ORGANIC - BROWN 8E CH. 17 - CARBOXYLIC...
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ORGANIC - BROWN 8E
CH. 17 - CARBOXYLIC ACIDS
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.
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.
PRACTICE: Provide the IUPAC name for the following compound.
HO
O
O
OH
O
O
OH
O
HO
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CONCEPT: REDUCTION
□ Reducing agents are used to reduce molecules
● These reagents add hydrogens across π-bonds. Unsaturated hydrocarbons and carbonyls can be reduced.
General Mechanism: Nucleophilic addition of hydrogen
□ Reducing agents add to ALL π-bonds present. Multiple equivalents of hydrogen will react if possible.
● LiAlH4 is a strong reducing agent. It is able to reduce ANY carbonyl compound into alcohol
EXAMPLE: Draw the products of the following molecules reacted with LiAlH4
□ NaBH4 is a weak reducing agent. It can only add ____ equivalent of hydrogen and can only reduce CHO and ketones
EXAMPLE: Draw the products of the following molecules reacted with NaBH4
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PRACTICE: Predict the product of the following reactions
a.
b.
c.
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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: COOH DERIVATIVES AND NUCLEOPHILIC ACYL SUBSTITUTION
Carboxylic acid derivatives are defined as any carbonyl with a single electronegative group (-Z) in the α-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: 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.
PRACTICE: Determine the major product for the following reaction.
PRACTICE: Determine the major product for the following reaction.
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: DECARBOXYLATION
β-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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