Make a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity. cis-1,3-dibromocyclohexane
Make a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity. cis-1,3-dibromocyclohexane
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section: Chapter Questions
Problem 2.35P: Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest...
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Question
Make a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity.
cis-1,3-dibromocyclohexane
Expert Solution
Step 1
Asymmetric centre –
- Asymmetric centre is a molecule having a special arrangement of atoms which is not superiposable on its mirror images.
- So, molecule consists of asymmetric (Chiral) carbon atom called as asymmetric centre.
- Chiral carbon atom is a Carbon which bears four different groups (non identical substituents).
- By using these criteria chiral carbon can be predicted from given molecules.
- Molecule with chiral carbon that is asymmetric centre is optically active.
Plane of symmetry:
The plane in molecule which split molecule in to two equal halves.
This is an imaginary plane.
Step 2
Answer of given question:
Structure of cis-1, 3-dibromocyclohexane is as shown below:
Beyond that this compound has two chiral carbons but it will not show the optical activity as it has a plane of symmetry in the molecule. Hence cis-1,3-dibromocyclohexane is optically inactive.
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