Download Chapter 9 Organic chemistry: The Infinite Varietyof Carbon

Nuclear Power Plants
• Provide ~20% U.S. electricity
– France >70%
• Slow controlled release of energy
• Need 2.5–3.5% 235U
• Problem with disposal of radioactive
waste
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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
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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
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Hydrocarbons
• Made of carbon and hydrogen
• Alkanes
– Contain only single bonds
– Saturated hydrocarbons
– Each C atom bonded to maximum number of H
atoms
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Alkanes
• CH4, methane, simplest
one
• C2H6, ethane
• All have –ane ending
– Follow a pattern
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Methane, CH4.
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• structural formulas
– Show how many hydrogens are attached
to each carbon
CH3-CH3 for ethane
• Structural formulas show how atoms are
bonded together
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Methane and the tetrahedral carbon.
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PPRRExample 9.1 Kinds of Hydrocarbon Formulas
Problems
Give the structural formula for heptane.
Give the structural formula for
octane.
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Properties of Alkanes
• Main property: will burn and nonpolar
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© 2003 John Wiley and Sons Publishers
Courtesy Andy Washnik
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Gasoline, mineral oil, lubricating oil and petroleum jelly.
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Chapter 9
: Cycloalkanes.
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Unsaturated Hydrocarbons
• Very important in biological
systems
• Alkene: hydrocarbon that
contains one or more carbonto-carbon double bonds
• Simplest: ethylene, C2H4
• ethylene used for ripening fruit
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Properties of Alkenes
• Similar physical properties to alkanes
• Undergo more reactions than alkanes
– Addition reaction: add compounds across
double bond
– Importantly, they can form polymers
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Properties of Alkenes
• Main property: will burn, nonpolar and
more reactive
• Long chained hydrocarbon will be liquid
rather than solid
• example turkey fat and vegetable oil
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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
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Chlorofluorocarbons and
Fluorocarbons
• Tend to be either liquids or gases
• Completely inert
– Except in upper atmosphere
• O2 soluble in fluorinated compounds
– Temporary substitute for hemoglobin
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• Discuss DDT
• Discuss Splenda
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Alcohols
Alcohols contain the hydroxyl (-OH)
functional group.
Examples include:
methanol
ethanol
1-propanol
CH3OH
CH3CH2OH
CH3CH2CH2OH
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Methanol
Methanol or methyl
alcohol is sometimes
called wood alcohol. It
is an important solvent
and automotive fuel
additive and possible
fuel replacement.
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Ethanol
Ethanol or ethyl
alcohol is also known
as grain alcohol. It is
the alcohol of alcoholic
beverages. It is also an
additive to automotive
fuel and is being
considered as a
gasoline replacement.
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Toxicity of Alcohols
All alcohols are toxic. Methanol for instance
is oxidized to formaldehyde by liver enzymes.
It can lead to blindness and death.
Even ethanol is toxic. The effects of drinking
ethanol are due to its toxicity. Drunk driving,
alcoholism, and fetal alcohol syndrome are all
effects due to the toxicity of ethanol.
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Ethanol
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Multifunctional Alcohols
Some alcohols contain more than one
hydroxyl group.
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Complex Alcohols
• Several common alcohols have more
than one –OH group
• Ethylene glycol: main ingredient in
antifreeze
• Glycerol: used in lotions
– Ingredient in some explosives
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Discuss gas mileage and fuels
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Carboxylic Acids
Organic acids contain the carboxyl (COOH)
functional group.
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Esters
Esters are derived from carboxylic acids and
alcohols or phenols.
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Esters
Esters generally have a pleasant odor.
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Esters
Esters are named by stating the name of the
alcohol part first followed by the name of the acid
part with the suffix –ate.
For example: Methyl butyrate
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Amines and Amides
Amines are derivatives of ammonia. When
one or more hydrogen of ammonia is
replaced by an alkyl group, an amine is the
result. Like ammonia, amines tend to be
basic and have similar odors.
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Amines and Amides
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Amines and Amides
Amides have the nitrogen bonded to a
carbonyl carbon.
The amino acids of proteins are linked by
amide linkages.
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end
• end
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Aldehydes and Ketones
• Both contain carbonyl group (C=O)
• Aldehyde: R-CHO
• Ketone: R-CO-R’
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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
O
cherries
C
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H
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Common Ketones
• Change -e ending to -one
• Acetone most common ketone
– Used primarily as a solvent
• Produced by oxidation of alcohols
O
C
CH 3
H3C
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Carboxylic Acid
• Contains C=O and –OH group on same
carbon
• Change -e to -oic acid
• Acetic acid: acid in vinegar
O
R
C
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OH
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Esters
• Derived from carboxylic acids and alcohols
• Tend to be fragrant
– Methyl butyrate
– Ethyl butyrate
– Ethyl formate
– Methyl salicylate
apple
pineapple
rum
wintergreen
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© 2003 John Wiley and Sons Publishers
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Figure 6.13: The carbon-carbon single bond
of9 ethane and the carbon-carbon double
bond of ethylene.
© 2003 John Wiley and Sons Publishers
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Figure 6.15: The conversion of unsaturated ethylene to saturated ethane.
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© 2003 John Wiley and Sons Publishers
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Figure 6.16: Adding water to an alkene produces an alcohol.
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END
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Alcohol Family
•
•
•
•
–OH group
Replace -e with -ol
CH3OH, methanol, simplest
Produced industrially
– Mainly a chemical intermediate
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• C2H5OH, ethanol
• Made industrially and by fermentation
– Industrially produced alcohol has noxious
substances added
• Small, simple alcohols tend to be toxic
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Phenol
• –OH group on benzene ring
– Different chemical properties than other
alcohols
– First antiseptic
– Also causes skin irritation
OH
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