Given that Dieckmann cyclization of 3-methylheptanedioate gives a mixture of two β keto esters as products. Their structures are to be given and the formation of a mixture of two β keto esters as product is to be explained. Concept introduction: Diesters can undergo intramolecular cyclization reactions to yield cyclic esters. This reaction is called Dieckmann cyclization. In this reaction 1,6-diesters give a five membered cyclic β-keto esters while 1,7-diesters give a six membered cyclic β-keto esters. One of the ester groups is converted into an enolate anion, which then carries out a nucleophilic acyl substitution on the second ester group at the other end of the molecule. To give: The structures of two β keto esters obtained as products in the Dieckmann cyclization of 3-methylheptanedioate are to be given. To explain: Why a mixture of two β keto esters is formed in this reaction.

Question

Curved arrows are used to illustrate the flow of electrons. Using the provided structures, draw the curved arrows that epict the mechanistic steps for the proton transfer between a hydronium ion and a pi bond. Draw any missing organic structures in the empty boxes. Be sure to account for all lone-pairs and charges as well as bond-breaking and bond-making steps. 2 56°F Mostly cloudy F1 Drawing Arrows > Q Search F2 F3 F4 ▷11 H. H : CI: H + Undo Reset Done DELL

Answer 1

Question

Chapter 23.9, Problem 15P

Interpretation Introduction

Interpretation:

Given that Dieckmann cyclization of 3-methylheptanedioate gives a mixture of two β keto esters as products. Their structures are to be given and the formation of a mixture of two β keto esters as product is to be explained.

Concept introduction:

Diesters can undergo intramolecular cyclization reactions to yield cyclic esters. This reaction is called Dieckmann cyclization. In this reaction 1,6-diesters give a five membered cyclic β-keto esters while 1,7-diesters give a six membered cyclic β-keto esters. One of the ester groups is converted into an enolate anion, which then carries out a nucleophilic acyl substitution on the second ester group at the other end of the molecule.

To give:

The structures of two β keto esters obtained as products in the Dieckmann cyclization of 3-methylheptanedioate are to be given.

To explain:

Why a mixture of two β keto esters is formed in this reaction.

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