Answered: Make a model of each compound, draw it…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 12CTQ: Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth...

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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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