Trans-2-bromocyclohexanol

Definition

trans-2-bromocyclohexanol is a halohydrin compound formed by the addition of hydrobromic acid (HBr) to the alkene cyclohexene. This addition reaction results in the formation of a bromohydrin, where a bromine atom and a hydroxyl group are added across the double bond in a trans configuration.

5 Must Know Facts For Your Next Test

1. The trans configuration of the bromine and hydroxyl groups in trans-2-bromocyclohexanol means that they are on opposite sides of the cyclohexane ring.
2. The formation of trans-2-bromocyclohexanol involves the anti-addition of HBr to the cyclohexene alkene, where the bromine and hydroxyl groups are added to opposite sides of the double bond.
3. The presence of the bromine atom in trans-2-bromocyclohexanol makes it a useful intermediate in organic synthesis, as the bromine can be further functionalized or replaced with other groups.
4. The stereochemistry of trans-2-bromocyclohexanol is important because it can influence the reactivity and selectivity of subsequent reactions involving this compound.
5. The cyclohexane ring in trans-2-bromocyclohexanol can adopt different conformations, such as the chair or boat conformation, which can affect the overall stability and reactivity of the molecule.

Review Questions

• Describe the mechanism for the formation of trans-2-bromocyclohexanol from cyclohexene and hydrobromic acid (HBr).
  • The formation of trans-2-bromocyclohexanol from cyclohexene and HBr involves an electrophilic addition reaction. First, the electrophilic bromine from HBr attacks the alkene, forming a bromonium ion intermediate. Then, the nucleophilic hydroxide ion from the water in HBr attacks the bromonium ion from the opposite side, resulting in the trans addition of the bromine and hydroxyl groups to the cyclohexene. This anti-addition mechanism leads to the formation of the trans-2-bromocyclohexanol product.
• Explain the importance of the trans stereochemistry in trans-2-bromocyclohexanol and how it can influence subsequent reactions.
  • The trans stereochemistry of the bromine and hydroxyl groups in trans-2-bromocyclohexanol is significant because it determines the overall three-dimensional structure of the molecule. This trans configuration means that the bromine and hydroxyl groups are on opposite sides of the cyclohexane ring, which can affect the reactivity and selectivity of subsequent reactions involving this compound. For example, the trans stereochemistry may influence the stereoselectivity of substitution or elimination reactions, as the bromine and hydroxyl groups can interact differently with incoming nucleophiles or bases depending on their spatial arrangement.
• Analyze the potential applications of trans-2-bromocyclohexanol in organic synthesis, considering its structural features and reactivity.
  • trans-2-Bromocyclohexanol is a valuable intermediate in organic synthesis due to its unique structural features and reactivity. The presence of the bromine atom provides a site for further functionalization, allowing the molecule to be transformed into a wide range of other compounds. Additionally, the trans stereochemistry of the bromine and hydroxyl groups can be leveraged to control the stereochemistry of subsequent reactions, making trans-2-bromocyclohexanol a useful chiral building block. Furthermore, the cyclohexane ring structure and the ability to adopt different conformations can influence the overall reactivity and selectivity of reactions involving this compound. Consequently, trans-2-bromocyclohexanol finds applications in the synthesis of more complex organic molecules, where its versatility and stereochemical control can be exploited to create diverse and functionalized products.

Related terms

Halohydrins: Halohydrins are organic compounds containing both a halogen atom (e.g., bromine, chlorine) and a hydroxyl group (-OH) attached to the same carbon atom.

Addition Reactions: Addition reactions are a class of organic reactions where two or more reactants combine to form a single product, typically by the addition of a molecule across a carbon-carbon double or triple bond.

Stereochemistry: Stereochemistry is the study of the three-dimensional arrangement of atoms in molecules and how this affects their chemical and physical properties.