Transcript Document

Organic Compound
Characteristics
9/10/10
• organic compound = a compound composed of these four
elements, hooked together with covalent bonds: carbon, oxygen,
nitrogen, and hydrogen.
• functional group = an atom or group of atoms that is responsible
for the specific properties of an organic compound.
• If an organic molecule has no functional groups, it’s classified as:
• saturated hydrocarbon = a hydrocarbon that contains only
single bonds (therefore, they are alkanes)
• unsaturated hydrocarbon = a hydrocarbon that contains one
or more double or triple bonds (therefore, they are alkenes or
alkynes)
• unsaturated hydrocarbon = a hydrocarbon that contains one or
more double or triple bonds (therefore, they are alkenes or alkynes)
• monounsaturated = one
double/triple bond on the
whole chain
• polyunsaturated = more
than one double/triple bond
on the chain
• Functional groups, once added to the carbon chain, form eight basic
types of organic compounds. Each type of compound has its own
general formula (as was the case with the simple hydrocarbons).
1. alcohols
5. ketones
2. alkyl halides
6. carboxylic acids
3. ethers
7. esters
4. aldehydes
8. amines
1. alcohols = compounds that contain one or more hydroxyl groups.
General Formula:
R―OH
H H
‫׀ ׀‬
H−C−C−OH
‫׀ ׀‬
H H
Note: the O and
the H do have a
bond between
them, but is not
usually shown in
organic structures.
• The structure shown above is ethanol. The hydroxyl group could
have been placed anywhere on the structure.
• Alcohols are used in cosmetic products in the
form of glycerol (a moisturizing agent found in
lotions, lipsticks, antiperspirants, and creams like Noxzema™).
• Alcohols are metabolized into highly toxic products such as
formaldehyde (used to preserve dead bodies) and formic acid (the
“sting” in an ant bite). Ingestion of methanol can lead to optic
nerve damage, coma, and death.
2. alkyl halides = compounds that contain one or more halogen
atoms, that are substituted for a hydrogen atom in a hydrocarbon.
General Formula:
R―X
(X stands for any halogen)
Cl
‫׀‬
Cl−C−F
‫׀‬
F
• The structure shown above is dichlorodifluoromethane. This
chemical is more commonly called Freon-12, and was once used
as a refrigerant, before it was discovered to be a major factor in
ozone depletion.
• Teflon is a widely used
alkyl halide (C2F4) on cookware.
3. ethers = compounds in which two hydrocarbon chains are bonded
to the same atom of oxygen.
General Formula:
R―O―R
H H
H H H
‫׀ ׀‬
‫׀ ׀ ׀‬
H−C−C−O−C−C−C−H
‫׀ ׀‬
‫׀ ׀ ׀‬
H H
H H H
• The structure shown above is ethyl propyl ether.
• Methyl-tertiary-butyl ether (MTBE) is the most widely used ether,
used as a gasoline enhancer. Tetraethyl lead (C2H5Pb) was once
widely used for this purpose, until it was found to be an
environmental contaminant, releasing too much lead into the
environment.
4. aldehydes = compounds in which the carbonyl group is attached to
a carbon atom at the end of a carbon chain.
General Formula:
O

R–C–H
H H O
‫ ׀ ׀‬
H−C−C−C−H
‫׀ ׀‬
H H
• The structure shown above is propanal.
• Methanal (also known as formaldehyde) is the most widely used
aldehyde, used as dead tissue preservative.
• Simple alcohols and formaldehyde can combine
to make certain plastics, such as Bakelite™, one
of the first plastics ever made.
• Some aldehydes are responsible for odors and
flavors. Cinnamaldehyde is responsible for the
odor of cinnamon
(imagine that).
5. ketones = compounds in which the carbonyl group is attached to
the carbon atoms within the carbon chain.
General Formula:
O

R–C–R
H H O H H H
‫ ׀ ׀‬‫׀ ׀ ׀‬
H−C−C−C−C−C−C−H
‫׀ ׀‬
‫׀ ׀ ׀‬
H H
H H H
• The structure shown above is 3-hexanone.
• The simplest ketone is 2-propanone (also known
as acetone). It is the most widely used ketone,
used as a nail-polish remover and degreaser.
• Some ketones are responsible for odors and
flavors. Irone is responsible for the odor of
an iris flower (imagine that).
6. carboxylic acids = compounds which contain the carboxyl group,
attached to a carbon atom at the end of a carbon chain.
General Formula:
O

R–C–OH
H O
‫ ׀‬
H−C−C−OH
‫׀‬
H
• The structure shown above is ethanoic acid (also known
as acetic acid, the main flavoring agent in vinegar).
• A number of carboxylic acids occur in
citrus fruits, such as oranges, lemons,
and limes. Citric acid has a tart flavor,
and sorbic acid can be used as an antibacterial agent, since it kills microorganisms.
• Methanoic and ethanoic acids are the starting materials
for many chemical processes, including the production
of PVA, used in latex paint, adhesives, and textile
coatings like Scotchguard™.
7. esters = compounds which contain the carboxyl group, with the H
from the –OH group removed, and an additional hydrocarbon chain
added.
General Formula:
O

R–C–O–R
H H H O
H H
‫ ׀ ׀ ׀‬
‫׀ ׀‬
H−C−C−C−C−O−C−C−H
‫׀ ׀ ׀‬
‫׀ ׀‬
H H H
H H
• The structure shown above is
ethyl butanoate. This compound
is responsible for the odor of
pineapple.
• Esters are also responsible for fruit ripening. Grocery stores spray
esters on unripened fruit in order to get them to ripen in the store.
+ ester 
8. amines = compounds which can be considered derivatives of
ammonia, NH3.
General Formula:
R–N–R’
|
R”
• Amines are found in a variety of neurotoxins,
produced by poisonous animals. Batrachotoxin
interferes with proper nerve cell functioning, so a
continuous firing happens, resulting in cell death.
• Others are responsible for odors, like putricine and
cadaverine, along with skatole (feces) and
methylamine (dead fish).
• Still others are known as alkaloids, and
include compounds that have physiological
effects, such as caffeine, nicotine, and
morphine.