Chapter 21: Carboxylic Acid Derivatives

Hydrolysis of Acid Derivatives (21-7) This reaction is the reason all of these compounds are considered acid derivativesbecause they produce carboxylic acids upon hydrolysis This reaction can be performed under acidic or basic conditions Acid Chlorides/Anhydrides These two compounds are so reactive that the

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Reaction of Glycidyl Methacrylate at the Hydroxyl and

Transesterification and epoxide ring-opening reactions are two mechanism routes that explain chemical modifications of macromolecules by glycidyl methacrylate (GMA) Although the coupling reaction of the GMA with macromolecules has widely been investigated there are still mechanisms that remain to be explained when GMA is processed in an aqueous solution at

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The Mechanisms of Some Reactions of Thiolsulfinates

THE MECHANISMS OF SOME REACTIONS OF THIOLSULFINATES (SULFENIC ANHYDRIDES) INTRODUCTION Two types of compounds of the general formula R(S2O)R are referred to in the literature The first are the anhydrides of sul- fenic acids RSOH formed by the hydrolysis of sulfenyl chlorides

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Carboxyl Derivative Reactivity

Of these lithium aluminum hydride often abbreviated LAH is the most useful for reducing carboxylic acid derivatives Thanks to its high reactivity LAH easily reduces all classes of carboxylic acid derivatives generally to the –1 oxidation state Acids esters anhydrides and acyl chlorides are all reduced to 1-alcohols and this method

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Carboxylic Acid Derivatives

However carboxylic acids do not spontaneously condense through water elimination Instead the synthesis of carboxylic acid anhydrides may for instance be achieved by treating carboxylate anions with acyl chlorides Fig 4 Synthesis of heptanoic acid anhydride Much like in the Fischer esterification the mechanism of this reaction is an addition-elimination mechanism in which

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Acid Derivatives

No hydrogen bond exists in acid chlorides anhydrides or esters unless there is an -OH group somewhere Amides can hydrogen bond because of the N-H group In fact hydrogen bonding involving the amide backbone of polypeptides form the secondary structure of proteins Amides have higher boiling points than the other acid derivatives

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How would sulfuric acid and water react?

The reaction of water (H2O) and sulphuric acid (H2SO4) is very exothermic and gives out heat (however this answer is in accordance with school textbooks In real cases the reaction of even 98% pure H2SO4 with water isn't too much exothermic) If w

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Amides Esters and Anhydrides

MCAT Organic Chemistry Review Carboxylic Acid Derivatives 9 1 Amides Esters and Anhydrides Amides esters and anhydrides are all carboxylic acid derivatives Each of these is formed by a condensation reaction with a carboxylic acid—a reaction that combines two molecules into one while losing a small molecule In this case the small

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Carboxylic Acid Derivatives

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions - Section 20 of Organic Chemistry Notes is 27 pages in length (page 20-1 through page 20-27) and covers ALL you'll need to know on the following lecture/book topics: SECTION 20 – Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions

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Organic acid anhydride

Acid anhydrides tend to be less electrophilic than acyl chlorides and only one acyl group is transferred per molecule of acid anhydride which leads to a lower atom efficiency The low cost however of acetic anhydride makes it a common choice for acetylation reactions Applications and occurrence of acid anhydrides Illustrative acid anhydrides

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Reactions of Carboxylic Acid Derivatives I

amines with acyl chlorides and anhydrides in aqueous sodium hydroxide solution! Not only is the amine more nucleophilic than water but the acylating reagent is generally not soluble in or miscible with water reducing the rate of its hydrolysis No acylation reactions of amides were shown in these problems The most important such

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Preparation of Acid Chlorides Hydrolysis of Acid Chlorides

Preparation of Acid Chlorides Acid chlorides are prepared from carboxylic acids by reaction with thionyl chloride (SOCl 2) by a mechanism we will not discuss now ROH O SOCl2 RCl O SO2 HCl Hydrolysis of Acid Chlorides Acid chlorides react under acidic or basic conditions to yield carboxylic acids This hydrolysis reaction is a typical nucleophilic acyl substitution Acid halides anhydrides

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Carboxylic acid derivatives: Acyl Chlorides and Acid

2018-11-06Carboxylic acid derivatives: Acyl Chlorides and Acid Anhydrides Acid Anhydrides ethanoic anhydride CH3 C O O CH3 C O Acyl Chlorides CH3 C O Cl ethanoyl chloride Acid anhydrides have a similar reactivity to acyl chlorides and therefore bring about the same changes in functional groups The main difference is the by-products Acyl chlorides

