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 Description General Formula Nomenclature Examples
Alkane Contains only CnH2n+2 Ends in –ane
single bonds

(Saturated) C3H8 Propane

Example: C4H10 Butane
Propane (above)
Alkene Double bonds CnH2n Ends in –ene

Example: (Unsaturated) C3H6 Propene

C4H8 Butene
Propene (above)
Alkyne Triple bonds CnH2n-2 Ends in –yne

Example: (Unsaturated) C3H4 Propyne

C4H6 Butyne
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 meth- 6 hex-
2 eth- 7 hept-
3 prop- 8 oct-
4 but- 9 non-
5 pent- 10 dec-

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 Name: 2,3,5-trimethylhexane
| | |
CH3 CH3 CH3

CH3
|
CH3-CH-C=CH2 Name: 2-ethyl-3-methyl-1-butene
|
CH2-CH3

CH3≡≡C-CH-CH3 Name: 2-methyl-1-butyne

|
CH3

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 Group Nomenclature Example

1. alcohol (-OH) ending in –ol pentanol
2. alkyl halide (-F , -Cl , -Br , -I) use prefix dichloropentane
3. ether (-O-) use ether pentyl ethyl ether
use ___ oxy ___ ethoxy pentane
4. aldehyde (H-C=O) ending in –al pentanal
5. ketone (C=O) ending in –one pentanone
6. amine (N) ending in –amine pentanamine
7. carboxylic acid (-COOH) ending in –oic acid pentanoic acid
8. ester (O-C=O) ending in –oate pentanoate
9. thiol (-SH) ending in –thiol 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.