Wohl-Ziegler Reaction

Definition

The Wohl-Ziegler reaction is a method for the allylic bromination of alkenes, where a bromine atom is introduced at the carbon adjacent to the carbon-carbon double bond. This reaction is an important tool in organic synthesis for the preparation of alkyl halides from alkenes.

5 Must Know Facts For Your Next Test

1. The Wohl-Ziegler reaction typically uses N-bromosuccinimide (NBS) as the bromine source and a radical initiator, such as benzoyl peroxide or UV light, to generate bromine radicals.
2. The reaction proceeds through a radical mechanism, where the bromine radical abstracts a hydrogen atom from the allylic position of the alkene, forming a stabilized allylic radical intermediate.
3. The allylic radical then reacts with a bromine molecule to give the final allylic bromination product.
4. The Wohl-Ziegler reaction is regioselective, meaning it selectively brominated the carbon adjacent to the double bond, rather than other positions on the alkene.
5. This reaction is useful for the synthesis of allylic halides, which are important intermediates in organic synthesis and can be further transformed into a variety of other functional groups.

Review Questions

• Describe the key steps of the Wohl-Ziegler reaction mechanism.
  • The Wohl-Ziegler reaction proceeds through a radical mechanism. First, the radical initiator (e.g., benzoyl peroxide or UV light) generates bromine radicals from the N-bromosuccinimide (NBS) reagent. These bromine radicals then abstract a hydrogen atom from the allylic position of the alkene, forming a stabilized allylic radical intermediate. Finally, the allylic radical reacts with a bromine molecule to give the final allylic bromination product.
• Explain the regioselectivity of the Wohl-Ziegler reaction and why it is important.
  • The Wohl-Ziegler reaction is regioselective, meaning it selectively brominated the carbon adjacent to the double bond, rather than other positions on the alkene. This regioselectivity is important because it allows for the targeted synthesis of allylic halides, which are valuable intermediates in organic synthesis. The allylic position is preferred due to the stabilization of the allylic radical intermediate, which is a key step in the reaction mechanism.
• Discuss the applications and importance of the Wohl-Ziegler reaction in the context of preparing alkyl halides from alkenes.
  • The Wohl-Ziegler reaction is a crucial tool in organic synthesis for the preparation of alkyl halides from alkenes. Allylic halides generated by this reaction can be further transformed into a variety of other functional groups, making them versatile intermediates. This reaction allows for the selective introduction of a bromine atom at the carbon adjacent to the double bond, which is a common structural motif in many organic compounds. The Wohl-Ziegler reaction's regioselectivity and the ability to form allylic halides make it an indispensable method for the synthesis of complex organic molecules.

Related terms

Allylic Bromination: The selective substitution of a hydrogen atom with a bromine atom at the carbon adjacent to a carbon-carbon double bond.

Radical Mechanism: A reaction pathway involving the formation and reactions of free radical intermediates.

N-Bromosuccinimide (NBS): A common reagent used in the Wohl-Ziegler reaction to generate bromine radicals and facilitate the allylic bromination.