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Acyl substitution, nucleophilic

CARBOXYLIC ACID DERIVATIVES NUCLEOPHILIC ACYL SUBSTITUTION... [Pg.830]

Carboxylic Acid Derivatives Nucleophilic Acyl Substitution... [Pg.831]

Both stages involve more than one step and these steps differ in detail among the various carboxylic acid derivatives and for different reaction conditions This chapter is organized to place the various nucleophilic acyl substitutions into a common mechanis tic framework and to point out the ways m which individual classes differ from the rest... [Pg.831]

IS general for nucleophilic acyl substitution and well worth remembering The range of reactivities is quite large a factor of about 10 m relative rate separates acyl chlorides from amides... [Pg.834]

The features that complicate the mechanism of nucleophilic acyl substitution are almost entirely related to acid-base chemistry We try to keep track as best we can of the form m which the various species—reactants intermediates and prod nets—exist under the reaction conditions... [Pg.837]

Each one of these can proceed to the product of nucleophilic acyl substitution Dissociation of TI—H ... [Pg.837]

Mechanisms for a number of nucleophilic acyl substitutions will appear m the sec tions that follow It is better to look for the important ways m which they are similar than to search for details m which they differ... [Pg.838]

The sp hybridized carbon of an acyl chloride is less sterically hindered than the sp hybridized carbon of an alkyl chloride making an acyl chloride more open toward nude ophilic attack Also unlike the 8 2 transition state or a carbocation intermediate m an Stvfl reaction the tetrahedral intermediate m nucleophilic acyl substitution has a stable arrangement of bonds and can be formed via a lower energy transition state... [Pg.841]

Conversions of acid anhydrides to other carboxylic acid derivatives are illustrated m Table 20 2 Because a more highly stabilized carbonyl group must result m order for nucleophilic acyl substitution to be effective acid anhydrides are readily converted to carboxylic acids esters and amides but not to acyl chlorides... [Pg.842]

Nucleophilic acyl substitutions at the ester carbonyl group are summarized m Table 20 5 on page 849 Esters are less reactive than acyl chlorides and acid anhydrides Nude ophilic acyl substitution m esters especially ester hydrolysis has been extensively mves tigated from a mechanistic perspective Indeed much of what we know concerning the general topic of nucleophilic acyl substitution comes from studies carried out on esters The following sections describe those mechanistic studies... [Pg.846]

The mechanism of acid catalyzed ester hydrolysis is presented m Figure 20 4 It IS precisely the reverse of the mechanism given for acid catalyzed ester formation m Section 19 14 Like other nucleophilic acyl substitutions it proceeds m two stages A... [Pg.849]

The other process is a nucleophilic acyl substitution triggered by hydroxide attack at the carbonyl group... [Pg.854]


See other pages where Acyl substitution, nucleophilic is mentioned: [Pg.830]    [Pg.834]    [Pg.836]    [Pg.837]    [Pg.842]    [Pg.843]    [Pg.845]   
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ARBOXYLIC ACID DERIVATIVES NUCLEOPHILIC ACYL SUBSTITUTION

