Carboxylic Acids and Their Derivatives

1
Chapter 17

• Carboxylic Acids and Their Derivatives

2
Carboxylic Acids and Their Derivatives

• Carboxylic Acids, Esters and Amides

3
Carboxylic Acids and Their Derivatives

• Carboxylic Acids, Esters and Amides are polar
  species
• Evaluate each of the derivatives and answer the
  following questions.
• ? Higher or lower boiling point than the similar
  alkane ?
• ? Higher or lower boiling point than the similar
  alcohol ?

4
Carboxylic Acids and Their Derivatives

• Carboxylic acids, Esters and Amides undergo
  carbonyl group substitution reactions (also
  referred to as acyl transfer reactions)
• Acyl group is the portion of the carboxylic acid
  that does not change

5
Carboxylic Acids and Their Derivatives

• Carboxylic Acid
• Polar molecule
• Can form hydrogen bonds between acids through the
  hydroxide group
• R group of 4 carbons or less are water soluble
• Have an acidic hydrogen

6
Carboxylic Acids and Their Derivatives

• IUPAC Naming of Carboxylic Acids
• Name the alkane
• Replace the e with oic acid
• If acid contains additional substituents begin
  numbering the Cs with the acid C.

7
Carboxylic Acids and Their Derivatives

• Common names of acids used more often than IUPAC

8
Carboxylic Acids and Their Derivatives

• The acyl group that remains after losing the OH
  group of the carboxylic acid is named by
  replacing the ic of the acid with oyl
• Exception acetyl group

9
Carboxylic Acids and Their Derivatives

• Dicarboxylic Acids
• IUPAC naming
• Name the alkane
• Replace the e with dioic acid
• Simple dicarboxylic acids have common names which
  we will encounter when we discuss biochemical
  energy and the citric cycle in section 21.8.

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Carboxylic Acids and Their Derivatives

• Unsaturated acids (contain a double bond)
• IUPAC naming
• Name the alkene
• Replace ene with enoic acid

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Carboxylic Acids and Their Derivatives

• Esters
• Created by reacting an carboxylic acid with an
  alcohol
• Are polar molecules but can not hydrogen bond
  with one another
• ? B.P. higher or lower than related acid ?
• ? B.P. higher or lower than related alcohol ?
• ? B.P. higher or lower than related alkane ?
• Pleasant odors responsible for natural
  fragrances

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Carboxylic Acids and Their Derivatives

• Names of Esters
• Consist of 2 parts
• 1st part is the name of the alkyl group attached
  to the O of the original alcohol
• 2nd part is the name of the parent acid
• Drop ic acid and replace with ate

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Carboxylic Acids and Their Derivatives

• Amides
• Formed by combining a carboxylic acid with an
  amine
• Unsubstituted Amides form 3 strong H-bonds
• ? B.P. higher or lower than related acid ?
• ? B.P. higher or lower than related alcohol ?
• ? B.P. higher or lower than related alkane ?
• ? B.P. higher or lower than related ester?
• Monosubstituted amide can form 2 H-bonds
• Disubstituted amide can form no H-bonds
• Amides are not basic like an amine

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Carboxylic Acids and Their Derivatives

• Naming Amides
• Named by replacing oic acid or ic acid of the
  carboxylic acid with amide
• If the N of the amide has substituents
• Specify the alkyl group and then identify the
  amide
• The alkyl groups are preceded by the letter N-

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Some Common Carboxylic Acids

• Read Section 17.2

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Acidity of Carboxylic Acids

• Carboxylic acids are weak acids in aqueous
  solutions
• The carboxylic acid donate the H of the COOH
  group to form a carboxylate ion COO-
• To name a carboxylate
• Name the acid
• Replace ic acid or oic acid with ate

17
Aspirin and Other Over-the-Counter Carboxyic Acid
Derivatives

• Read Section 17.5

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Hydrolysis of Esters and Amides

• Hydrolysis (mentioned in 16.7) involves breaking
  bonds and adding H- and an OH where the bonds
  were broken
• Hydrolysis of Esters and Amides allow for the
  reformation of the parent carboxylic acid

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Hydrolysis of Esters and Amides

• 2 methods to perform Hydrolysis of Esters
• React the ester with water in the presence of a
  strong acid catalyst
• React the ester with a strong base
  (saponification)

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Hydrolysis of Esters and Amides
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Hydrolysis of Esters and Amides

• Hydrolysis of Amides
• Due to the stability of amides, hydrolysis
  requires that the amide, in the presence of an
  acid or base, be heated

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Polyamides and Polyesters

• Polymers result when two or more compounds link
  together to form long chains.
• Polyamides result from the reaction of a diamine
  with a diacid
• Nylon 66
• Proteins

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Polyamides and Polyesters

• Polyesters result from the reaction of a diacid
  with a diol

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Phosphoric Acid Derivatives

• Phosphoric Acid reacts similarly to a carboxylic
  acid to form esters

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Phosphoric Acid Derivatives

• Phosphate monoester and phosphate diesters still
  contain an acidic hydrogen
• In neutral or basic solutions (most body fluids
  are), exist in the ion form
• Ex glyceraldehyde monophosphate an
  intermediate in the metabolism of glucose

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Phosphoric Acid Derivatives

• Two phosphate groups can react together through
  the loss of water to form an phosphoric anhydride
  phosphorylation (transfer of a phosphate group)

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Phosphoric Acid Derivatives

• Phosphoric acid, like a carboxylic acid, can
  react with an alcohol to form an ester
  phosphate ester

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Phosphoric Acid Derivatives

• One common reaction of phosphoryl groups that
  occur is the transformation of ATP to ADP in the
  production of energy

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Homework

• 17.1, 17.2, 17.4, 17.5, 17.6, 17.7, 17.8, 17.9,
  17.10, 17.11, 17.12, 17.14, 17.15, 17.17, 17.18,
  17.19, 17.20, 17.23, 17.24, 17.26, 17.27, 17.28,
  17.29, 17.33, 17.34, 17.37, 17.38, 17.40, 17.42,
  17.43, 17.44, 17.46, 17.47, 17.48, 17.49, 17.50,
  17.52, 17.53, 17.54, 17.56, 17.57, 17.58, 17.59,
  17.60, 17.62, 17.63, 17.64, 17.65, 17.66, 17.68,
  17.70, 17.72, 17.86