Exam 10: Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions

Rank the following compounds in order of increasing reactivity with a nucleophile.

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: 2-propylpentanoic acid

What is the order of increasing acidity for the following compounds? (least to most)

Choose the best reagent(s) for carrying out the following conversion. a. 1. CH3MgBr, ether 2. H $_3$ O $^+$ b. CH $_3$ COCl c. CH $_3$ OH, acid, heat d. all of the above work

What is the IUPAC name of the following compound?

Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: phenylacetonitrile or phenylethanenitrile

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry. Provide missing structure(s):

Draw the structure of prop-2-enamide.

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. Give major product(s):

Instructions: Provide the missing structure(s) or reagent(s) for each reaction or sequences of reactions. Show all relevant stereochemistry. Provide missing structure(s):

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. Give the major product(s):

Write the complete stepwise mechanism for the basic hydrolysis of acetamide, shown below. Show all electron flow with arrows and draw all intermediate structures.

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. Give major product(s):

Instructions: Consider the data in the table below to answer the following question(s). Refer to instructions. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

What is the correct structure for phenylbenzoate?

Instructions: Provide IUPAC names for the structures in the following question(s). Name:

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: N,N-dimethylformamide

What is the IUPAC name of the following compound?