/*! 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} Q58. Question: Draw a stepwise mechan... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 23: Q58. (page 924)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Answer

Stepwise mechanism




Step by step solution

01

 Step 1: Carbonyl groups forming enolate

The carbonyl groups are electron-withdrawing groups and so any hydrogen(s) present at 伪-position are highly acidic in nature.

Those acidic 伪-H can easily be removed in presence of a base and with the formation of a stable enolate.

The CH2 group containing acidic hydrogen(s) is called the active methylene group.

02

Mechanism

The given reaction

Step-by-step mechanism:

  • The compound has an active methylene group which is located in between two strong electron-withdrawing -COOEt groups. The base -OEt easily takes it to generate a stable enolate.


Formation of stable enolate

  • The enolate attacks at the epoxide and cleaves the ring by breaking the C-O bond to generate an alkoxide ion.


Generation of alkoxide ion

  • The negatively charged oxygen atom attacks at the C=O center with the removal of ethoxide anion to form a five-member cyclic ester, called lactone.


Formation of lactone

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 91影视!

One App. One Place for Learning.

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

Get started for free

Most popular questions from this chapter

Question:What alkyl halides are needed to prepare each ketone using the acetoacetic ester synthesis?

Question: Draw a stepwise mechanism for the following reaction.

Question: Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Brforms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from thejack-o鈥�-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?

Question: Which C-Hbonds in the following molecules are acidic because the resulting conjugate base is resonance stabilized?

Question: A key step in the synthesis of the narcotic analgesic meperidine (trade name Demerol) is the conversion of phenyl acetonitrile to X. (a) What is the structure of X? (b) What reactions convert X to meperidine?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Inorganic Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Physical Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.