Ch. 20 - Carboxylic Acid Derivatives: NAS WorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Hydroxycarboxylic acids and aminocarboxylic acids can be made to cyclize, forming lactones and lactams, respectively. 

Concept #1: Lactones and Lactams

Note: If you're thinking that the β-lactam is missing a hydrogen on the N, you are right! 

Example #1: Cyclization Reaction

Concept #2: Cyclic Anhydrides and Imides

Additional Problems
Shown below is a penicillin derivative meticillin (formerly methicillin). Which of the shown regions of this molecule reacts with the bacterial enzyme transpeptidase, which in turn inhibits cell wall synthesis and kills the cell?
Provide a mechanism for the following reaction.   
Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.
Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.
Predict the major product(s) for the reaction below. 
Complete the following reaction with the correct structure of the product. Don’t forget to specify the stereochemistry.
Propose two mechanisms for the following reaction. 
Which is a γ lactam?
Choose the reaction coordinate that best describes the following reaction.
Predict the product for the following reaction
Provide the mechanism for the following reaction. 
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product, if stereoisomers are produced in the reaction be sure to indicate the relationship between them. Draw the answer in skeletal form.
Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.
Provide the missing reagents to complete the following transformation.
Draw a reasonable mechanism for the reaction below. 
Provide a detailed mechanism for the following reaction. All arrows and structures of intermediates must be clearly indicated. 
Give a stepwise mechanism for the following lactone formation:
What is the product of the following reaction?
What is the product of the following reaction?
For the reaction below, draw the structure of the appropriate compound in the box provided. Indicate stereochemistry where it is pertinent.