Unit 17: Organic Chemistry

Name given to the study of carbon and carbon compounds.

Living things contain many organic compounds. Products of living things, such as
petroleum, wood and coal supply the raw materials from which organic chemicals are
obtained.
I.
Characteristics of Organic Compounds
A. Organic compounds are generally
nonpolar in nature. (symmetrical charge
distribution)
B. Only a few are
soluble
water.
in
(These include ethanoic acid,
various sugars and some alcohols)
C. Organic compounds are generally
and as a result are
nonelectrolytes; they do not ionize well
poor conductors of electricity.
D. Due to weak intermolecular forces of attractions, organic compounds usually have
low melting points.
E. Reaction rates of organic compounds tend to be
slower
than those of
inorganic compounds. The bonding within the organic molecules itself
covalent
and very
hybridization
of these
(intramolecular as opposed to intermolecular forces) are
strongly held together.
II.
Bonding:
A. Carbon has
4
valence electrons. Due to the
valence sublevels, carbon has
structure.
4
sites for bonds, forming a
tetrahedral
B. Structural formulas are often used to represent the molecule:
Ex: Methane
CH4
C. Isomers: compounds with the same molecular formula, but
different
structures, so different properties
Ex: C5H12
D. Carbon can bond with a second carbon by sharing
III.
__1_____ pair(s) of electrons
(single
bond)
___2_____ pair(s) of electrons
(double
bond)
___3_____ pair(s) of electrons
(triple
bond)
Hydrocarbons: organic compounds containing only
A. Homologous Series:
H and C
a group of organic compounds with similar properties
and related structures (each successive number
increases by 1 carbon and 2 hydrogens)
Table Q
Alkanes: CnH2n+2
Alkenes:
CnH2n
Alkynes:
CnH2n-2
Benzenes:
CnH2n-6
1. To name these compounds, you use prefixes dependents upon the number
of carbons present in the substance. TABLE P
B. Aliphatic Compounds (Compounds that are aligned in a
straight
chain)
1. Alkanes: CnH2n+2
All C to C bonds are
single
. This compound is said to be
saturated -has the max # of H around each C
possible
To name alkanes: Use the prefix + -ane
# of carbons
name
molecular formula
1
methane
CH4
2
ethane
structural formula
3
4
2. Alkenes: CnH2n
Hydrocarbons containing one
double
carbon to carbon bond.
Because of the double bond they are said to be
unsaturated
(they have less hydrogen atoms than do saturated compounds with the
same number of carbons) *Cannot have a 1 carbon alkene*
To name alkenes: use prefix + -ene
# of carbons
name
molecular formula
structural formula
1
*cannot have – you need 2 carbons for the double bond
2
ethene
C2H4
3
4

If the double bond is not on an end carbon, the name of the alkene will
change as follows:
Number the carbons from the end of each side…then
use the smallest number to tell where the double bond
is located.
3. Alkynes: CnH2n-2
.unsaturated
hydrocarbons with one
triple carbon to carbon bond.
To name alkynes: use the prefix + -yne
# of carbons
name
1
*cannot have – you need 2 carbons for the triple bond
2
ethyne
3
molecular formula
structural formula
4

If the triple bond is not on an end carbon, the name of the alkyne will change
as follows:
Number the carbons from the end of each side…then use the smallest number to
tell where the triple bond is located.
C. Aromatic Hydrocarbons: closed chain (ring chain) structures that are often
unsaturated with alternating double and single bonds.
1. The Benzene Family: CnH2n-6
*you should know the following two*
a. Benzene: C6H6
b. Toluene: C7H8
IV.
Functional Groups: an atom (ion) or group of atoms polyatomic ion) responsible
for
specific properties and characteristics of organic
compounds
V.
Table R
Other Organic Compounds:
A. Organic Alcohols: General Formula
R-OH
1.Monohydroxyl alcohol:
a. contains
one
-OH group(s)
b. to name: use alkane name, drop the e and add –ol
c. most alcohols are monohydroxyl
Example:
Structure
1a. Primary Alcohol:
Molecular Formula
Name
one with the –OH group attached to an end carbon
(attached to a carbon that is attached to only one
other carbon)
ex:
1b. Secondary Alcohol:
one with the –OH group attached to a carbon that is
attached to two other carbons
ex:
To name a secondary alcohol, you must name the longest carbon chain and everything that
is attached to that chain is named as you would name the alkenes and alkynes.
Ex:
one with the –Oh group attached to a carbon that is
1c. Tertiary Alcohol:
attached to three other carbons.
Ex:
*name the same way you would name secondary alcohols!
2. Dihydroxyl Alcohols:
a. contains
two
-OH group(s)
b. to name: use alkane name, drop the e and add –diol *also include the
carbon #’s the –OH groups are attached to.
c. you should know:
Structure
C2H4(OH)2
Stock Name
Common Name
3. Trihydroxyl Alcohols
a. contains
three
-OH group(s)
b. to name: use alkane name, drop the e and add –triol *also, name the
carbon #’s the –OH groups are attached to.
c. you should know:
Structure
C3H5(OH)3
Stock Name
Common Name
B. Organic Acids (Carboxylic Acids) *weak electrolytes*

