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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Capitolo 10, Problema 57

Identify A–E.

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Step 1: Analyze the first reaction. The starting compound is cyclohexene, which reacts with bromine (Br₂) in water (H₂O). This is a halohydrin formation reaction. Bromine adds across the double bond, and water provides the hydroxyl group (-OH). The product A is a bromohydrin, where one carbon of the double bond gets a bromine atom and the other gets a hydroxyl group.
Step 2: Identify B. In the halohydrin formation reaction, bromine reacts with water, and one of the byproducts is hydrobromic acid (HBr). Thus, B is HBr.
Step 3: Examine the second reaction. Compound A reacts with hydroxide ion (HO⁻). This is an elimination reaction where the hydroxide ion removes a proton, leading to the formation of an epoxide (C). The bromine atom is eliminated, and the oxygen from the hydroxyl group forms a three-membered ring with the two carbons.
Step 4: Analyze the third reaction. Compound C (the epoxide) reacts with hydroxide ion (HO⁻) in water (H₂O). This is a ring-opening reaction. The hydroxide ion attacks one of the carbons in the epoxide, breaking the ring and forming a diol (D). The two hydroxyl groups (-OH) are added to the carbons that were part of the epoxide ring.
Step 5: Identify E. In the ring-opening reaction, water is used as a solvent, but no additional byproducts are formed. Therefore, E is simply water (H₂O), which remains in the reaction mixture.

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