Select your language

Suggested languages for you:
Log In Start studying!
Answers without the blur. Just sign up for free and you're in → Illustration

Q.53.

Expert-verified
Organic Chemistry
Found in: Page 128

Short Answer

Question: For each compound drawn below:

a. Label each OH, Br, andgroup as axial or equatorial.

b. Classify each conformation as cis or trans.

c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.

d. Draw the second possible chair conformation for each compound.

Answer

a.

b.

c.

d.

See the step by step solution

Step by Step Solution

Step 1: Chair conformation

The chair conformation is considered the most stable due to its low energy. The conformation has six (axial or equatorial) sites.

The axial and equatorial sites are represented as:

Blue represents the H-equatorial and black represents the H-axial

Step 2: Cis and trans configurations in the chair conformation

The Cis conformation is determined when two sites have axial (can be up or down) substitution or equatorial substitution.

The trans conformation is obtained when two sites have one axial and one equatorial substitution.

Step 3: Explanation

a. The axial group is perpendicular to the plane, and the equatorial groups are parallel to the plane.

Axial and equatorial (eq)

Axial and equatorial (eq) substituents

Axial and equatorial (eq) substituents

b. The cis conformation has only up or only down substitution.

The trans conformation has up and down conformations.

Trans chair conformation

Cis chair conformation

Trans chair conformation

c.

In the wedge dash structure of the chair conformation, the up substituent (it may be axial or equatorial) is shown above the plane, and the down substituents are shown below the plane.

Wedge dash structure

Wedge dash structure

Wedge dash structure

d.

When one chair conformation flips to the other, the groups are interchanged.

Ring flipping

Ring flipping

Ring flipping

Recommended explanations on Chemistry Textbooks

94% of StudySmarter users get better grades.

Sign up for free
94% of StudySmarter users get better grades.