Bettelheim / Brown / Campbell / Farrell / Torres

Introduction to General, Organic, and Biochemistry 11e

Chapter 10
Organic Chemistry

William H. Brown Beloit College www.cengage.com/chemistry/bettelheim

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Organic Chemistry
Organic chemistry: The study of the compounds of
carbon.
• Organic compounds are made up of carbon and only a
few other elements.
• Chief among these are hydrogen, oxygen, and
nitrogen.
• Also present in some organic compounds are sulfur,
phosphorus, and a halogen (fluorine, chlorine,
bromine, or iodine).

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Organic Chemistry
Why is organic chemistry a separate discipline within
chemistry?

Historical: Scientists at one time believed that a “vital

force” present in living organisms was necessary to
produce an organic compound.
• The experiment of Wöhler in 1828 was the first in a
series of experiments that led to the demise of the vital
force theory.

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 Organic Chemistry
The sheer number of organic compounds
• Chemists have discovered or made over 10 million
organic compounds and an estimated 100,000 new
ones are discovered or made each year.
• By comparison, chemists have discovered or made an
estimated 1.7 million inorganic compounds.
• Thus, approximately 85% of all known compounds are
organic.
The link to biochemistry
• Carbohydrates, lipids, proteins, enzymes, nucleic
acids, hormones, vitamins, and almost all other
chemicals in living systems are organic compounds.

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Organic Chemistry
A comparison of organic and inorganic compounds

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Organic Structure
Structural formula: Shows the atoms present in a
molecule and the bonds that connect them.
VSEPR model: The most common bond angles are
109.5°, 120°, and 180°.

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Organic Structure
Among neutral (uncharged) organic compounds:
• Carbon normally forms four covalent bonds and has no
unshared pairs of electrons.
• Hydrogen forms one covalent bond and no unshared
pairs of electrons.
• Nitrogen normally forms three covalent bonds and has
one unshared pair of electrons.
• Oxygen normally forms two covalent bonds and has
two unshared pairs of electrons.
• Halogen normally forms one covalent bond and has
three unshared pairs of electrons.

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Functional Groups
Functional group: An atom or group of atoms within a
molecule that shows a characteristic set of predictable
physical and chemical properties.
Functional groups are important because
• They undergo the same types of chemical reactions no
matter in what organic molecule they are found.
• To a large measure, they determine the chemical and
physical properties of a molecule.
• They are the units by which we divide organic
compounds into families.
• They provide the basis on which we derive names for
organic compounds.

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Functional Groups

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Alcohols
Alcohol: Contains an —OH (hydroxyl) group bonded to a
tetrahedral carbon atom. For example, ethanol:

• Alcohols are classified as primary (1°), secondary

(2°), or tertiary (3°).

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Alcohols
Problem: Draw Lewis structures and condensed structural
formulas for the two alcohols with the molecular formula
C3H8O.

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Alcohols
Problem: Draw Lewis structures and condensed structural
formulas for the two alcohols with the molecular formula
C3H8O.
Solution:

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Amines
Amine: A compound containing an amino group (-NH2,
RNH2, R2NH, R3N).
• Amino groups are classified as primary (1°),
secondary (2°), or tertiary (3°).

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Amines
Problem: Draw condensed structural formulas for the two
primary amines with the molecular formula C3H9N.

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Amines
Problem: Draw condensed structural formulas for the
two primary amines with the molecular formula C3H9N.
Solution:

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Aldehydes and Ketones
Each contains a C=O (carbonyl) group.
• Aldehyde: Contains a carbonyl group bonded to a
hydrogen; in formaldehyde, the simplest aldehyde, the
carbonyl group is bonded to two hydrogens.
• Ketone: Contains a carbonyl group bonded to two
carbon atoms.

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Aldehydes and Ketones
Problem: Draw condensed structural formulas for the two
aldehydes with the molecular formula C4H8O.

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Aldehydes and Ketones
Problem: Draw condensed structural formulas for the two
aldehydes with the molecular formula C4H8O.
Solution:
• First draw the functional group of an aldehyde and add
the remaining three carbons; these may be bonded in two
ways.
• Then add the seven hydrogens necessary to complete the
four bonds of each carbon.

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Carboxylic Acids
Carboxylic acid: A compound containing a -COOH
(carboxyl: carbonyl + hydroxyl) group.
• In a condensed structural formula, a carboxyl group may
also be written -CO2H.

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Carboxylic Acids
Problem: Draw a condensed structural formula for the
single carboxylic acid with the molecular formula C3H6O2.

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Carboxylic Acids
Problem: Draw a condensed structural formula for the
single carboxylic acid with the molecular formula C3H6O2
Solution: The only way the carbon atoms can be written is
three in a chain; the -COOH group must be on an end
carbon of the chain.

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Carboxylic Acids
Problem: Draw a condensed structural formula for the
single carboxylic acid with the molecular formula C3H6O2
Solution: The only way the carbon atoms can be written is
three in a chain; the -COOH group must be on an end
carbon of the chain.

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Carboxylic Ester
Carboxylic ester: A derivative of a carboxylic acid in
which the H of the carboxyl group is replaced by a carbon
group.

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Carboxylic Amide
Amide: A derivative of a carboxylic acid in which the —OH
of the carboxyl group is replaced by an amino group.

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