2003 John Wiley and Sons Publishers

Chapter 6: Introduction to Organic

Chemistry

Courtesy Martyn F.
Chillmaid/Photo
Researchers

The Power of Hydrocarbons

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Courtesy The Granger

Collection

Frederich Wohler synthesized urea in his laboratory in 1828.

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Courtesy Andy Washnik

Organic foods.

Carbon always has 4 bonds

C
single bonds

double bond

triple bond

never quadruple bonds

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Figure 6.2: Methane, CH4.

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Figure 6.3: Methane and the tetrahedral carbon.

 2003 John Wiley and Sons Publishers

Courtesy Tripos Associates

Representation of molecules of methane, CH4, and ethane, CH3 CH3.

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Figure 6.8: Propane

Representing Organic Compounds

Molecular Formula
-- C4H10
Complete structural formula

H H H H
H

H
H

or

H H H H

Condensed structural formula

CH3CH2CH2CH3

Line formula -

CH3
or

or

CH3CHCH3

Isomers - Compounds that have the

same molecular formula but different
structural formulas.

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Isomers of Pentane

Courtesy Michael Pique, The Scripps Research Institute, CA.

Pentane, isopentane, and neopentane.

Isomers of Hexane

Nomenclature alkanes
Find the longest chain of carbon atoms --- this
is the base name of the alkane.
Alkyl groups branch off of the main chain
Main chain is numbered to show where alkyl
groups are attached.

Name this compound

Longest chain highlighted

2 carbon group attached to main

chain

3-ethyl hexane

4-ethyl-2-methyl heptane

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Cycloalkanes

Figure 6.17: Cycloalkanes.

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Courtesy Andy Washnik

Gasoline, mineral oil, lubricating oil and petroleum jelly.

Physiological Properties of Alkanes

Methane (CH4) is physiologically inert.
Cyclopropane (C3H6) is a safe, effective, and fast acting
anesthetic.
Pyrethrins are cyclopropane derivatives found in the pyrethrum
daisy which have insecticidal activity. Pyrethrins are frequently
used in flea sprays.
Liquid alkanes (gasoline) dissolve and wash away oils.
Solid alkanes are applies to the skin as emollients (skin
softeners).

Alkenes double bonds

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Figure 6.13: The carbon-carbon single bond of ethane and the carbon-carbon double
bond of ethylene.

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Figure 6.15: The conversion of unsaturated ethylene to saturated ethane.

Alkynes triple bonds

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Figure 6.18: Three representations of benzene.

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Figure 6.19: Aromatic compounds.

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Figure 6.20: Balanced equations: Each atom of each element among the products
corresponds to an atom of the same element among the reactants.

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Figure 6.21: A burning candle.

QUESTION

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A burning candle releases two different forms

of energy. What are they?

QUESTION

2003 John Wiley and Sons Publishers

In the year 1800 what characteristic was used

to define a chemical as an organic chemical?
What characteristic is used today to define a
chemical as an organic chemical?

QUESTION

2003 John Wiley and Sons Publishers

What is the total number of covalent bonds in

the methane molecule? What is the total
number of electrons in these covalent bonds?
What is the total number of electrons in the
entire methane molecule?

QUESTION

2003 John Wiley and Sons Publishers

Decane is an alkane with 10 carbons in each

molecule. How many hydrogens does each
decane molecule contain?

QUESTION

2003 John Wiley and Sons Publishers

Name three consumer products, found in most

drugstores or supermarkets, that consist
largely or exclusively of alkanes?

QUESTION

2003 John Wiley and Sons Publishers

A pentane molecule contains five carbons, a

decane molecule contains 10 carbons, a
pentadecane molecule contains 15 carbons.
Write the molecular formula of the alkane
octadecane.

QUESTION

2003 John Wiley and Sons Publishers

Draw the molecular structures and give the

IUPAC names of all five isomers of C6H14.

QUESTION

2003 John Wiley and Sons Publishers

The general formula CnH2n+2 can be used to

identify a compound as an alkane. Can the
general formula CnH2n be used similarly to
identify a compound as an alkene?

QUESTION

2003 John Wiley and Sons Publishers

What characteristic of molecular structure is

common to all organic compounds classified
as aromatic?

QUESTION

2003 John Wiley and Sons Publishers

A typical alkane molecule of paraffin wax

contains 25 carbon atoms. Write a balanced
chemical equation for its oxidation to carbon
dioxide and water.