Organic Language

©Rohen Prinsloo, Department of Chemistry, University of Calgary 1

How to Draw Organic Molecules
Rules For Line Notation
1. The end of any line indicates a carbon atom, unless another atom is
indicated.
2. Any place where two or more lines meet represents a carbon atom,
unless another atom is indicated.
3. Multiple bonds are clearly indicated
4. Assume any missing valencies are filled by hydrogens.
5. All non-carbon atoms (heteroatoms) are clearly indicated.
6. Unshared pairs are implied, but not always shown.

A “heteroatom” is any atom different from carbon or hydrogen.

“hetero” = different (Greek)
©Rohen Prinsloo, Department of Chemistry, University of Calgary 2
How to Draw Organic Molecules
Examples:

CH3CH2CH2CH2CH3

©Rohen Prinsloo, Department of Chemistry, University of Calgary 3

Naming Organic Molecules

©Rohen Prinsloo, Department of Chemistry, University of Calgary 4

Hydrocarbons as building blocks
▪ Alkanes as a functional group
In general, alkanes are not considered as a functional group - the C-C and C-H
bonds are too unreactive. However, technically, the C-H and C-C bonds in
alkanes are the functional groups.

▪ Hydrocarbons are used as scaffolds to which all other functional groups can be
attached

Tylenol Advil

©Rohen Prinsloo, Department of Chemistry, University of Calgary 5

Naming alkanes
The number of constitutional isomers increases rapidly as we
increase the carbon number

©Rohen Prinsloo, Department of Chemistry, University of Calgary 6

Naming alkanes

methane CH4 CH4

ethane CH3CH3 C2H6
propane
CH3CH2CH3 C3H8
n-butane
CH3CH2CH2CH3 n-C4H10
n-pentane
CH3CH2CH2CH2CH3 n-C5H12
n-hexane CH3(CH2)4CH3 n-C6H14
n-heptane CH3(CH2)5CH3 n-C7H16
n-octane CH3(CH2)6CH3 n-C8H18
n-nonane CH3(CH2)7CH3 n-C9H20
n-decane CH3(CH2)8CH3 n-C10H22

“n” means normal

©Rohen Prinsloo, Department of Chemistry, University of Calgary 7
 Hydrocarbons and Substituents

▪ When replacing a H atom of the parent hydrocarbon, we form an alkyl substituent.

▪ Substituents and functional groups are the building blocks of organic compounds
▪ They form the foundation of organic nomenclature.

©Rohen Prinsloo, Department of Chemistry, University of Calgary 8

Common Hydrocarbon Substituents

Aryl groups (Ar)

©Rohen Prinsloo, Department of Chemistry, University of Calgary 9
Alkyl groups (R)
Common Hydrocarbon Substituents

©Rohen Prinsloo, Department of Chemistry, University of Calgary 10

Organizing Organic Compounds

Organic chemistry can be organized according to the functional

groups.

Functional groups are specific groups of atoms within a molecule

that are responsible for the characteristic chemical reactions of the
molecule.

Why do we organize organic chemistry around functional groups?

▪ Because the chemical reactivities of the same functional group
in different molecules are similar.
▪ Functional groups in a molecule are usually the most reactive
sites

©Rohen Prinsloo, Department of Chemistry, University of Calgary 11

Common Functional Groups

alcohol 1° amine 2° amine 3° amine

epoxide ether nitrile nitro group

thiol sulfide carbonyl aldehyde

ketone carboxylic ester amide

acid
©Rohen Prinsloo, Department of Chemistry, University of Calgary 12
IUPAC nomenclature of Organic Molecules
▪ n-Hexane has 5 constitutional isomers, how do we identify each isomer?

▪ The solution is a systematic nomenclature system following the IUPAC RULES.

I nternational
pronounced as: “eye-you-pac”
U nion of
P ure and Developed between 1946-1950 and still evolving
A pplied
C hemistry
▪ It is a system where every compound (even isomers) has a unique name.

▪ Once given the name, anyone can draw the structure of the compound.

LEARN ORGANIC NOMENCLATURE ON YOUR OWN

http://www.chem.ucalgary.ca/courses/351/WebContent/orgnom/index.html
©Rohen Prinsloo, Department of Chemistry, University of Calgary 13
IUPAC nomenclature of Organic Molecules
The name of every compound has 3 fields:
1. The 1st field indicates the name and positions of the substituents
2. The 2nd field contains the compound root word
3. The 3th field defines the principal functional group.

1st 2nd 3th

Substituents Compound Principal
+ root + functional group
2,4-Dimethyl pent ane
4-Ethyl-3-methyl heptan 3-ol

IUPAC 2,4-Dimethyl-pentane 4-Ethyl-3-methyl-heptan-3-ol

©Rohen Prinsloo, Department of Chemistry, University of Calgary 14

Examples of Functional Groups

Alkenes (contain C=C, double bond) Alkynes (contain C≡C, triple bond)

Limonene Calicheamicin
Alcohol (contain hydroxide group) Alkyl halide (contains fluoro,
chloro, bromo, iodo)

sucrose Polyvinyl chloride

©Rohen Prinsloo, Department of Chemistry, University of Calgary 15
Examples of Functional Groups

Amine (contains amino group) Epoxide (contains an oxygen in a

three membered ring with 2 carbons)

MDEA Epichlorohydrin

Ether (contain alkoxy group, -O-R) Nitrile (contains cyano group)

Diethyl ether acrylonitrile

©Rohen Prinsloo, Department of Chemistry, University of Calgary 16
 Examples of Functional Groups

Nitro (contains a nitro group) Thiols (contains a thiol group)

Trinitrotoluene, “TNT” “Skunk smell”

Thioethers (contains a sulfide group)

“Truffles” smell
©Rohen Prinsloo, Department of Chemistry, University of Calgary 17
Examples of Functional Groups

Carbonyl compounds Aldehyde (contains carbonyl group

joined to a hydrogen atom)

2-methylundecanal
Carbonyl group
“Chanel No 5”
Ketone (contains carbonyl group Carboxylic Acid (contains
joined to two carbon atoms) carboxyl group)

“Raspberry ketone” Citric acid

©Rohen Prinsloo, Department of Chemistry, University of Calgary 18
Examples of Functional Groups

Esters (contains a carboxyl group Amide (contains amide group)

connect to an alkyl group)

“Banana like smell” paracetamol

Carboxylic acid derivative

Acid anhydride
©Rohen Prinsloo, Department of Chemistry, University of Calgary 19