It is to be explained why the attempt to synthesize an epoxide according to the given reaction scheme failed. Concept introduction: Epoxides are three membered ring ethers and can be made using halohydrins. Halohydrins are the compounds containing a halogen and a hydroxyl group on adjacent carbon atoms. When a halohydrin is treated with a strong base, the strong base deprotonates the hydrogen atom in the hydroxyl group in halohydrin. The negatively charged oxygen atom then attacks the carbon atom to which the bromine or halogen atom is attached to form an epoxide via an S N 2 reaction pathway. In the most stable form of substituted cyclohexane, the bulkiest group occupies the equatorial position. The substituents attached to the cyclohexane are cis if they lie on the same side of the plane of the ring, and they are trans if they lie on the opposite side of the plane of the ring.

Question

Want to see the full answer?

Answer 1

Question

Chapter 10, Problem 10.51P

Interpretation Introduction

Interpretation:

It is to be explained why the attempt to synthesize an epoxide according to the given reaction scheme failed.

Concept introduction:

Epoxides are three membered ring ethers and can be made using halohydrins. Halohydrins are the compounds containing a halogen and a hydroxyl group on adjacent carbon atoms. When a halohydrin is treated with a strong base, the strong base deprotonates the hydrogen atom in the hydroxyl group in halohydrin. The negatively charged oxygen atom then attacks the carbon atom to which the bromine or halogen atom is attached to form an epoxide via an SN2 reaction pathway.

In the most stable form of substituted cyclohexane, the bulkiest group occupies the equatorial position. The substituents attached to the cyclohexane are cis if they lie on the same side of the plane of the ring, and they are trans if they lie on the opposite side of the plane of the ring.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv

Don't used Ai solution

I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."