The Hydrocarbons: Part 3, Alkenes PharmChem 2019:

Introduction and Nomenclature:

Isomerism – geometric isomerism

Essential Organic Chemistry, Paula Bruice

Alkenes in nature
The visual systems of all organisms is based on cis-retinal
Alkenes
- contain at least one C=C double bond, they are unsaturated compounds
- Also known as olefins
- The general molecular formula (acyclic) CnH2n
- The double bond is the functional group in alkenes

Nomenclature of alkenes
- replace the ane at the end of the parent hydrocarbon’s name with suffix ene
1. Find LCCC that includes the double bond and
2. Number chain in direction that gives lowest number to doubly bonded carbon.
2. For a compound with 2 double bonds, the “ne” ending of corresponding
alkane is replaced with “diene”.

hepta-2,4-diene 2,4-heptadiene

3. If a substituent is present, identify its position by a number. The functional

group suffix gets the lowest possible number.

4-methylpent-2-ene
4. If more than one substituent, list alphabetically and assign substituents
appropriate position numbers

6-ethyl-3-methyloct-3-ene

5. If counting in both directions gives the alkene the same number, then the
correct name contains the lowest substituent number.

2,5-dimethyloct-4-ene
Examples of naming rules – self study
Examples of naming rules – self study

Rule 5
Constitutional isomers are possible for alkenes but in addition, alkenes have
a double bond (a ……. and a ….. bond) thus, stereoisomers arise.

restricted rotation - groups on one side cannot rotate to the other side
Cis and Isomers

- Only possible if 2 substituents on each of the sp2 carbons are different