Given that Grignard reagents react with oxetane to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. The reason for the difference in reactivity between oxenate and ethylene oxide is to be suggested. Concept introduction: The ring size of cyclic compound has a great influence on its reactivity. Normally cyclic compounds with rings made up of 3 or 4 of carbon atoms are less stable and react fast as the strain in the molecule is relieved when the ring opens by reaction. To suggest: The reason for the difference in reactivity between oxenate and ethylene oxide when they are treated with Grignard reagents. Oxenate reacts much slower than ethylene oxide.

Question

Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.

Answer 1

Question

Chapter 18.SE, Problem 61GP

Interpretation Introduction

Interpretation:

Given that Grignard reagents react with oxetane to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. The reason for the difference in reactivity between oxenate and ethylene oxide is to be suggested.

Concept introduction:

The ring size of cyclic compound has a great influence on its reactivity. Normally cyclic compounds with rings made up of 3 or 4 of carbon atoms are less stable and react fast as the strain in the molecule is relieved when the ring opens by reaction.

To suggest:

The reason for the difference in reactivity between oxenate and ethylene oxide when they are treated with Grignard reagents. Oxenate reacts much slower than ethylene oxide.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.

Provide a two step method to distinguish between the following compounds. (Propanal, butanal, butanone, propanone). Explain your choice of reagents and your expected results.

Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.