/*! 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} 54P Draw a stepwise mechanism for th... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 22: 54P (page 868)

Draw a stepwise mechanism for the following reduction.

Short Answer

Expert verified

Answer

Reduction follows multiple steps:

Step 1

Step 2

Step 3

Step 4

Step by step solution

01

Step-by-Step Solution Step 1: Reducing agents

Esters give alcohol on reduction with strong reducing agents like LiAlH4 .

Cyclic ketones are known as lactones. When treated with strong reducing agents, lactones give alcohol.

02

Reduction of lactone mechanism

In the mechanism, the reagent LiAlH4 reduces the first cyclic ring of lactone to give aldehyde, followed by complete reduction to give alcohol.

Reduction of first lactone ring

Reagent LiAlH4 provides nucleophile H- , which attacks the carbonyl carbon and forms tetrahedral intermediate giving aldehyde.

Formation of aldehyde

The formed aldehyde undergoes complete reduction with LiAlH4 to give alcohol.

Reduction of aldehyde

The second lactone ring is also reduced similarly, giving alcohol.

Reduction of second lactone ring

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

A student tried to carry out the following reaction sequence, but none of diol A was formed. Explain what was wrong with this plan, and design a successful stepwise synthesis of A.

What product is formed when each compound is treated with either LiAlH4 (followed by H2O ), or NaBH4 in CH3OH ?

Draw two different ways to prepare each ketone from an acid chloride and an organocuprate reagent.

a.

b.
  1. What orbitals are used to form the indicated bonds in 伪-sinensal?
  2. In what type of orbitals do the lone pairs on Oreside?

Question: Explain why the boiling point of CH3CONH2(221掳C) is significantly higher than the boiling point ofCH3CO2H .
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Kinetics

Read Explanation

Chemical Analysis

Read Explanation

Making Measurements

Read Explanation

The Earths Atmosphere

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.