Abbreviated mechanism, nucleophilic acyl substitution reactions

Acid Derivatives Nucleophilic Acyl Substitution

Acid Derivatives Nucleophilic Acyl Substitution Reactions

Acid Derivatives and Nucleophilic Acyl Substitution Reactions

Acid anhydride nucleophilic acyl substitution reactions

Acid anhydride, amides from nucleophilic acyl substitution

Acid catalysis nucleophilic acyl substitution

Acid catalysis of nucleophilic acyl substitution

Acid chloride, alcohols from nucleophilic acyl substitution

Acid chlorides nucleophilic acyl substitution reactions

Acids and Their Derivatives — Nucleophilic Acyl Substitution

Acyl group nucleophilic substitution

Acyl nucleophilic substitution, carbanion

Acyl nucleophilic substitution, carbanion intermediates

Acyl substitution

Acyl substitution by nucleophilic addition-elimination

Acylation Nucleophilic acyl substitution

Acylation Nucleophilic acyl substitution

Addition-Elimination Mechanism of Nucleophilic Acyl Substitution

Alcoholysis (nucleophilic acyl substitution

Amide , amines from nucleophilic acyl substitution

Amide nucleophilic acyl substitution reactions

Aminolysis (nucleophilic acyl substitution

Biological reaction, alcohol nucleophilic acyl substitution

Carbanions nucleophilic acyl substitution

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions

Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution

Carboxylic acid derivatives nucleophilic acyl substitution

Carboxylic acid derivatives nucleophilic acyl substitution reactions

Carboxylic acid nucleophilic acyl substitution

Carboxylic acid nucleophilic acyl substitution reactions

Ester nucleophilic acyl substitution reactions

General Mechanism for Nucleophilic Acyl Substitution

Hell-Volhard-Zelinskii reaction nucleophilic acyl substitution

Hydrolysis (nucleophilic acyl substitution

Hydrolysis (nucleophilic acyl substitution amides

Hydrolysis (nucleophilic acyl substitution esters

Hydrolysis (nucleophilic acyl substitution nitriles

Hydrolysis (nucleophilic acyl substitution proteins

Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution

Intermolecular nucleophilic acyl substitution

Intramolecular nucleophilic acyl substitution

Introduction to Nucleophilic Acyl Substitution

Mechanism nucleophilic acyl substitution

Nucleophiles Nucleophilic acyl substitution

Nucleophiles Nucleophilic acyl substitution

Nucleophiles acylation

Nucleophilic Acyl Substitution Reactions of Carboxylic Acids

Nucleophilic Acyl Substitution in Acid Anhydrides

Nucleophilic Acyl Substitution in an Anhydride

Nucleophilic Acyl Substitution in the Basic Hydrolysis of an Ester

Nucleophilic Substitution in Acyl Chlorides

Nucleophilic acyl substitution abbreviated mechanism

Nucleophilic acyl substitution acid anhydrides

Nucleophilic acyl substitution acid chlorides

Nucleophilic acyl substitution acid halides

Nucleophilic acyl substitution amides

Nucleophilic acyl substitution carbonyl compound

Nucleophilic acyl substitution carboxylic acids and

Nucleophilic acyl substitution defined

Nucleophilic acyl substitution esters

Nucleophilic acyl substitution general mechanism

Nucleophilic acyl substitution in esters

Nucleophilic acyl substitution kinds

Nucleophilic acyl substitution of amides

Nucleophilic acyl substitution of carboxylic acid anhydrides

Nucleophilic acyl substitution of esters

Nucleophilic acyl substitution of thioesters

Nucleophilic acyl substitution position

Nucleophilic acyl substitution reaction acid halides

Nucleophilic acyl substitution reaction biological example

Nucleophilic acyl substitution reaction kinds

Nucleophilic acyl substitution reaction reactivity

Nucleophilic acyl substitution reactions biological

Nucleophilic acyl substitution reactions derivatives

Nucleophilic acyl substitution reactions general reaction

Nucleophilic acyl substitution reactions leaving groups

Nucleophilic acyl substitution reactions of carboxylic acid derivatives

Nucleophilic acyl substitution reactions relative reactivity

Nucleophilic acyl substitution reactions summary

Nucleophilic acyl substitution reactions tetrahedral intermediate

Nucleophilic acyl substitution reactivity

Reaction mechanisms nucleophilic acyl substitution

Reactions of Carboxylic Acids and Derivatives Nucleophilic Acyl Substitution

Substitution reactions nucleophilic acyl

Summary of Nucleophilic Acyl Substitution Reactions

The Mechanism of Acid-Catalyzed Esterification Nucleophilic Acyl Substitution

Thiazoles, 2-acyl nucleophilic substitution

Thioesters nucleophilic acyl substitution

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