Exam 21: Carboxylic Acid Derivatives

Provide the major organic product of the following reaction.

What are the products from the reaction of excess methyl magnesium bromide with ethyl acetate followed by H₃O⁺?

Shown below is the structure of Lactimidomycin, a potent inhibitor of cell migration, proliferation and protein synthesis. Identify the carboxylic acid derivative/s in the structure of Lactimidomycin.

Distamycin and derivatives have exhibited antiviral, antibiotic, and antitumor activity by binding to the minor groove of DNA (J. Med. Chem. 2004, 2133). Place a line through each bond of distamycin that would be cleaved by acid hydrolysis.

A nitrile can be made by dehydrating an amide. However, for this reaction to occur, the amide must be ________.

Provide the IUPAC name for HCONHCH₂CH₂CH₃.

Predict the major product of the following reaction.

Predict the major organic product from the following reaction.

Cyclic amides are called ________.

Which of the following are intermediates in the acid hydrolysis of an amide?

Provide a detailed, stepwise mechanism for the reaction of propanoic anhydride with phenol.

Draw the product resulting from the following reaction. Indicate any relevant stereochemistry.

Predict the major product of the following reaction.

Starting from methylpropane, how could you make methyl isobutyrate?

What is the common name for the following carboxylic acid derivative?

Predict the major organic product of the following reaction:

Using ¹H NMR, how would you tell the two esters apart?

List the following five compounds, ethanamide, 1-propanol, methyl formate, acetic acid, and propanenitrile, in order of increasing boiling point. Start with the lowest boiling compound.

Arrange the carboxylic acid derivatives below in order of increasing reactivity towards nucleophilic acyl substitution.

Predict the major product of the following reaction.