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 ...
The Chemistry of Carboxylic Acid Derivatives
Esters are named as derivatives of their parent carboxylic acids by applying Cyclic amides are called lactams and the common nomenclature of the simple ...
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.
C?–H Oxidations of Amines to Amides: Expanding Mechanistic
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 alkanenames, 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.
18-1Naming 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
18-4Nucleophilic Acyl Substitution Reactions
Tetrahedron
intermediateGreater resonance, shorter C- L bond
18-5Factoids of Acid Derivatives
tthi f fCO s t re t c hi ng f requency o f C OTwo bands corresponding
Rotational activation
energy E a = 88 kJ mol -1 Two bands corresponding to symmetric and asymmetric stretching motions aGreatly help
Acid derivatives are both basic and acidic
Greatly
help stabilize the protonated speciesRelative reactivity:
electronic effectelectronic effect 18-6 Relative Reactivity of Carboxylic Acid Derivatives steric effectInterconversion
diagram 18-7Acyl 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: 18-8Acyl Substitution Reactions of Acid Halides
Hydrolysis:
Base is needed to neutralized the HCl formed.
Alcoholysis:
1 o alcohol (l hi d d dAlcoholysis:
(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. 18-9Reactions 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-additionThe modified LAH reacts
with acid chloride faster thanModified
LAH: with the resulting aldehyde.Reaction of
diorganocopperWith G i d
diorganocopper reagent happens only with acid halides; but not with carboxylic id t id With G r i gnar dReagent:
18-10 ac id s, es t ers, am id es, or acid anhydrides.With Gilman
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