For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]
(e)

Verified step by step guidance

1. Step 1: Understand the concept of chair flipping in cyclohexane. When a chair conformation flips, axial substituents become equatorial, and equatorial substituents become axial. However, the substituents remain attached to the same carbon atoms.
2. Step 2: Identify the substituents and their positions on the original chair conformation. In this case, there is a bromine (Br) substituent at carbon 3 in the axial position and another bromine (Br) substituent at carbon 4 in the equatorial position.
3. Step 3: Draw the flipped chair conformation. Ensure that the carbon numbering remains consistent (carbon 1 through carbon 6) and the overall structure of the cyclohexane ring is preserved.
4. Step 4: Place the substituents on the flipped chair conformation. For carbon 3, the bromine substituent that was axial in the original chair conformation will now be equatorial. For carbon 4, the bromine substituent that was equatorial in the original chair conformation will now be axial.
5. Step 5: Double-check the positions of the substituents to ensure accuracy. Verify that the axial/equatorial designations have been correctly swapped and that the substituents remain attached to their respective carbons.

Key Concepts

Chair Conformation

Chair conformation is a three-dimensional representation of cyclohexane that minimizes steric strain. In this conformation, the carbon atoms are arranged in a way that allows for staggered bonds, making it the most stable form of cyclohexane. Understanding chair conformation is essential for visualizing how substituents are positioned in space.

Axial and Equatorial Positions

In chair conformations, substituents can occupy two types of positions: axial and equatorial. Axial substituents are oriented perpendicular to the plane of the ring, while equatorial substituents are oriented parallel to the plane. The designation of these positions changes when the chair conformation is flipped, which is crucial for predicting the stability of different substituent arrangements.

Flipping the Chair

Flipping the chair refers to the process of converting one chair conformation of cyclohexane into another. This involves rotating the ring structure, which causes axial substituents to become equatorial and vice versa. This concept is important for understanding how the spatial arrangement of substituents affects the overall stability and reactivity of cyclohexane derivatives.