CH. 20 - CARBOXYLIC ACID DERIVATIVES: NASlightcat-files.s3. COOH DERIVATIVES AND NUCLEOPHILIC ACYL...

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CH. 20 - CARBOXYLIC ACID DERIVATIVES: NAS

CONCEPT: COOH DERIVATIVES AND NUCLEOPHILIC ACYL SUBSTITUTION
Carboxylic acid derivatives are defined as any carbonyl with a single electronegative group (-Z) in the -position.
These follow unique nucleophilic mechanism due to the presence of a leaving group, called NAS.
By definition, they can ALL be hydrolyzed to a carboxylic acid using water with acid or base.
Nitriles also fall into this category due to their ability to be hydrolyzed
= -Cl, -COOR
-OR, -OH, - NH3
General Carbonyl Mechanisms:
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CONCEPT: CARBOXYLIC ACID NOMENCLATURE
IUPAC: Replace alkane -e with ________________________
Substituents are located using ____________
Common: Memorize the first 5 common names
Substituents are located using _____________
Negative anions (deprotonated) are named using the suffix _____________
EXAMPLE: Give both the correct IUPAC and common name for the following molecule.
( ) Formic Acid
( ) Acetic Acid
( ) Propionic Acid
( ) Butyric Acid
( ) Valeric Acid
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PRACTICE: Provide the IUPAC name for the following compound.
OH
Br O
OH
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CONCEPT: CARBOXYLIC ACID NOMENCLATURE
Diacids:
Memorize the first 3 common names
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PRACTICE: Provide the common name for the following compound.
HO
O
O
OH
O
O
OH
O
HO
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CONCEPT: ESTER NOMENCLATURE
The word ester is not found in ester nomenclature, making these difficult to recognize.
Name as an ________________ + ___________________________
EXAMPLE: Correctly name the following structure.
EXAMPLE: Correctly draw the following molecule.
Isopropyl formate
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CONCEPT: NITRILE NOMENCLATURE
Add suffix _________________ to the alkane name
Do not drop the e
Substituents are located using _______
2-amino-4-bromohexanenitrile
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CONCEPT: ACID CHLORIDE NOMENCLATURE
Common: Replace ic acid with the suffix -yl chloride
IUPAC: Replace e with the suffix -oyl chloride
EXAMPLE: Provide both the correct IUPAC and common name for the following molecule.
-ethylvaleryl chloride
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CONCEPT: ANHYDRIDE NOMENCLATURE
Alphabetize acids, then replace the word acid with ___________________
If you have two identical R groups, name as alkynoic anhydride
EXAMPLE: Provide both the correct name for the following molecule.
Formic anhydride
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CONCEPT: AMIDE NOMENCLATURE
Replace e with the suffix _______________
R groups on the nitrogen are named as substituents on the
--N or N, N positions
N, N-dibenzylacetamide
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CONCEPT: NUCLEOPHILIC ACYL SUBSTITUTION THE THREE RULES
Most of the formulas governing the conversion of carboxylic acid derivatives can be simplified into the following 3 Rules:
RULE #1 The general reactions for these conversions are as follows:
RULE #2 More reactive acyl compounds can be easily _______________________ into less reactive ones.
The reactivity of carbonyls toward NAS depends upon the strength of the __________________________
RULE #3 The Carboxylic Acid Conversions
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PRACTICE: Determine the major product for the following reaction.
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CONCEPT: SPECIFIC CARBOXYLIC ACID CONVERSIONS
Synthesis of Acid Chloride:
Synthesis of Amides:
Dehydration of Amides:
Hydrolysis of Nitriles:
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CONCEPT: FISCHER ESTERIFICATION MECHANISM
Also known as acid-catalyzed esterification, this is one of the more important mechanisms in this course.
General Reaction:
Mechanism:
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CONCEPT: FISCHER ESTERIFICATION MECHANISM
Also known as acid-catalyzed esterification, this is one of the more important mechanisms in this course.
General Reaction:
Mechanism:
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CONCEPT: ACID-CATALYZED ESTER HYDROLYSIS MECHANISM
The exact reverse of Fischer esterification.
General Reaction:
Mechanism:
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CONCEPT: BASE-CATALYZED ESTER HYDROLYSIS MECHANISM
Also known as saponification, this is one of the more important mechanisms in this course.
General Reaction:
Mechanism:
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CONCEPT: BASE-CATALYZED TRANSESTERIFICATION MECHANISM
Occurs when an ester is exposed to an alkoxide base with a dissimilar alkyl group.
Can be avoided by only exposing esters to alkoxides with the same R group as the ester
General Reaction:
Mechanism:
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CONCEPT: LACTONES, LACTAMS AND CYCLIZATION REACTIONS
Hydroxycarboxylic acids and aminocarboxylic acids can be made to cyclize, forming lactones and lactams, respectively.
5 and 6-membered rings can cyclize spontaneously
Lactones and Lactams:
EXAMPLE: Provide the correct structure for the following cyclization reaction and name the new functional group.
Formation of cyclic anhydrides and imides:
Cyclic Anhydrides and Imines
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CONCEPT: CARBONATION OF GRIGNARD REAGENTS
Grignard reagents can react with dry ice (frozen CO2 gas) to create carboxylic acids
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1. Br2 , hv2. Mg, ether
3. CO24. H3O+ workup
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CONCEPT: DECARBOXYLATION
-carbonyl carboxylic acids easily decarboxylate when heated, producing CO2 gas.
Mechanism:
EXAMPLE: Predict the correct structure for the final product.
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PRACTICE: Provide the mechanism for the following reaction.
O
OH
O O
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PRACTICE: Which carbonyl group will undergo decarboxylation most readily?
HOOC
C
C
C
O
OHO
O OHO
OH
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CH. 20 - CARBOXYLIC ACID DERIVATIVES: NASlightcat-files.s3. COOH DERIVATIVES AND NUCLEOPHILIC ACYL...

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