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Carboxylic acid derivatives: Acyl Chlorides and Acid

2018-04-06Carboxylic acid derivatives: Acyl Chlorides and Acid Anhydrides Acid Anhydrides ethanoic anhydride CH3 C O O CH3 C O Acyl Chlorides CH3 C O Cl ethanoyl chloride Acid anhydrides have a similar reactivity to acyl chlorides and therefore bring about the same changes in functional groups The main difference is the by-products Acyl chlorides

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Acid Derivatives

No hydrogen bond exists in acid chlorides anhydrides or esters unless there is an -OH group somewhere Amides can hydrogen bond because of the N-H group In fact hydrogen bonding involving the amide backbone of polypeptides form the secondary structure of proteins Amides have higher boiling points than the other acid derivatives

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CHM 331 : General Organic Chemistry

• forcing conditions usually means boiling water or extended reaction times Acid catalyzed mechanism • this mechanism was covered in the carboxylic acids notes in the section acid synthesis by hydrolysis of nitriles • nitrile hydrolysis proceeds via an amide which is further hydrolyzed under acidic conditions to a carboxylic acid

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Organic acid anhydride

Acid anhydrides tend to be less electrophilic than acyl chlorides and only one acyl group is transferred per molecule of acid anhydride which leads to a lower atom efficiency The low cost however of acetic anhydride makes it a common choice for acetylation reactions Applications and occurrence of acid anhydrides Illustrative acid anhydrides

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An Extremely Powerful Acylation Reaction of Alcohols with

Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides Highly functionalized primary secondary tertiary and allylic alcohols and phenols were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions

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Synthesis of Carboxylic Acids

From Acid Chlorides Anhydrides Esters or Amides: Hydrolysis Reactions of Carboxylic Acids 9 Reaction as a proton Acid (Section 20-4 20-5) R O O OH-+ H-X (proton acid) NaOH (or other bases including amines) Na carboxylate salt (basic) • Mechanism: Required (deprotonation) • Reverse Mechanism: Required (protonation) • Carboxylic acids are

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The Mechanisms of Some Reactions of Thiolsulfinates

THE MECHANISMS OF SOME REACTIONS OF THIOLSULFINATES (SULFENIC ANHYDRIDES) INTRODUCTION Two types of compounds of the general formula R(S2O)R are referred to in the literature The first are the anhydrides of sul- fenic acids RSOH formed by the hydrolysis of sulfenyl chlorides

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KINETICS AND MECHANISM OF CURING EPOXY/ANHYDRIDE

reactions take place with and without a catalyst Reaction between epoxy groups and hydroxyls was 1 INTRODUCTION Epoxy resins cured by anhydrides usually have better properties than resins cured by amines They are less poisonous display a higher glass transition temperature and absorb less water lower reaction

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3 4 5 Compounds Containing the Carbonyl Group

know the reactions of water alcohols ammonia and primary amines with acyl chlorides and acid anhydrides understand the mechanism of nucleophilic addition - elimination reactions between water alcohols ammonia and primary amines with acyl chlorides

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Acid Anhydrides Flashcards

chemical test derivative for acid anhydride - many acid anhydrides are converted by water to their corresponding carboxylic acids although large aliphatic anhydrides and aromatic anhydrides are not readily hydrolyzed with water corresponding carboxylic acid is detected by addition of sodium bicarbonate = evolution of carbon dioxide

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REACTIONS OF CARBOXYLIC ACID DERIVATIVES WITH NUCLEOPHILES

21 8 REACTIONS OF CARBOXYLIC ACID DERIVATIVES WITH NUCLEOPHILES 1019 Reaction of Acid Chlorides with Carboxylate Salts Even though carboxylate salts are weak nucleophiles acid chlorides are reactive enough to react with carboxylate salts to give anhydrides This is a second general method for the synthesis of anhydrides Although the

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Caboxylic acid Derivatives

Ch21 Carboxylic acid Derivatives(landscape) docx Page 1 Carboxylic acid Derivatives Carboxylic acid derivatives are described as compounds that can be converted to carboxylic acids via simple acidic or basic hydrolysis The most important acid derivatives are esters amides and nitriles although acid halides and anhydrides are also derivatives (really activated forms of a carboxylic acid)

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Nomenclature preparation and properties of i Acid

Acid anhydrides are considered to be derived from carboxylic acids by the removal of a molecule of water from two molecules of acid So acid anhydrides can be prepared by heating carboxylic acid in the presence of P 2 O 5 in dehydrating agent Industrially acetic anhydride is prepared by heating acetic acid to 1073 K

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