Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Draw the major organic product resulting from the reaction conditions shown below.

The following compound isolated from a marine sponge has been found to have anti-tubercular activity (Tet. Lett. 2007, 8851). Show how it may be constructed by an aldol reaction by drawing a structure of the starting material.

Provide the structure of the Claisen product in the self condensation of methyl phenylacetate.

Consider the reaction shown below. Use pKa values to determine which way the equilibrium lies.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reactions.

Predict the pK_a unit of the indicated proton within +/- 1 pK_a unit.

An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this?

Show how an enolate can add to a carbonyl.

Which of the following is most acidic?

What alkyl halide would you add to perform the following alkylation reaction?

Provide the structure of the aldol product that results when 5-methylhexanal is treated with hydroxide.

Which of the following will alkylate a lithium enolate most rapidly?

What is the approximate pKa of acetone?

How would you perform the following transformation using a Michael addition?

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.