1,3-dibromocyclohexane

Definition

1,3-dibromocyclohexane is a cyclic organic compound consisting of a six-membered carbon ring with two bromine atoms attached at the 1 and 3 positions. This molecule is important in understanding the concepts of axial and equatorial bonds in cyclohexane derivatives.

5 Must Know Facts For Your Next Test

1. The bromine atoms in 1,3-dibromocyclohexane are in a trans configuration, meaning they are on opposite sides of the cyclohexane ring.
2. The presence of the bromine atoms causes the cyclohexane ring to prefer a chair conformation, which minimizes steric interactions.
3. In the chair conformation, the bromine atoms occupy equatorial positions, which is the more stable arrangement.
4. Axial positions in 1,3-dibromocyclohexane are less favorable due to the increased steric hindrance between the bromine atoms and the neighboring hydrogen atoms.
5. The equatorial arrangement of the bromine atoms in 1,3-dibromocyclohexane is the predominant and more stable configuration.

Review Questions

• Explain the preferred conformation of 1,3-dibromocyclohexane and how it relates to the positioning of the bromine atoms.
  • The presence of the two bromine atoms in the 1,3-positions of the cyclohexane ring causes the molecule to prefer a chair conformation. In this conformation, the bromine atoms occupy equatorial positions, which is the more stable arrangement. This is because the equatorial positions minimize steric interactions between the bulky bromine atoms and the neighboring hydrogen atoms, resulting in a lower overall energy state for the molecule.
• Describe the difference between axial and equatorial bonds in the context of 1,3-dibromocyclohexane.
  • In 1,3-dibromocyclohexane, the bromine atoms are oriented in the equatorial positions, which are perpendicular to the central axis of the cyclohexane ring. Axial bonds, on the other hand, are parallel to the central axis. The equatorial arrangement is more favorable for 1,3-dibromocyclohexane due to the reduced steric hindrance between the bromine atoms and the neighboring hydrogen atoms, whereas the axial positions would result in increased steric interactions and a less stable configuration.
• Analyze how the position of the bromine atoms in 1,3-dibromocyclohexane affects the overall stability and reactivity of the molecule.
  • The placement of the bromine atoms at the 1 and 3 positions of the cyclohexane ring in 1,3-dibromocyclohexane significantly influences the stability and reactivity of the molecule. The trans configuration of the bromine atoms, along with their preference for equatorial positions, results in a more stable chair conformation that minimizes steric interactions. This stable arrangement affects the reactivity of the molecule, as the bromine atoms are less likely to undergo substitution or elimination reactions compared to a molecule with bromine atoms in less favorable positions. The overall stability and reduced reactivity of 1,3-dibromocyclohexane can be attributed to the strategic positioning of the bromine atoms within the cyclohexane framework.

Related terms

Cyclohexane:

A saturated six-membered carbon ring with the chemical formula C6H12.

Axial Bonds: Bonds in a cyclohexane ring that are oriented parallel to the central axis of the ring.

Equatorial Bonds: Bonds in a cyclohexane ring that are oriented perpendicular to the central axis of the ring.