Carboxyl group and esters

• What functional group characterizes carboxylic acids?

  • COOH
• How are carboxylic acids produced?

  From the oxidation of 1° alcohols under reflux
• What happens when carboxylic acids dissociate in solution?

  They form H+ ions and carboxylate ions

  
• What do carboxylic acids produce when they react with carbonates?

  A carboxylate salt, water, and CO2
• Why are small chain carboxylic acids soluble in water?

  They form hydrogen bonds with water molecules
• What do carboxylic acids react with to form esters?

  Alcohols in the presence of a strong acid catalyst

  
• What is the process called when carboxylic acids react with alcohols?

  Esterification

  
• How can you remember the esterification reaction process?

  • Remove -OH from the acid
  • Remove H from the alcohol
  • Combine acid and alcohol to form ester
• What are esters commonly used for?

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

  Glycerol and fatty acids
• What is biodiesel produced from?

  Vegetable oils and methanol
• What is ester hydrolysis?

  The reverse reaction to esterification
• What conditions produce a simple reverse reaction in ester hydrolysis?

  Acidic conditions

  
• What happens under alkaline conditions during ester hydrolysis?

  The carboxylic acid reacts to form a salt

  
• What is the process of forming a salt from a carboxylic acid called?

  Saponification

  
• What are the three main derivatives of carboxylic acids?

  • Acid Anhydrides
  • Acyl Chlorides
  • Amides
• How are acid anhydrides formed?

  By removing water from two carboxylic acids
• Why do acyl chlorides react violently?

  Due to the very polar -COCl group
• What do amides react to form?

  1. substituted amides
• What type of reactions do carboxylic acid derivatives undergo?

  • Nucleophilic addition-elimination reactions
  • Addition of a nucleophile
  • Elimination of a product under aqueous conditions
• What do acyl chlorides react with to produce a carboxylic acid?

  Water
• What do acyl chlorides react with to produce an ester?

  Alcohol
• What do acyl chlorides react with to produce an amide?

  Ammonia

  
• What do acyl chlorides react with to produce an N-substituted amide?

  Amines

  
• What is aspirin produced from?

  Salicylic acid and ethanoic anhydride

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

  It is expensive and produces harmful HCl fumes
• Why is ethanoic anhydride preferred in industry for aspirin production?

  It is much safer for industrial use
• How are carboxylic acids named?

  By finding the longest carbon chain
• Where is the carboxyl group located in carboxylic acids?

  At the end of the molecule
• What is the name of the carboxylic acid with two carbons?

  Ethanoic acid
• How is the carboxyl group numbered in a carbon chain?

  Always as carbon one
• What type of acid is a carboxylic acid?

  Weak acid
• What is the general reaction of acids with carbonates?

  Acid + carbonate → salt + water + CO₂
• What do carboxylic acids produce when they react with carbonates?

  Carbon dioxide
• What is the equilibrium position for weak acids?

  It lies to the left
• What is produced when ethanoic acid reacts with sodium carbonate?

  Sodium ethanoate, water, and CO₂
• What is the role of sulfuric acid in esterification?

  It acts as a catalyst
• What is formed when a carboxylic acid reacts with an alcohol?

  An ester
• What is the structure of an acid anhydride?

  Like a carboxylic acid without an OH
• How are esters named?

  From the alcohol and carboxylic acid