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Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

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Question 1

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What crossed-aldol product results when propanal is heated in the presence of excess 2,2-dimethylpropanal and sodium hydroxide?

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Question 2

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What two molecules were condensed in an aldol reaction to produce (CH₃)₃CCH=CHCOCH₃?

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What type of product results when 3-pentanone is treated with LDA (lithium diisopropylamide) at low temperature?

Provide a detailed, stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone, hydroxide and iodine.

Provide the sequence of synthetic steps required to produce N-cyclohexyl-2-bromopropanamide from propanoic acid.

What iminium salt is produced in the reaction shown below?

Provide the major organic product of the following reaction.

The structure below is in equilibrium with what tautomer? Draw the structure of the tautomer.

What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed α-bromination of a ketone?

For the equilibrium shown below, is the K_eq greater or less than 1?

Complete the following reaction by filling in the necessary reagents.

Provide the sequence of reagents needed to convert (CH₃CH₂O₂C)₂CH₂ to 2,5-dimethylhexanoic acid.

Which of the following ketones will give a positive iodoform test?

Which of the following structures could be constructed by way of a malonate ester alkylation?

Provide the structure of the ester that would undergo self-condensation to yield the β-ketoester shown below.

Provide the major organic product of the following reactions.

What is the approximate pKa of acetone?

Show how the following compound can be synthesized using an Aldol Condensation reaction.

The following structure was used in the synthesis of a complex natural product shown to have cytotoxic activity (Org. Lett. 2006, 5585). Show how this structure may be constructed by a Robinson annulation by indicating the necessary starting materials.

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