/*! 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} 64P Draw a stepwise mechanism for th... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Draw a stepwise mechanism for the following reaction

Short Answer

Expert verified

The movement or shift or pi-electrons within a compound in order to increase the stability of the compound is referred as delocalization.

The lone pair of electrons delocalized as proton is abstracted by the double-bonded carbon atom.

Delocalization of pi-electrons of the substrate

Step by step solution

01

Delocalization

The movement or shift or pi-electrons within a compound in order to increase the stability of the compound is referred as delocalization.

The lone pair of electrons delocalized as proton is abstracted by the double-bonded carbon atom.

Delocalization of pi-electrons of the substrate

02

Resonance Structure

The cation is stabilized by resonance as the electrons shift back to the nitrogen atom and the nucleophilic attack of a water molecule form a new C-O bond.

Resonance stabilization

03

Deprotonation

The proton is removed to stabilize the ion.

Deprotonation

04

Protonation

The lone pair of electrons on nitrogen atom would abstract another proton giving a protonated amine.

Protonation

05

Stabilisation

The lone pair of electrons on the oxygen atom of the -OH bond shifts as the C-N bond breaks thereby stabilising the cation.

Stabilisation of the ion

06

Deprotonation

The proton leaves as the C=O double bond is formed.

07

Protonation

The amine group is protonated to form the required product,

Formation of the product

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

Most popular questions from this chapter

Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan-2-one.

a. Suggest a structure for brevicomin.

b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

¶Ù°ù²¹·É t³ó±ð p°ù´Ç»å³Ü³¦³Ù f´Ç°ù³¾±ð»å w³ó±ð²Ô C±á3CH2CH2CH2NH2reacts with each carbonyl compound in the presence of mild acid.

a.

b.

c.

Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).

a. Which carbonyl compound is more stable?

b. Which compound forms the higher percentage of hydrate at equilibrium?

c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?

Explain your reasoning in each part.

Besides the tert-butyldimethylsilyl ethers introduced in Chapter 20, there are many other widely used alcohol protecting groups. For example, an alcohol such as cyclohexanol can be converted to a methoxy methyl ether (a MOM protecting group) by treatment with base and chloromethyl methyl ether, . The protecting group can be removed by treatment with aqueous acid.

a. Write a stepwise mechanism for the formation of a MOM ether from cyclohexanol.

b. What functional group comprises a MOM ether?

c. Besides cyclohexanol, what other products are formed by aqueous hydrolysis of the MOM ether? Draw a stepwise mechanism that accounts for formation of each product.

See all solutions

Recommended explanations on Chemistry Textbooks

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.