Carboxylic acids and esters

• What functional group is characteristic of carboxylic acids?

  • COOH
• How are carboxylic acids produced?

  From the oxidation of primary alcohols under reflux
• Why are small chain carboxylic acids soluble in water?

  They can form hydrogen bonds with water molecules
• What is the process called when carboxylic acids react with alcohols to form esters?

  Esterification

  
• What is a method to remember the esterification reaction?

  Remove the -OH from the acid and the hydrogen from the alcohol to make water, then combine them
• What are esters commonly used for?

  Food flavorings and perfumes
• What are triglyceride esters derived from?

  Vegetable oils and fats from glycerol
• What is biodiesel produced from?

  Vegetable oils and methanol
• What is ester hydrolysis?

  The reverse reaction of esterification, converting esters back into alcohols and carboxylic acids

  
• What happens under acidic conditions during ester hydrolysis?

  It produces a simple reverse reaction back to an alcohol and a carboxylic acid

  
• What occurs under alkaline conditions during ester hydrolysis?

  The carboxylic acid produced reacts further with the base to form a salt

  
• What is the process of producing a salt from ester hydrolysis called?

  Saponification
• Why are salts produced from saponification used as soaps?

  They have hydrophilic and hydrophobic properties
• What are the three main derivatives of carboxylic acids?

  Acid anhydrides, acyl chlorides, and amides
• How are acid anhydrides formed?

  When water is removed from two carboxylic acids
• Why do acyl chlorides react violently?

  Due to the very polar -COCl group
• What type of reactions do carboxylic acid derivatives undergo?

  Nucleophilic addition-elimination reactions
• What do acyl chlorides produce when they react with water?

  Carboxylic acid
• What is aspirin produced from?

  Salicylic acid and ethanoic anhydride

  
• Why is ethanoyl chloride not commonly used in industry for producing aspirin?

  It is expensive and produces harmful HCl fumes
• What are the key properties of carboxylic acids and esters?

  • Carboxylic acids contain the -COOH functional group.
  • They are weak acids that dissociate in solution.
  • Esters are formed from carboxylic acids and alcohols.
  • Esters have low boiling points and are sweet-smelling.
• What are the steps involved in esterification?

  1. Combine carboxylic acid and alcohol.
  2. Remove -OH from the acid and H from the alcohol to form water.
  3. Stick the acid and alcohol together to form an ester.
• What are the conditions for hydrolysis of esters?

  • Acidic conditions: Produces alcohol and carboxylic acid.
  • Alkaline conditions: Produces salt and alcohol.

  
• What are the uses of triglyceride esters?

  • Used in food products.
  • Used in biodiesel production.
  • Serve as a source of energy.
• What are the reactions of acyl chlorides with other compounds?

  • Water: Produces carboxylic acid.
  • Alcohol: Produces ester.
  • Ammonia: Produces amide.
  • Amines: Produces N-substituted amide.

  
• What are the characteristics of nucleophilic addition-elimination reactions?

  • Involves the addition of a nucleophile.
  • Leads to the elimination of a product.
  • Occurs under aqueous conditions.