Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Provide a detailed, stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.

Provide the sequence of reagents needed to convert (CH₃CH₂O₂C)₂CH₂ to cyclopentanecarboxylic acid.

Why is the acid-catalyzed halogenation of ketones generally preferred over the base-promoted halogenation?

Draw a correct structure of the expected product for the following reaction.

Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

Complete the following reaction by filling in the necessary reagents.

In the iodoform reaction, a methyl ketone is converted to the ________ upon treatment with excess iodine and hydroxide.

What organic compounds are produced when 2-pentanone undergoes the haloform reaction upon treatment with HO^- and excess Br₂?

Provide the major organic product of the reaction shown below.

Provide the structure of the enol of 2,2,4-trimethyl-3-pentanone.

Provide the sequence of reagents needed to convert CH₃CH₂O₂CCH₂COCH₃ to 7-methyl-2-octanone.

A Claisen condensation results in a β-ketoester. Explain why a second ester enolate does not add to this

What two molecules were condensed in an aldol reaction to produce

What iminium salt is produced in the reaction shown below?

What two molecules were condensed in an aldol reaction to produce

What two organic starting materials are required to produce cinnamaldehyde via a crossed aldol condensation followed by dehydration?

What is the approximate pKa of diethyl malonate?

Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?

Predict the major organic product of the following reaction:

What additional starting material is needed to complete the following transformation?