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Q.22.

Expert-verified
Organic Chemistry
Found in: Page 128

Short Answer

Question: Using the cyclohexane with the C’s numbered as shown, draw a chair form that fits each description.

a. The ring has an axial group at C1 and an equatorial OH on C2.

b. The ring has an equatorial group on C6 and an axial OH group on C4.

c. The ring has equatorial OH groups on C1, C2, and C5.

Answer

a.

b.

c.

See the step by step solution

Step by Step Solution

Step 1: Identification of axial and equatorial positions

In the given structure, carbons 1, 3, and 5 are up on the ring while carbons 2,4, and 6 are down.

The hydrogen atoms attached to carbons 1,3, and 5 are present above the plane of the ring and are known as axial hydrogens. The other 3 axial hydrogen atoms are present below the ring attached to carbons 2,3, and 4.

The axial hydrogen atoms on cyclohexane are shown in the structure below:

Axial hydrogens on cyclohexane

The equatorial hydrogen atoms on cyclohexane are shown in the following structure:

Equatorial hydrogens

Different groups can be attached to the carbon atoms by replacing the hydrogen atoms on cyclohexane. These substituents can be attached at the axial or equatorial positions.

Step 2: Groups attached to the carbon atoms of cyclohexane at the equatorial and axial positions

a. The axial group at C1 and the equatorial -OH at C2 are shown in the following structure:

-OH at C2 and at C1

b. The equatorial group at C6 and the axial -OH group at C4 are shown in the structure below:

-OH at C5 and at C6

c. The -OH groups at the equatorial positions on C1, C2, and C5 are shown in the following structures:

Equatorial -OH groups at C1,C2, and C5

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