SLIDE 1 

Chemistry in Focus 3rd editionTro

Chapter 6Organic Chemistry

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CARBON

• Of the millions of known compounds in our world, 95% have a single element in common – CARBON.

• What is so special about carbon?

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Carbon• Smallest member, and only nonmetal, of Group 4• Forms 4 covalent bonds• Forms single, double, and triple bonds• Bonds to itself, forming rings

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• The study of carbon-containing compounds and their chemistry is called organic chemistry.

• The properties of carbon-containing molecules determine the properties of the substance they compose.

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Organic vs. Inorganic

• Early 1800s– Organic

• Came from living organisms• Chemically fragile• Unsuccessful synthesis…vital force?

– Inorganic• Came from the earth• Chemically durable• Successfully synthesized by 19th century chemists

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Urea

• Synthesized by Friedrich Wohler in 1828• Organic, but synthesized from an

inorganic compound• Subsequent death of vitalism

– The idea that life was somehow beyond physical laws was proved wrong.

– Living organisms must follow the physical laws of the universe.

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Organic Compounds

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Two Major Types ofOrganic Compounds

• Hydrocarbons– Contain only carbon and hydrogen

• Functionalized Hydrocarbons– Hydrocarbons that contain additional atoms or

groups of atoms

• Both groups can be further divided into subfamilies.

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The Hydrocarbon Family

• Alkanes– Only single bonds

• Alkenes– One or more double bonds

• Alkynes– One or more triple bonds

• Aromatic– Six-carbon rings

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Alkanes

• All carbon atoms connected by single bonds

• General molecular formula: CnH2n+2

• Simplest is methane, CH4

• Each atom attains an octet; molecular geometry of methane is tetrahedral.

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Polarity of Hydrocarbons

• Carbon-hydrogen bonds are mostly nonpolar but any polarity would be symmetrically arranged about the central carbon atom(s).

• Methane’s tetrahedral geometry makes it a nonpolar molecule.– All other hydrocarbons are nonpolar as well.

• Nonpolar substances are unable to mix with polar substances.

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Structural Formulas

• Show the relative positions of atoms in a molecule

• Two-dimensional• Similar to Lewis structures but dashes

represent bonding electron pairs• Condensed structural formulas are

compactly written structural formulas.

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Propane Formulas

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Naming

• Straight chain alkanes are named with a base name depending on the number of atoms in the carbon chain and the suffix –ane.

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The most important property of the alkanes is their flammability, the combustion reaction between oxygen and the alkane producing

carbon dioxide and water.

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Saturation

• Alkanes are saturated; they contain the maximum number of hydrogen atoms per carbon atom.

• Alkenes and alkynes are unsaturated. They contain at least one double or triple bond, respectively. They have fewer hydrogen atoms per carbon atom than alkanes.

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Alkenes

• Flammable and nonpolar like alkanes• Double bond makes them more chemically

reactive than alkanes by addition across the double bond

• Bananas exposed to ethene (ethylene) ripen quickly.

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Alkynes• Like alkenes, not commonly encountered

directly• Ethyne (acetylene) is used in welding

torches.

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Isomers• It is possible for organic compounds to

share a molecular formula but have different structures based on the branching of the carbon chain.

• Isomers can differ in their physical and chemical properties.

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Unsaturated Isomers

• Alkenes and alkynes exhibit isomerism based on the position of the multiple bond.

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Naming HydrocarbonsIUPAC Recommendations

Alkanes– Determine the base name of the longest continuous carbon chain.– Consider branches to be substituents of the base chain.– Number the base chain beginning with the end closest to the first

branch.– Order the name:

• Number of the substituent followed by a dash• Name of the substituent • Base name of the compound

– When two or more substituents are present, number each and list them alphabetically.

– Use numbering system that contains the lowest possible numbers.– For two or more substituents on the same carbon, use that

number twice.– Use prefixes to denote identical substituents.

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Naming Alkenes and Alkynes

• Similar to alkanes except for the addition of a number at the beginning to indicate the position of the multiple bond(s)

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Kekule and Aromaticity

• Early structure elucidation– Carbons tendency for 4 bonds

• Dreamed that he saw chains of 6 carbon atoms as snakes– One snake bit its own tail

• Proposed benzene as a ring of 6 carbon atoms

• Structure is still accepted today

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Update on Kekule’s Benzene Ring

• Kekule proposed a ring containing alternating double and single bonds.

• The bonds in benzene have since been found to be all of the same length.

• Each bond is now considered to be midway between a double and a single bond.

• Modern representation is a circle within a hexagon.

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Benzene Structures

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The Benzene Ring

• Particularly stable• When the ring contains substituents it is

called a phenyl ring.• Also called aromatic ring due to the

notable aroma of many compounds containing such a ring

• Two or more fused such rings make polycyclic aromatic hydrocarbons.

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Common Examples

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Functionalized Hydrocarbons• Basic hydrocarbon structures form a foundation for a

major grouping of organic compounds.• Contain additional atoms or groups of atoms• Insertion of functional groups to a hydrocarbon

dramatically alters its properties.

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Representing Functionality

Compounds containing the same functional group are called a family.

Generic symbolism is R-FG where R is the hydrocarbon part of the molecule and FG is the functional group.

R-OH symbolizes the alcohols.

Functional groups help organize and classify organic compounds.

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Chlorinated Hydrocarbons• Found in pesticides, solvents, refrigerant liquids• One or more chlorine atoms substitute for one or

more hydrogen atoms• Lower flammability and reactivity than

hydrocarbons

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DDT

• Muller demonstrated effectiveness against insects and relative non-toxicity to humans.

• Stability made it efficient.• Dramatically decreased malaria in many

countries• Muller awarded Nobel Prize in 1948• Resistance and bioamplification led to

DDT’s ban.

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CFCs

• Chlorofluorocarbons are a subfamily of chlorinated hydrocarbons.

• Chemically stable . . .• Until they reach the high-energy sunlight in

the upper atmosphere• Ozone destruction led to bans.

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Alcohols

• General formula: R-OH• Additional of the –OH makes alcohols

polar.• Increased intermolecular attractive forces

makes alcohols liquids.• Naming involves modifying the

hydrocarbon name with an ending of –ol.

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Ethanol

• Alcoholic beverages• Gasoline additive• Sugar fermentation

• CNS depressant• Adverse health

effects

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Other Alcohols

• Isopropyl alcohol is commonly known as rubbing alcohol.

• Methanol is toxic to the human liver.

• Ethanol is administered as an antidote.

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Aldehydes and Ketones

• Commonly found in pleasant flavors and aromas• Contain the carbonyl group: Carbon double

bonded to an oxygen atom

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Formulas

• Aldehydes– General formula:

RCHO, includes carbonyl group

– Named according to length carbon chain with the ending of –al or –aldehyde

– Methanal or formaldehyde

• Preservation of biological specimens

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Formulas

• Ketones– Similar to aldehydes

but have two R groups with the carbonyl

– Names end in –one– Acetone is the

simplest ketone. • Nail polish removal

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Carboxylic Acids

• Commonly found in sour foods• General formula: RCOOH• One of these oxygen atoms is bonded as

a carbonyl group, as in aldehydes and ketones.

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Esters

• Esters have pleasant odors.• General formula: RCOOR• Named according to the relevant

R groups and ending with –ate

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Ethers• Ethers contain the functional group –

O-• General formula: ROR• Named according to the two R groups

and given the ending ether

• Formerly used as an anesthetic

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Amines• Amines are organic compounds

that contain nitrogen.• General formula: NR3

• Notable for disagreeable odors• Named for R groups present and

ending in –amine

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