3, …

H

2 n +2

• CH

4

, methane, simplest one

• C

2

H

6

, ethane

• All have – ane ending

– Follow a pattern

Chapter 9 5

• Condensed structural formulas

– Show how many hydrogens are attached to each carbon

CH

3

-CH

3 for ethane

• Structural formulas show how atoms are bonded together

Chapter 9 6

Isomerism

• Isomers: compounds with same molecular formula but different structural formulas

• Differences in structure may give rise to differences in chemical and physical properties

Chapter 9 7

• Number of possible isomers increases rapidly with the number of carbons

– C

30

H

62

– >4 billion possible isomers

Chapter 9 8

Chapter 9 9

Properties of Alkanes

• Main property: will burn

Chapter 9 10

Cyclic Hydrocarbons

• Carbon atom chains in form of rings

• Can be represented by structural formulas or symbolic representations

Chapter 9 11

Unsaturated Hydrocarbons

• Can have more hydrogen atoms added

• Very important in biological systems

• Alkene: hydrocarbon that contains one or more carbonto-carbon double bonds

– General formula of C n

H n

• Simplest: ethylene, C

2

H

4

Chapter 9 12

• Alkyne: hydrocarbon that contains one or more carbon-to-carbon triple bonds

• General formula of C n

H

2 n –

2

• Simplest: acetylene, C

2

H

2

Chapter 9 13

Properties of Alkenes and Alkynes

• Similar physical properties to alkanes

• Undergo more reactions than alkanes

– Addition reaction: add compounds across double bond

– Importantly, they can form polymers

Chapter 9 14

Aromatic Hydrocarbons

• Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons

H • Benzene: C

6

H

6

• Used mainly as solvents

H H

Chapter 9

H

H

15

H

Chlorinated Hydrocarbons

• Add Cl to hydrocarbons

– Increase reactivity of alkanes

• Dissolve fats, oils, and greases

– Useful for dry cleaning

• Tend to accumulate in fatty tissues

– If toxic, this will be a problem

Chapter 9 16

Chlorofluorocarbons and

Fluorocarbons

• Tend to be either liquids or gases

• Completely inert

– Except in upper atmosphere

• O

2 soluble in fluorinated compounds

– Temporary substitute for hemoglobin

Chapter 9 17

Functional Groups

• Group of atoms that gives a family of organic compounds its characteristic chemical and physical properties

• Alkyl group: derived from alkane by removing a H

– R stands for alkyl group in general

Chapter 9 18

Chapter 9 19

• –OH group

Alcohol Family

• Replace e with ol

• CH

3

OH, methanol, simplest

• Produced industrially

– Mainly a chemical intermediate

Chapter 9 20

• C

2

H

5

OH, ethanol

• Made industrially and by fermentation

– Industrially produced alcohol has noxious substances added

• Small, simple alcohols tend to be toxic

Chapter 9 21

Multifunctional Alcohols

• Several common alcohols have more than one –OH group

• Ethylene glycol: main ingredient in antifreeze

• Glycerol: used in lotions

– Ingredent in some explosives

Chapter 9 22

Phenol

• –OH group on benzene ring

– Different chemical properties than other alcohols

– Behaves more like an acid

• First antiseptic

– Also causes skin irritation

OH

Chapter 9 23

Ethers

• Two alkyl groups attached to same O

– Example CH

3

CH

2

-O-CH

2

CH

3

• Used mainly as solvent

• Little chemical reactivity

– Insoluble in water

– Highly flammable

Chapter 9 24

Chapter 9 25

Aldehydes and Ketones

• Both contain carbonyl group (C=O)

• Aldehyde: R-CHO

• Ketone: R-CO-R’

Chapter 9 26

Common Aldehydes

• Change e ending to al

• Produced by oxidation of alcohols

• Formaldehyde – used as a preservative

• Larger ones used as fragrances

– Benzaldehyde – flavor in maraschino cherries

O

C H

Chapter 9 27

Common Ketones

• Change e ending to one

• Acetone most common ketone

– Used primarily as a solvent

• Produced by oxidation of alcohols

O

H

3

C

C

Chapter 9

CH

3

28

Chapter 9 29

Carboxylic Acid

• Contains C=O and –OH group on same carbon

• Change e to oic acid

• Acetic acid: acid in vinegar

O

R C

Chapter 9

OH

30

Chapter 9 31

Esters

• Derived from carboxylic acids and alcohols

• Tend to be fragrant

– Methyl butyrate

– Ethyl butyrate

– Ethyl formate

– Methyl salicylate apple pineapple rum wintergreen

Chapter 9 32

Amines

• Contain N

• May have 1, 2, or 3 alkyl or aromatic groups

• Most biological amines are amino acids

– Building blocks of proteins

Chapter 9 33

R

Amides

• N bonded directly to carbonyl group

O

• Linkage that holds proteins together

R''

N

R'

Chapter 9 34

Heterocyclic Compounds

• Ring compounds that have something other than C in the ring

• Occur in plants

– Alkaloids: basic in solution

– Examples: caffeine, morphine, cocaine

• Form basic structure of DNA

Chapter 9 35

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