The only organic electrolytes
1. General Formula:
R-COOH or R-C-O-H
a. to name: use alkane name, drop the e and add –oic acid
Molecular Formula
Structure
Name
1
2
C. Aldehydes:
1. General Formula
R-CHO or R-C-H
a. to name: use the alkane name, drop the e and add -al
Molecular Formula
Structure
1
2
**be careful, name is close to alcohol name!!!
Name
D. Ketones:
1. General Formula
R-C-R
a. to name: use the alkane name, drop the e and add –one, also
name the # of the carbon containing the =O
Molecular Formula
Structure
Name
E. Esters: The product of a combination reaction between an acid and an alcohol.
1. General Formula
R-COOR’ or R-C-O-R’
a. to name: use the beginning of the alcohol name and the ending of
the acid name. Change the acid name by dropping –ic and adding
–ate.
Molecular Formula
Structure
Name
F. Ethers:
1. General Formula
R-O-R’
a. to name: name the groups attached to the –OMolecular Formula
Structure
Name
*Diethyl ether is commonly used as a solvent and anesthetic*
G. Halides: alkanes with halogens attached, either by addition or substitution
reactions.
1. General Formula
R-X where X is any halogen
a. to name: use the carbon # the halogen is attached to, then the
prefix of the halogen, then the alkane (or alkene) name.
Halogen Prefixes:
Molecular Formula
F
fluoro
Cl
chloro
Br
bromo
I
iodo
Structure
Name
H. Amines:
1. General Formula
R-NH2; functional group –NH2
a. to name: drop the e off the alkane name, add -amine
Molecular Formula
Structure
Name
I. Amino Acids: the building blocks of proteins, they are the combination of acids
and amines.
1. Simple amino acids are named using the IUPAC system, but most are
complex and common names are used.
Example:
J. Amides: the combination of an amine and an aldehyde
1. General Formula
R-C-NH2
a. to name: drop the e from the alkane name and add -amide
Molecular Formula
VI.
Structure
Name
Organic Reactions:

Generally very slow in nature

Usually only the functional group is involved
A. Substitution Reactions: only saturated hydrocarbons undergo substitution
reactions.
Process by which
an H on an alkane is replaced by
another substance (usually a halogen)
Start with 2 reactants
(alkane + something)
Example:
end with 2 products
B. Addition Reactions: only unsaturated hydrocarbons undergo addition
reactions.
Process by which
an alkene or alkyne react with
something (such as a halogen) to break the
double or triple bond and add a substance on.
Start with 2 reactants
end with 1 product
(alkene/alkyne + something)
Example:
Remember how to name the products of substitution and addition reactions, these are
your Halides.
Examples:
C. Fermentation:
Process by which
enzymes (usually produced in
living organisms) catalyze the breakdown of
large organic molecules to produce alcohol and
CO2.
*usually yeast is involved, the enzymes produced by these yeasts act as
a catalyst for the breakdown of organic molecules.
Example:
.
D. Esterification:
Process by which
an organic acid and alcohol react to
produce an ester and H2O
*dehydration synthesis
*condensation reactions
Organic acid
+
alcohol
=
ester
+
water
E. Saponification:
Process by which
fats are hydrolyzed by strong
bases to produce soap and glycerol
Example:
F. Polymerization:
Process by which
a larger molecule (polymer) is
made from smaller, repeating units.
Polymer:
a compound with a high molecular
mass made up of smaller subunits (monomers)
that have been bonded together.
Types of polymers:
Natural: proteins, starch, cellulose
Synthetic: polyester, polyurethane, plastics, rubber, nylon,
styrofoam
General Reaction:
nC2H4 = (-C2H4-)n
Types of Polymerization Reactions:
1. Condensation polymerization:
2. Addition polymerization:
releases water
breaks double or triple
bonds
G. Oxidation by Aldehydes:
Process by which
an aldehyde reacts with oxygen to
produce an acid
Example:
H. Combustion:
Process by which
saturated hydrocarbons react with
oxygen (are burned) to produce carbon dioxide,
water and heat.
*usually considered the burning of fossil fuels