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

It's time to learn about The 3 Rules for Nucleophilic Acyl Substitution. Are you ready?

Concept #1: NAS - The Three Rules

RULE 1: General Reactions

RULE 2: More reactive acyl compounds can be easily converted into less reactive ones. 

RULE 3: Carboxylic Acid Conversions

Practice: Determine the major product for the following reaction.

Practice: Determine the major product for the following reaction. 

Practice: Determine the major product for the following reaction. 

Practice: Determine the major product for the following reaction. 

Additional Problems
What are the product(s) formed from the following reaction? 
Consider the formation of an amide from an ester.  An estimate of the overall enthalpy of this transformation using the bond dissociation energies given below is  1) 13 kcal/mol     2) – 4 kcal/mol     3) – 17 kcal/mol 4) 7 kcal/mol    5) –11 kcal/mol Bond dissociation energies (kcal/mol)  C–H                                      99 C–O                                      79 C–C                                      85 C–N                                      66 R2N–H                                 92 C=O                                    175 C=N                                    145 RO–H                                 109
Choose the reaction coordinate that best describes the following reaction.
Predict the products and indicate the relative stereochemistry for the following transformations. When necessary indicate the major product.
What is the final principal organic product from the following transformation?
Show the product(s) for the acid catalyzed reaction between formic acid and 1-pentanol. 
Predict the product(s) formed in the following reaction.  
Draw the organic product(s) of the following reaction. Indicate stereochemistry where appropriate. A reasonable answer may be “ No Reaction.”
Rank in order of decreasing reactivity in toward nucleophilic addition-elimination.
Determine the necessary reagent and provide the mechanism for the reaction below.
Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 
What is the result of treating benzoyl chloride with aniline followed by LiAlH 4 then water? a) PhNHCH2Ph (Ph = phenyl) b) Diphenylamine c) Dibenzylamine d) N-Phenylbenzamide e) None of the above
Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 
Which reaction is the  least favorable (lowest Keq)?
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.”
Which of these reactions would produce this product?
Predict the product for the following reaction
Which would be hydrolyzed most slowly with aqueous NaOH?
Using your knowledge of base strengths, predict which of these reactions would be most likely to occur.  
What product would you isolate from these reactants?
Which set of products is obtained from this acid hydrolysis?
Predict the product formed from the reaction given below:
What are the products of this reaction?
What is the product of this reaction?
Arrange the following compounds so that reactivity towards aqueous potassium hydroxide increases from left to right.
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 product for the following reaction. 
Draw the major product(s) for the following reaction. Assume the nucleophile is in excess. If there will be no reaction, write NR.
Give step by step mechanism for the following transformation:
What is the product of the following reaction?
What is the product of the following reaction?
Predict the major product for the reaction paying, attention to the regio- and stereochemistry where necessary.
Draw the structural formula of the reactant(s), reagents(s) or the major organic product(s) in the boxes 
Show your understanding of the following reaction by showing the mechanism and predicting the products.
Which reaction would not proceed in good yield as written?
Predict the product(s) in the following reaction. If more than one product is possible, then indicate the major product.
Give the major organic product formed when the compound shown below undergoes a reaction with an excess of NH3
The product of the following reaction is: 
Draw the final organic product of the following reaction.
Draw the products of the following reaction.
Draw the product(s) of the following reaction
What is the major product from the following reaction? 
What are the products of the following reaction? Draw the molecules on the canvas by choosing buttons from the Tools (for bonds and char choosing the appropriate toolbar buttons and clicking on an atom.
Predict the product for the following reaction.
Draw the major products formed in the following reaction involving an acid anhydride dissolved in alcohol.
Complete the following reaction by drawing the major organic product in the window provided. 
Draw the remaining product of the following reaction.
Predict the carboxylic acid product of the following reaction: Express your answer using the IUPAC name.
Draw the carboxylic acid and amine that form the following amide: