Carboxylic Acids and Their Derivatives
reactions of carboxylic acids and will also discuss some common carboxylic acid derivatives in which the hydroxyl group of an acid is replaced by other
Chapter 21: Carboxylic Acid Derivatives
Class I carbonyl compounds are those that will react by acyl substitutions. They are all derivatives of carboxylic acids:.
REACTIONS OF CARBOXYLIC ACIDS & DERIVATIVES
Reactions of carboxylic acids and their derivatives (acyl halides anhydrides
Organic Chemistry II / CHEM 252 Chapter 18 – Carboxylic Acids and
compounds called acyl compounds or carboxylic acid derivatives The carboxylic acid portion follows and its name ends with -ate or -.
CARBOXY
Carboxylic Acids and Their Derivatives. 789 account of all of the structural effects as well as the possible reactions or inter-.
Chapter 12 Carboxylic Acids and Derivatives
(c) Comparison among the reactivity of carboxylic acid derivatives. 12.4 Reaction of carboxylic acids and their derivatives. (a) Acidity of carboxylic acids.
Chapter 5 Carboxylic Acids and Esters
Learn the major chemical reaction of carboxylic acids and esters and learn how to derivative of a carboxylic acid in which there is a.
Carboxylic acid Derivatives
Cyclic amides are known as Lactams. Lactams are produced from amino acids where the amino and the carboxylic acid groups react together to form an amide
Unit: 3 : Carboxylic Acid Derivatives
(b) Alcoholysis ( Conversion into esters). It involves the conversion of acid chloride into ester by reaction with alcohol and hence called as alcoholysis.
UNIT – I - CARBOXYLIC ACIDS AND THEIR DERIVATIVES
Hence their M.P. and B.P. are low as compared to those of the corresponding carboxylic acids. CHEMICAL REACTIONs a. Hydrolysis in presence of acid b. Hydrolysis
REACTIONS OF CARBOXYLIC ACIDS & DERIVATIVES - UAlberta
Reactions of carboxylic acids and their derivatives (acyl halides anhydrides esters amides) resemble those of ketones and aldehydes but replacement (substitution) of an electronegative group on the carbonyl is the common extra feature Most reactions follow a pattern: 1
Chapter 16: Carboxylic Acids Esters and Other Acid Derivatives
Carboxylic acids are easily by oxidation of primary alcohols and aldehydes When the oxidation process begins with an alcohol it is difficult to stop at the aldehyde stage of oxidation Oxidation of primary alcohol to carboxylic acid Chemical equations CH3CH2CH2OH ---> CH3CH2CHO ---> CH3CH2COOH
What is the empirical formula of carboxylic acid
12 4 Reaction of carboxylic acids and their derivatives (a) Acidity of carboxylic acids (b) Oxidation and reduction Oxidation Reduction (c) Grignard reaction (d) Interconversion among carboxylic acids and their derivatives Conversion from acid halides Conversion from acid anhydride Conversion from carboxylic acids and esters
Chem 215-216 HH W12 Notes Chapter 15: Carboxylic Acids and
Chapter 15: Carboxylic Acids and Their Derivatives and 21 3 B C/21 5 A “Acyl-Transfer Reactions” I Introduction R Z O an acyl group bonded to an electronegative atom (Z) RO O R R' R": alkyl alkenyl alkynyl or aryl group H Examples: R X OX = halogen RO O R S O R N O RO O R F O R Cl O R Br O R I O carboxylic acid R' R' R" R' R' O acid
Chapter 15: Carboxylic Acids and Their Derivatives and 213 B
IX Reactions of Carboxylic Acid Derivatives: (2) Reactions with Organometallic Reagents (ii) Reaction with carboxylic acids: Grignard reagents react to form carboxylate salts and the resulting salts do not undergo a further reaction with the Grignard reagents at room temperature
Searches related to reactions of carboxylic acids and their derivatives pdf filetype:pdf
Chapter 15: Carboxylic Acids and Their Derivatives and 21 3 B C/21 5 A “Acyl-Transfer Reactions” I Introduction R Z O an acyl group bonded to an electronegative atom (Z) RO O R R' R": alkyl alkenyl alkynyl or aryl group H Examples: R X OX = halogen RO O R S O R N O RO O R F O R Cl O R Br O R I O carboxylic acid R' R' R" R' R' O acid
What is the empirical formula for carboxylic acid?
- What is the empirical formula of carboxylic acid? The general formula for the carboxylic acids is C nH 2n+1COOH (where n is the number of carbon atoms in the molecule, minus 1). What is the empirical formula of copper oxide?
Why is carboxylic acid called weak acid?
- Unlike mineral acids, the carboxylic acids (of the form RCOOH) do not completely ionise. They partially ionise to give H+ and RCOO-. Therefore they are called weak acids. Methanol on oxidation in the presence of a strong oxidising agent like alkaline KMnO4 produces methanoic acid.
Why are esters considered derivatives of carboxylic acids?
- The properties of the amide functional group differ from those of the simple carbonyl group, NH 3, and amines. Esters and amides are considered to be derivatives of carboxylic acids because the OH in the carboxyl group is replaced with another group.
Chapter 21:Chapter 21:
Carboxylic Acid DerivativesCarboxylic Acid DerivativesCarboxylic Acid DerivativesCarboxylic Acid Derivatives
284?Class I carbonyl compounds are those that will react by acyl substitutions. They are all derivatives of carboxylic acids: RH O RR O cannot be replaced by a nucleophile 285
Class II
aldehydeketone R OH O ROR O RO O RX O RNH2 OO R carboxylic acidesteranhydrideacyl halides amidescompounds with groups that can be replaced by a nucleophileClass I
?Physical Properties (21-3) ?Boiling points increases with the strength of the dipolar interactions. 286?The large boiling points of nitriles, acids and amides is due to the strong dipolar forces that are found in these compounds.
