/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q88P Propose a mechanism for the foll... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Propose a mechanism for the following reaction.

Short Answer

Expert verified

The proposed mechanism is shown below:

Step by step solution

01

Step-by-Step SolutionStep 1: Dieckmann condensation

It is an intramolecular Claisen condensation of a compound when two ester groups undergo intramolecular reaction giving a five-membered ring product.Dieckmann condensation converts 1,6-diester to five membered ring βketo ester.

02

Explanation of the mechanism

The mechanism is shown below:

Proposed mechanism

In the first step two ester containing compounds fused to form 1,6-diester. A base(CH3O-)removes proton fromcarbon of diester forming an enolate ion in the fourth step. Then an intramolecular condensation reaction adds enolate ions to the carbonyl carbon of the estergroup forming a five membered ring. Thebond reforms by eliminatingOCH3group and leaving a proton asCH3OH. In the last step of the reaction mechanism, keto group gets protonated and forms five membered βketo ester.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Study anywhere. Anytime. Across all devices.