Chapter 25 – Review

25.1 Carboxylic Acids – Structure and Naming

1. Give IUPAC names for the following substances:

   1. 

      Check answer^[1]

   2. Check answer^[2]
   3. Check answer^[3]

   4. 

      Check answer^[4]

   5. 

      Check answer^[5]

   6. 

      Check answer^[6]

   7. Check answer^[7]
2. Draw structures corresponding to the following names:
   1. 2,2-dimethylpropanoic acid Check answer^[8]
   2. 2,3-difluorobutanic acid Check answer^[9]
   3. 4,4-dimethylpentanoic acid Check answer^[10]
   4. Phenyl benzoate Check answer^[11]
   5. 2,4-Dimethylpentanoyl chloride Check answer^[12]

25.2 Physical Properties of Carboxylic Acids

1. Fatty acids are carboxylic acids that have long hydrocarbon chains attached to a carboxylate group. How does a saturated fatty acid differ from an unsaturated fatty acid? How are they similar? Check answer^[13]
2. What carboxylic acid is responsible for the pain of an ant sting? Check answer^[14]
3. What carboxylic acid is found in vinegar? Check answer^[15]

25.3 Formation and Reactions of Carboxylic Acids

1. Write the balance chemical equation for the dissociation of propanoic acid in water. Check answer^[16]
2. Write the balanced equations for each of the following reactions;
   1. ethanol reacts with propionic acid
   2. benzoic acid, C₆H₅CO₂H, is added to a solution of sodium hydroxide

25.4 Chemical Properties of Carboxylic Acids – Ionization and Neutralization

1. Write the balanced chemical equation for the neutralization of propanoic acid with sodium hydroxide. Check answer^[17]
2. Write the balanced chemical equation for the reaction of each of the following carboxylic acids with NaOH:
   1. formic acid Check answer^[18]
   2. 3-chloropropanoic acid Check answer^[19]

25.5 Esters – Structure, Properties and Naming

1. Draw the condensed structural formula for the ester formed when each of the following reacts with methyl alcohol:
   1. acetic acid Check answer^[20]
   2. pentanoic acid Check answer^[21]
2. Write the IUPAC and common names, if any, for each of the following:
   Check answer^[22]

25.6 Reactions of Esters

1. How do acidic hydrolysis and basic hydrolysis of an ester differ in terms of products obtained? Check answer^[23] And the extent of reaction? Check answer^[24]
2. An ester that has the smell of pineapple can be synthesized from butanoic acid and methanol. Write the balanced chemical equation for the formation of this ester. Check answer^[25]
3. Write an equation for the acidic hydrolysis of ethyl butyrate (CH₃CH₂CH₂COOCH₂CH₃) and name the products. Check answer ^[26]
4. Write an equation for the hydrolysis of methyl benzoate in a potassium hydroxide solution. Check answer^[27]

Attribution & References

Except where otherwise noted, this page (including images in solutions) is adapted by Caryn Fahey from:

• “Naming Carboxylic Acids Derivatives” In Organic Chemistry by John McMurray, CC BY-NC-SA 4.0.  Access for free at Organic Chemistry (OpenStax)
• “18.3 Aldehydes, Ketones, Carboxylic Acids, and Esters” In General Chemistry 1 & 2 by Rice University, a derivative of Chemistry (Open Stax) by Paul Flowers, Klaus Theopold, Richard Langley & William R. Robinson and is licensed under CC BY 4.0. ​Access for free at Chemistry (OpenStax)
• Images that are not marked otherwise are adapted from course materials by Caryn Fahey and JR van Haarlem
• Images in solutions are from the original source, except:
  • 25.6 Question 3, 4: Intro Chem: GOB (V. 1.0)., CC BY-NC-SA 3.0