Organic Nomenclature

How do you know what to call

All of those living chemicals?
 Four Major Classes of Hydrocarbons

Alkanes contain C C single bonds

Alkenes - contain C=C double bonds

Alkynes contain C = C triple bonds

Aromatics contain benzene

Naming Branched- Chain Alkanes
1 2 3 4 5 6
1 2 3 4 5
3,5-dimethylheptane

3-ethyl-5-methylheptane

2,3,3,7,8-pentamethyldecane
Now name it!
1 2 3 4 5 6 7
3,5,5-trimethylheptane

C C

C
5 4 3 2 1

4 3 2 1

5 4 3 2 1
Name them:

CH3-CH2-CH=CH-CH3
2-pentene
H HHH H
H-C-C-C=C-C-H
H H H

C-C-C=C-C
Pentene, but you cant know where the
C5H10
double bond is.
Alkenes:

Have at least one double bond.

The general formula for alkenes with ONE double bond is

Cn H2n

Because of the double bond, in addition to the structural

isomer where the alkene with different placement of
branched chains and the double bond, you can also have
Stereoisomers, geometric isomers.

Stereosiomers have the same molecular formulas and the

same atom-to-atom bonding sequences, but the atoms differ
in their arrangement in space.
Example
Another possible isomer

But not a stereoisomer.why?

They are different
Chemicals and behave
Differently.
Or Stereoisomers
Cyclic Hydrocarbons
- compounds with C and H that form rings

Cycloalkanes

Cyclopentane
Cyclobutane

?
Cyclopropane Cyclohexane
 PQ

Matching

A._____R-OH 1. Carboxylic Acid

B._____R-NH2 2. Ester
O
C._____ 3. Alcohol
R C OH
O
D._____ 4. Amine
R C OR'
Alcohols
R= H
H
R = -CH3
R C OH Primary Alcohol R = -CH2 CH3
H

H
R = -CH3
R C OH Secondary Alcohol
R = -CH2 CH3
R'

R"

R C OH Tertiary Alcohol R = -CH3

R = -CH2CH3
R'
Naming Compounds with Functional Groups

1. Name the longest Chain, including the

functional group.

2. Number Cs from the end closest to the

functional group.

3. Apply the appropriate ending to the

chains name.

4. Give the address of the functional group

and any other groups attached to the
main chain.
 Alcohols

R'
R, R, R can be
R C OH
H, -CH2 ,-CH2 CH3, ..
R"

If R = -CH3 ; R = -CH2CH3 ; R = -CH2CH2CH3

2 1
CH2CH3 hexane
3
CH3 C OH 3-methyl- 3- hexanol

CH2CH2CH3
4 5 6
Aldehydes

R C H al ending
Carboxylic Acids

O
oic acid ending
R C OH
Ketones

O
one ending
R C R'

O
||
CH3 CH2 C CH3 buta-2-none
Amines
Carbon chain name and the amine ending

R-NH2 Where R is CH3 , this becomes Methanamine.

If R is CH3CH2CH2 , this becomes Propanamine

What would CH3 CH2 CH2 CH2 CH2 NH3 be?

How about CH3 CH CH3 ??

|
NH3
Ethers
The shorter of the two chains (R-O-R)
R-O-R becomes the first part of the name with the
-ane suffix changed to -oxy, and the longer
alkane chain become the suffix of the name
of the ether. Thus.

If: R=R= CH3

CH3 O- Methoxy Methane
CH3
If: R= -CH2 CH3 R = -CH2-CH2-
CH3 CH CH O - CH -CH - Ethoxy Propane
3 2 2 2
CH3
 Ethanol as a beverage

Ethanol is produced for beverages by fermentation

Carbohydrates from a wide variety of plant sources

By fermentation alcohol content can get to 12% befo

the fermentation stops due to alcohol inhibiting yeas
action

To get higher concentrations of alcohol this is done b

Distillationethanol distilling before water.

Proof = 2x s the percentage of alcohol

40% alcohol is 80 Proof

Carboxylic Acids

Weak acids (proton donors)

Formed by the oxidation of Alcohols or Aldehydes

H H Ox O
R C
Ox
OH R C O
R C OH
H
Aldehyde
Alcohol Carboxylic
Acid
 A number of carboxylic acids are found in nature.

Ethanoic Acid (Acetic acid) is produced at about 5% in

vinegar

Carboxylic acids with two acid groups are used to pro

Many of the polymers that we enjoy.

Most of these are generally known as polyesters.

 O
Esters
R C O-R
OH

O O

CH
R3 C OH + H-O-CH - CH CH
R3 C O-CH
OH 2-
2 3

Ethanol CH3
Ethyl Ethanoate
Ethanoic Acid

1. Name the Carbon Chain of the Alcohol as an alkyl

2. Change the Name of the Acid by dropping the ic
and add ate
 Esters

Esters typically have very pleasant odors and flavors

The characteristic aromas and tastes of fruits and flow

Are due to natural esters.
Hydrogen bonding in alcohols greatly influences some
Of their physical properties.

e.g. boiling point is higher than expected

Alcohols are very soluble in water; however

as the carbon chain gets longer the solubilit
becomes less.
More than 1 alcohol group can be present in a
single molecule

1,2-Ethanediol (Ethylene Glycol) a di-alcohol is used

as anti-freeze

1,2,3-Propanetriol (Glycerol) - a tri-alcohol that holds

moisture ; it is used in
food, tobacco, cosmetics,
etc.
 Some Common Names to Know

IUPAC Name Common Name

Methanoic Acid Formic Acid

Methanal Formaldehyde
Ethanoic Acid Acetic Acid
Methanol Methyl Alcohol
Ethanol Ethyl Alcohol

Ethene Ethylene