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Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

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Question 1

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Which of the following compounds will not undergo reaction with an enolate?

A) 1-pentene
B) bromine
C) propanal
D) 1-bromobutane
E) benzoyl chloride

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Question 2

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Draw a mechanism and provide the structure of the aldol product that results when 4-methylpentanal is heated with sodium hydroxide.

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Question 3

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In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a ________.

Provide the structure of the major organic product which results when PhCO₂CH₂CH₃ and CH₃CH₂CO₂CH₂CH₃ are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, heat.

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, heat.

Disregarding stereoisomers, how many different enols can the β-diketone CH₃COCH₂COCH₂CH₃ form?

What product results when pentanal is heated with sodium hydroxide?

Arrange the following compounds in order of increasing acidity: acetone, ethyl acetoacetate, ethyl acetate, and ethanol.

When 2-methylcyclohexanone is treated with catalytic base in excess D₂O, how many deuterium atoms become incorporated in the organic compound?

What type of reaction is shown below?

What crossed-aldol product results when butanal is heated in the presence of excess benzaldehyde and sodium hydroxide?

Provide the structure of the major organic product which results when PhCH₂CHO is treated with NaOH.

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

Provide a synthesis of the compound shown below from cyclopent-2-en-1-one and acetoacetic ester.

Which of the following is another name for the product of an aldol condensation?

Which of the following is the best Michael acceptor?

When compound X is heated, PhCOCH(CH₃)₂ and CO₂ are produced. Offer a structure for compound X.

Provide the major organic product of the reaction shown below.

Complete the following synthesis by filling in the missing reagents.