Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Reaction of the alkene below with bromine in water gives a cyclic bromo ether instead of the expected bromohydrin.

The chemical reaction depicted in the image involves the transformation of an organic molecule.

Starting Material:
- The structure of the starting material is H₂C=CHCH₂CH₂CH₂OH, which is an alcohol with an alkene group, specifically 5-hexen-1-ol.

Reagents:
- Br₂ (bromine)
- H₂O (water)

Product:
- The product formed is a cyclic ether with a bromoalkane side chain. The structure shows a tetrahydrofuran ring with a bromomethyl group attached, specifically 3-bromo-oxolane.

Instruction:
- Propose a structure for the first (ionic) intermediate in the reaction.

Explanation:
The reaction likely involves the formation of a halohydrin intermediate through the anti-addition of Br₂ in the presence of water. The intermediate may involve a bromonium ion which then undergoes ring closure with participation from the hydroxyl group, resulting in the formation of the cyclic ether.
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Transcribed Image Text:The chemical reaction depicted in the image involves the transformation of an organic molecule. Starting Material: - The structure of the starting material is H₂C=CHCH₂CH₂CH₂OH, which is an alcohol with an alkene group, specifically 5-hexen-1-ol. Reagents: - Br₂ (bromine) - H₂O (water) Product: - The product formed is a cyclic ether with a bromoalkane side chain. The structure shows a tetrahydrofuran ring with a bromomethyl group attached, specifically 3-bromo-oxolane. Instruction: - Propose a structure for the first (ionic) intermediate in the reaction. Explanation: The reaction likely involves the formation of a halohydrin intermediate through the anti-addition of Br₂ in the presence of water. The intermediate may involve a bromonium ion which then undergoes ring closure with participation from the hydroxyl group, resulting in the formation of the cyclic ether.
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