[PDF] Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions





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Chapter 6 Amines and Amides

Learn the IUPAC system for naming amines and amides. inhibits cyclic adenosine monophosphate ... Amides are named by changing the -oic acid ending.



Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Amides are named by replacing the –ic acid or –oic acid ending with –amide or by rep- lacing the –carboxylic acid ending with –carboxamide. Cyclic amide 



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.



Carboxylic Acids A carbonyl with one OH attached is called a

Direct Acid to Amide Interconversion. An amide can also be formed directly from carboxylic acid by combining the two A cyclic amide is called a lactam.



Untitled

CYCLIC ACIDS ARE NAMED AFTER THE CYCLOALKANE SACTS ARE NAMED BY REPLACING THE ... AS A RESULT OF THIS STABILIZATION AMIDES ARE VERY WEAK BASES. CYCLIC ...



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Loudon Chapter 21 Review: Carboxylic Acid Derivatives

3 nov. 2021 Cyclic esters and amides are called lactones and lactams respectively. These groups do just the same chemistry as a normal ester or amide ...



U.S. Court of International Trade

8 juin 2016 when the terms and conditions of the rebate are known to the cus- ... function compounds of carbonic acid: Acyclic amides (including acyclic.



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13 mai 2016 State of the Art: Oxidations of Primary Secondary

Carboxylic Acid Derivatives: Nucleophilic Acyl

Substitution ReactionsSubstitution

Reactions

(Nitriles are treated as acid derivatives as they have similar reactivity.) Com p ounds containin g g rou p are called nitriles:pg gp • Simple open-chain nitriles are named by adding -nitrileas a suffix to the alkane

names, with the nitrile carbon numbered C1;• Nitriles can also be named as derivatives of carboxylic acids by replacing the

ic acidor -oic acidending with -onitrile, or by replacing the -carboxylic acidending with -carbonitriles;

• The nitrile carbon is attached to C1 carbon.

18-1

Naming Carboxylic Acid DerivativesAcid halidesare named by identifying first the acyl group and then the halide;

the acyl group name is derived from the carboxylic acid name by replacing the ic acid or the acid name by replacing the ic acid or the -carboxylic acidending with -ylor -carbonyl, respectively.O Cl pentanoyl chlorideS y mmetric anh y dridesandc y clic anh y dridesare named b y re p lacin g the word 18-2 yy yy yp g acidwithanhydride; unsymmetrical anhydridesare named by citing the two acid alphabetically and then addinganhydrides.

Naming Carboxylic Acid DerivativesEstersare named by first identifying the alkyl group attached to the oxygen and then the

carboxylic acid, with the -ic acidreplaced with-ate. A cyclic ester is called a lactone(the common name); the systematic name is oxa-2-cycloalkanone. -valerolactone (systematic: 5-methyloxa-2- cyclopentanone) -propiolactone (systematic: oxa-2-cyclobutanone)-butyrolactone

(systematic: oxa-2-cyclopentanone)Amidesare named by replacing the -ic acidor -oic acidending with -amide, or by rep-

lacing the -carboxylic acidending with -carboxamide. Cyclic amide are called lactams (the common name); the systematic name is aza-2-cycloalkanones. llt 18-3 -va l ero l ac t am (systematic: aza-2- cyclohexanone)

Spectroscopy of Carboxylic Acid Derivatives

18-4

Nucleophilic Acyl Substitution Reactions

Tetrahedron

intermediate

Greater resonance, shorter C- L bond

18-5

Factoids of Acid Derivatives

tthi f fCO s t re t c hi ng f requency o f C O

Two bands corresponding

Rotational activation

energy E a = 88 kJ mol -1 Two bands corresponding to symmetric and asymmetric stretching motions a

Greatly help

Acid derivatives are both basic and acidic

Greatly

help stabilize the protonated species

Relative reactivity:

electronic effectelectronic effect 18-6 Relative Reactivity of Carboxylic Acid Derivatives steric effect

Interconversion

diagram 18-7

Acyl Substitution Reactions of Acid Halides

A s acid halides are most reactive among all acid derivatives, all these reaction could happen with the acid halides.

Recall preparation:Recall

preparation: 18-8

Acyl Substitution Reactions of Acid Halides

Hydrolysis:

Base is needed to neutralized the HCl formed.

Alcoholysis:

1 o alcohol (l hi d d d

Alcoholysis:

(l ess hi n d ere d an d more reactive) Ai li 2 o alcohol (more hindered and less 1 o and 2 o amines can be used, but not 3 o amines A m i no l ys i s: (more hindered and less reactive) Two equivalents of amine are used due to the HCl formation. 18-9

Reactions of Acid Halides

When the amine isWhen

the amine is valuable, 1 eq. of NaOH can be added in addition to 1 eq. of the amine.

Reduction: hydride

substitution-addition

The modified LAH reacts

with acid chloride faster than

Modified

LAH: with the resulting aldehyde.

Reaction of

diorganocopper

With G i d

diorganocopper reagent happens only with acid halides; but not with carboxylic id t id With G r i gnar d

Reagent:

18-10 ac id s, es t ers, am id es, or acid anhydrides.

With Gilman

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