Sign In

7.4 : Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.

An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not interconvertible at room temperature because of the restricted rotation of the double bond.

Figure1left Figure1right
cis-2-Butene trans-2-Butene

For tri- or tetrasubstituted compounds, the E,Z nomenclature has been adopted over the cis and trans nomenclature. The E,Z nomenclature is based on the sequence rules. The carbon atoms across the double bond are envisioned separately, and the substituent with connecting atoms having higher atomic numbers is assigned the highest priority. If two substituents have the same atomic number, the first point of difference is decisive. When the high-priority substituents on both the carbon atoms of the double bond are on the same side, the alkene has a Z configuration, whereas when the high-priority substituents are on the opposite side of the double bond, the alkene is said to have an E configuration.

Figure2left Figure2right
Z Configuration E Configuration
Tags
IsomerismAlkenesConstitutional IsomerismPosition Of Double BondStereoisomerismSpatial ArrangementCis 2 buteneTrans 2 buteneInterconvertibleRestricted RotationEZ NomenclatureSequence RulesAtomic NumbersHighest PriorityZ ConfigurationE Configuration

From Chapter 7:

article

Now Playing

7.4 : Isomerism in Alkenes

Alkene Structure and Reactivity

10.0K Views

article

7.1 : Structure and Bonding of Alkenes

Alkene Structure and Reactivity

12.6K Views

article

7.2 : Nomenclature of Alkenes

Alkene Structure and Reactivity

9.3K Views

article

7.3 : Degree of Unsaturation

Alkene Structure and Reactivity

6.9K Views

article

7.5 : Relative Stabilities of Alkenes

Alkene Structure and Reactivity

12.7K Views

article

7.6 : Introduction to Electrophilic Addition Reactions of Alkenes

Alkene Structure and Reactivity

6.7K Views

article

7.7 : Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Alkene Structure and Reactivity

10.5K Views

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved