Questions and Answers
What is a key feature of the molecular structure of an acid anhydride?
Which process is involved in the synthesis of a carboxylic acid anhydride?
How are amides named when they are substituted with alkyl groups on the nitrogen?
Which statement accurately describes the role of the base in the formation of acid anhydrides?
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What illustrates the general method for preparing amides?
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Which of the following reagents is NOT commonly used for the oxidation of primary alcohols to synthesize carboxylic acids?
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What is the primary feature that distinguishes acid chlorides from other carboxylic acid derivatives?
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In the mechanism of acid chloride formation using SOCl2, what role does the carboxylic acid play?
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Which statement regarding Fischer esterification is correct?
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What happens to the byproducts produced during the formation of acid chlorides when using SOCl2?
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Study Notes
Carboxylic Acid Derivatives
- Common derivatives include acyl halides, acid anhydrides, esters, and amides.
- Primary alcohols oxidize to form carboxylic acids using strong oxidizing agents like chromic acid, potassium permanganate, or nitric acid.
Acid Halides
- Acid chlorides are formed when carboxylic acids react with thionyl chloride, phosphorus trichloride, or phosphorus pentachloride.
- Acid chlorides are the most reactive carboxylic acid derivatives.
- The formation mechanism involves an electrophilic attack by the oxygen of the carboxylic acid on sulfur, resulting in the production of HCl and irreversible products (SO2 and HCl).
Esters (RCOOR')
- Formed when carboxylic acids react with alcohols.
- Long alkyl chain esters are found in fats and oils; small chain esters have fruity odors and are used in fragrances.
- Fischer esterification is the acid-catalyzed reaction producing esters.
Acid Anhydrides
- Contains two acyl groups bonded to the same oxygen.
- Formed when a carboxylic acid reacts with an acid chloride in the presence of a base.
- Synthesis follows an addition-elimination mechanism, involving chloride ion as the leaving group.
Amides
- Composed of carbonyl groups attached to nitrogen atoms.
- Naming involves changing the carboxylic acid suffixed to "-oic" to "-amide”.
- Prepared by reacting acid chlorides with ammonia or amines.
Reactivity Order of Carboxylic Acid Derivatives
- Acid chlorides are the most reactive due to electron-withdrawing effects.
- Acid anhydrides follow closely in reactivity.
- Reactivity decreases with thioesters, esters, and amides being the least reactive.
- Carboxylate ions are least reactive because of their negative charge, which repels nucleophiles.
Organic Reactions of Carboxylic Acids
- Decarboxylation: Loss of CO2 from carboxylic acids, producing halocompounds or hydrocarbons.
- Example: Method using sodalime (NaOH and CaO mixture).
Acidity of Carboxylic Acids
- Carboxylic acids are weak acids, dissociating in water to produce hydronium and carboxylate ions.
- A 1.0 M acetic acid solution is about 0.5% dissociated in water.
Chemical Properties
- All carboxylic acid derivatives can be hydrolyzed by water to regenerate the parent acid and respective byproducts.
Excretion and Drug Metabolism
- Acid derivatives used in drugs undergo phase I metabolism (hydrolysis) in the liver and phase II metabolism (water solubility) for renal excretion.
Medicinal Uses
- Carbonyl groups are common in natural products (prostaglandins, lipids, hormones).
- Important medicinal compounds include aspirin (acetylsalicylic acid), acetaminophen, and ampicillin.
Sulphonic Acids and Their Derivatives
- Sulphonic acids (RSO3H) are stronger acids than carboxylic acids due to resonance stabilization.
- Derivatives include chlorides, esters, and amides.
- Important sulphonamide drugs in pharmacy include sulphamethoxazole and sulphadoxine, used for antibacterial and antimalarial treatments.
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Description
Test your knowledge on carboxylic acid derivatives, including acyl halides, acid anhydrides, esters, and amides. Explore the synthesis and reactions involving strong oxidizing agents like chromic acid and potassium permanganate. Perfect for organic chemistry enthusiasts!