287?Interconversion of Acid Derivatives(21-5)
Acid derivatives normally react by nucleophilic
acyl substitution. The general mechanism of this process is given below. Following this mechanism, it is possible to transform one acid derivative into another one. 288?The reactivity of acid derivatives can be correlated to the leaving group ability of the base that is expelled. The better the leaving group, the more reactive will be the acid derivative. Not surprising
that acid chloride are the most reactive derivatives. 289?This is the reason ketones and aldehydes will not react by acyl substitutions. The leaving group is either R -or H-, which are very basic, therefore poor leaving groups OO 290
RH poor leaving groups
?In theory, it is possible to go from one acid derivatives to another one. In practice, only the following reactions are normally used.
Rule: a more
Rule: a more
reactive intermediate can be converted into a less reactive one. 291Conversion of Acid Chloride to AnhydrideConversion of Acid Chloride to Anhydride 292
Conversion of Acid Chloride to EstersConversion of Acid Chloride to Esters 293
Conversion of Acid Chloride to AmidesConversion of Acid Chloride to Amides 294
Conversion of Anhydrides to EstersConversion of Anhydrides to Esters 295
Conversion of Anhydrides to AmidesConversion of Anhydrides to Amides 296
Practice QuestionsPractice Questions
?If you were starting with acetyl chloride, what nucleophile would you use to prepare the following compounds.
O O 297NHCH2CH3
O ?Write a detailed stepwise mechanism of the reaction taking place between acetyl chloride and water. 298Conversion of Esters to Amides Conversion of Esters to Amides ((AmmonolysisAmmonolysis)) 299
?In all of these reactions, the key feature was the basicity of the nucleophile and leaving group. If the nucleophile is more basic than the leaving group, the reaction will proceed. However, if the nucleophile is less basic than the leaving group, no reaction will occur. Hence, knowing pKa is important.
NH2 ONaClCl
O NaNH2 300this reaction will not proceed since Cl- is a weaker base than NH 2- Cl O
NaNH2NH2
O NaCl however this reaction is easy since the leaving group Cl -is a weaker base than NH 2- •Transesterification(21-6)This reaction is very similar to the hydrolysis
reaction (see 21-7). The only difference is that an alcohol is used in large excess instead of water.This results in the formation of a new ester, one
that has the structure of the alcohol that was used in excess. The reaction can be performed under basic or acidic conditions, the latter being more common.common. 301Mechanism of Mechanism of TransesterificationTransesterification 302
?Hydrolysis of Acid Derivatives(21-7)
This reaction is the reason all of these
compounds are considered acid derivatives...because they produce carboxylic acids upon hydrolysis. This reaction can be performed under acidic or basic conditions. Acid Chlorides/AnhydridesAcid Chlorides/AnhydridesThese two compounds are so reactive that the
hydrolysis can be performed under neutral conditions. 303Esters
Esters can be hydrolyzed under acidic or
basic conditions. Under basic conditions, the reaction is known as " saponification" 304?Under acidic conditions, the mechanism of hydrolysis is the reversed of the Fisher Esterification. H OCH3 OH+OH OCH3 OH H OH OCH3 OH H+ OCH3 O H2O 305
OH O B-H OH OCH3 OH+ HH+B- OH O
Amides
Amides also hydrolyze to acids
under basic or acidic conditions. 306Base Catalyzed Hydrolysis of AmidesBase Catalyzed Hydrolysis of Amides 307
Acid Catalyzed Hydrolysis of AmidesAcid Catalyzed Hydrolysis of Amides 308
Nitriles
Nitriles are considered acid derivatives
because they generate the corresponding acids under hydrolysis conditions.Reactions can be performed under acidic
or basic conditions. 309Base Catalyzed Hydrolysis of Base Catalyzed Hydrolysis of NitrilesNitriles 310
Practice QuestionPractice Question
?What product would be formed from the acid- catalyzed hydrolysis of the following esters? 311•Reduction(21-8)
Like other compounds bearing C=O functions,
acid derivatives can be reduced easily using reagents such as (LiAlH4). The majority of the
reductions of acid derivatives give the corresponding primary alcohols. Aldehydes and amines can also be generated. Esters(formation of 1o alcohol)Esters(formation of 1o alcohol) 312Mechanism of Ester ReductionMechanism of Ester Reduction 313
Acid Chlorides
They can be reduced to the
corresponding primary alcohols with LiAlH4. However, the use of a bulkier
reagent prevents the reduction to continue past the aldehyde product. 314Amides(formation of amines)
Amides are reduced to 1
o, 2oor 3oamines with LiAlH 4. 315Mechanism of Amide ReductionMechanism of Amide Reduction 316
Nitriles
In a similar reactions, nitriles can also be
reduced to the corresponding primary alcohols. 317?Reactions of Acids Derivatives with Grignards (21-9)
We have seen that esters and acid chlorides add
two equivalents of Grignard reagent to give tertiary alcohols. 318Nitriles
Nitriles also react with Grignard reagent
to give the corresponding imine. Under acidic conditions, imines are easily converted to the corresponding ketones (see Chapter 18-16) 319SummarySummary: Acid Chlorides (21: Acid Chlorides (21--10)10) 320
321
SummarySummary: Anhydrides (21: Anhydrides (21--11)11) 322
SummarySummary: Esters (21: Esters (21--12)12)
323SummarySummary: Amides (21: Amides (21--13)13)
324SummarySummary: : NitrilesNitriles (21(21--14)14)
325quotesdbs_dbs20.pdfusesText_26
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