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.


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: 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.




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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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ORGANIC - BROWN 8E CH. 17 - CARBOXYLIC...

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