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

Fischer Esterification is also known as acid-catalyzed esterification. Why is it so important? Because we convert an OH group to an OR group. 

Concept #1: General Reaction

Concept #2: General Mechanism


BTW if you notice that when drawing the first resonance structure in red there is an arrow that looks off, don't be alarmed! The arrow should go the opposite direction [from the double bond to the +OH group]

Additional Problems
Which of the following is (are) tetrahedral intermediate(s) in the acid catalyzed esterification of benzoic acid with ethanol?
In the acid catalyzed esterification of compound  1, several possible intermediates are shown. Indicate the order in which these intermediates would appear during the conversion of 1 into 2. a) 1 → I → IV → V→ III → 2 b) 1 → II → IV → 2 c) 1 → III → IV → I→ V → 2 d) 1 → III → I → V→ IV → 2 e) 1 → I → III → IV → 2  
Draw a reasonable mechanism for the reaction below.
Provide a detailed reaction mechanism for the following transformation. This is an intramolecular version of what type of reaction?
Provide a detailed mechanism for the esterification reaction below.
What is the best choice of reagent(s) to perform the following transformation? a CH3OH, H2SO4 b CH3I, H2SO4 c NaOCH3 d CH3Li e CH3MgBr
Draw the organic product(s) for the following reaction. Indicate stereochemistry where appropriate. Assume an aqueous workup, when necessary. A reasonable answer may be “ No Reaction.”
Predict the product. NOTE: the product has 6 oxygens
Draw reasonable mechanisms for the reaction below.
Provide an electron push mechanism for the following transformation. Be sure you use the correct arrow formalism and correct non-zero formal charges.
Predict the product(s) for each of the following reaction. When appropriate, label them major and minor.
Draw the structural formula of the reactant(s), reagents(s) or the major organic product(s) in the boxes 
Predict the product(s) for the following reaction. When appropriate, label them major and minor. 
Draw the structure of the major organic product(s) of the reaction. 
What product would you expect to obtain from the following reaction?
Draw the structures of the major organic products of the following reaction.