Download Chapter 22 - Organic Chemistry Notes

Chapter 25 - Organic Chemistry Notes
Section 1 – Organic Compounds
Organic Compounds - covalently bonded compounds containing carbon (excluding carbonates and oxides).
Carbon-Carbon bonding – carbons are unique b/c they can form long chains and/or rings of bonded atoms.
Catenation is the process of an element bonding to itself to make a chain or ring.
Hydrocarbons – contain hydrogen and carbon chains.
Isomers – compounds with the same molecular formula but different structures.
Structural Formulas: (as shown above) indicate the number and types of atoms AND show the bonding
arrangement.
Condensed Formulas: (as shown below) used for easier reading.
CH3 - O - CH3
CH3 - CH2 – OH
Types of Isomers:
1. Structural Isomers (“Constitutional
Isomers”) – atoms bonded together in a
different order.
2. Geometric Isomers – bonded atoms are in the same order, but appear in different arrangements in 3D
space.
“cis” – odd atoms are on the SAME SIDE
“trans” – odd atoms are on opposite sides
Section 2: Hydrocarbons
Saturated hydrocarbons – each carbon atom forms FOUR single bonds.
Unsaturated hydrocarbons – not all carbon atoms have four single bonds.
Hydrocarbon
Alkane
Description
Contains only
single bonds
General Formula
CnH2n+2
Nomenclature
Ends in –ane
(Saturated)
C3H8
C4H10
Propane
Butane
Alkene
Double bonds
CnH2n
Ends in –ene
Example:
(Unsaturated)
C3H6
C4H8
Propene
Butene
Alkyne
Triple bonds
CnH2n-2
Ends in –yne
Example:
(Unsaturated)
C3H4
C4H6
Propyne
Butyne
Example:
Examples
Propane (above)
Propene (above)
Propyne (above)
Cycloalkanes or cycloalkenes: hydrocarbon in which the chain is connected in a ring…like
Benzene (also known as cyclohexene).
Carbon-Atom Chain Prefixes:
1
2
3
4
5
methethpropbutpent-
6
7
8
9
10
hexheptoctnondec-
Nomenclature for Hydrocarbons:
1. Name parent hydrocarbon chain.
a. Alkane – longest chain of single bonds.
b. Alkene – If you have more than double bond, use suffixes to show how many and where the
double bonds are located, 2=adiene, 3=atriene, 4=tetrene.
c. Alkyne – If you have more than triple bond, use suffixes to show how many and where the
double bonds are located, 2=adiyne, 3=atriyne, 4=tetryne.
2. Add names of the branches
a. If you have one branch, name it.
b. If you have more than one branch of the same kind, use di=2, tri=3, tetra=4.
3. Number the carbons in parent chain.
4. Insert branch position numbers into the name.
5. Punctuate the name.
Examples:
CH3-CH-CH2-CH-CH-CH3
|
|
|
CH3
CH3 CH3
CH3
|
CH3-CH-C=CH2
|
CH2-CH3
Name: 2,3,5-trimethylhexane
Name: 2-ethyl-3-methyl-1-butene
CH3≡≡C-CH-CH3
|
CH3
Name: 2-methyl-1-butyne
Properties & Uses
Alkanes – nonpolar, weak London dispersion forces, as mass increases boiling point also increases, small
molecules are gases, medium molecules are liquids, and large molecules are solids (waxes). Examples:
Gasoline (octane).
Alkenes – nonpolar, similar properties of boiling point and physical state as alkanes, used in commercial
productions like making plastics and plant hormones like ethane (aka ethylene).
Alkynes – nonpolar, same properties as above, used as ethyne (aka acetylene torches) for welding.
Section 3 – Functional Groups
Functional Group – group of atoms that give an organic compound its specific properties.
Name
1. alcohol
2. alkyl halide
3. ether
4.
5.
6.
7.
8.
9.
aldehyde
ketone
amine
carboxylic acid
ester
thiol
Group
Nomenclature
(-OH)
ending in –ol
(-F , -Cl , -Br , -I) use prefix
(-O-)
use ether
use ___ oxy ___
(H-C=O)
ending in –al
(C=O)
ending in –one
(N)
ending in –amine
(-COOH)
ending in –oic acid
(O-C=O)
ending in –oate
(-SH)
ending in –thiol
Example
pentanol
dichloropentane
pentyl ethyl ether
ethoxy pentane
pentanal
pentanone
pentanamine
pentanoic acid
pentanoate
pentane thiol
PRACTICE: Draw the organic molecules for 1-4 and name the molecules for 5-15.
1. 2-pentanol
2. 1-butanol
3. 3-pentanone
4. ethanal
5. CH3-CH2-CH=CH-CH2-CH2-CH3
6. CH3-CH=CH-CH2-CH2-CH3
7. CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3
8. CH3-CH2-CH=CH-CH2-CH2-CH2-CH3
9. CH3-CH3
10.
11.
12.
13.
14. CH3-CH2-CH2-CH2-CH2-CH2-CH2-OH
15.