Organic Chemistry
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Organic Compounds
Organic compounds are molecules that
contain carbon.
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Carbon is the base of organic compounds for 3
reasons:
1.
Carbon forms stronger covalent bonds than most other
non-metals
2.
Carbon forms more stable molecules than most other
non-metals
3.
Carbon can form up to 4 bonds at a time, which gives
many possibilities for molecules.
Structure of Organic Compounds
Besides carbon, the most common elements in
organic compounds are: H, O, N, S, & halogens.
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Organic compounds are held together with covalent
bonds.
Organic compounds must meet the octet rule (S does
not break the octet rule)
Hydrocarbons
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Hydrocarbons are the most simple organic compounds
•
Hydrocarbons only contain C & H
•
All other organic compounds are derivatives of hydrocarbons
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Petrochemicals contain hydrocarbons, including: propane,
butane, and octane
Saturated – a compound is termed “saturated” if it has the
maximum hybridization (sp3) at each carbon!
Therefore: no double or triple bonds
Hydrocarbons
C2H6
Alkanes
• Single
bonded
carbons
C6H12
C2H2
Alkynes cycloalkane
• A triple
• ring
bonded
carbon
C2H4
Alkenes
A double
bonded
carbon
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•
CnH2n
Strongest, • Weaker, less • Weakest,
stable
least stable
most stable
hydrocarbons hydrocarbo hydrocarbons
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ns
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CnH2n+2
saturated
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CnH2n
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unsaturated
CnH2n-2
unsaturated
•
unsaturated
C6H6
Aromatics
Ring of
carbons
with
alternating
double
and single
bonds
Simple Organic Nomenclature
Prefixes used with organic compounds
1. meth6. hex2. eth7. hept3. prop8. oct4. but9. non5. pent10. dec-
Suffixes used with
organic
compounds
-ane = CnH2n+2
-ene = CnH2n
-yne = CnH2n-2
Name the following organic compounds
a. CH4
b. C3H8
c. C3H6
d. C4H10
e. C5H8
f. C3H4
methane
___________________
propane
___________________
propene
___________________
butane
___________________
pentyne
___________________
propyne
___________________
Nomenclature Rules
Procedure for naming carbon chains containing branches or
substituents (non-straight chain)
1) Find the longest continuous carbon chain in the structure-this
determines the root name
2) Any carbon not on this continuous chain is a substituent (appendage)
3) Number the main chain starting from the end closest to the first
substituent
4) The substituents are still named according to the number of carbons
(the suffix for a substituent is –yl instead of –ane)
-CH3 methyl
-CH2CH3 ethyl
5) Place all substituent names before the root name in alphabetical order
6) The substituent must be numbered to indicate the point of attachment
to the main chain
7) Group multiple substituents of the same kind together and label di-, tri, etc.
8) When alphabetizing, the prefixes di-, tri- are ignored
9) With a ring compound the number of carbons in the ring determines
the root name with a cyclo- prefix
10) Halogens are named as substituents with an -o suffix
e.g. fluoro-, chloro-, bromo- or iodo-
Isomers - Compounds with the same molecular
formula but different structural arrangement
therefore a different name.
C6H14
A.
B.
C.
D.
hexane
2-methylpentane
3-methylpentane
2, 2-dimethylbutane
E. 2,3-dimethylbutane
Draw & Name the following
1-Butene
H
H
H
C
C
C
H
H
H
H
H
H
C
C
C
H
H
H
H
C
C4H8
H
3-Heptyne H
C7H12
H
H
C
C
H
H
C
C
H
C3H6 or CH3CH=CH2
H
H
H
1-propene
H
C
C
C
H
H
C4H8 or H2C=CHCH2CH3
1-Butene
H
C
H
H
H
C
C
C
H
H
H
H
Functional Groups
Functional groups are any atom, group of
atoms, or organization of bonds that determine
the properties of a molecule.
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Functional groups are the most reactive part of a
molecule
Functional groups directly determine the properties of
a molecule
Functional Groups
a. Alcohols: -OH
Add –ol to name
When carbon is single bounded to an –OH
Ex. Propanol
H
3-pentanol
••
O
••
H
H
H
C
C
C
H
H
H
H
b. Aldehydes: -C=OH - always on the end
Example:
Add –al to name
pentanal
c. Carboxylic Acids: COOH
Most common organic acids belong to this group.
Add –oic Acid to name
Example:
Propanoic Acid
d. Ketones: -C=O (also called a carbonyl group)
Example:
Add –one to name
4 -octanone
e. Esters are formed when a carboxylic acid reacts
with an alcohol. This reaction is called
esterification.
Add –oate to name
–O-C=O
Example:
methyl butanoate
Smells like pineapple
f. Halohydrocarbons: Halogen substituted for
a hydrogen
Example:
2-bromo-2-chloro-1,1,1-trifluoroethane.
••
•• F
••
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•
••••
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F • •Br•
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C
C
•• F •• ••Cl ••
•• ••
H
Polymers
Polymers are long carbon chains made of
repeating units
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Both natural and synthetic (man-made)
Natural Polymer Examples
•Nucleic
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Acids
Examples: DNA, RNA
Carbohydrates
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Examples: starches, sugars
•
Example: lactase
• Enzymes (protein catalysts that speed up chemical
reactions)
Vitamins (naturally in plants & animals)
• Insulin (naturally made in your body)
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Synthetic Polymer Examples
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Plastics (made from
petrochemicals)
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Examples: polystyrene,
Styrofoam, polyvinyl chloride
(PVC), nylon
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Kevlar (used in ballistic
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Pharmaceuticals
vests and combat helmets)
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First synthetic pharmaceutical
was aspirin