Organic Carbonyl alpha substitution reactions

Which of the following is not correct?

• Tautomers are constitutional isomers.

• Tautomers rapidly interconvert.

• The enol form is generally more stable.

• Tautomerization is catalyzed by both acids and bases.

• All of the answers are correct with respect to tautomers

Examine the following generalized structure. It represents

• the acid catalyzed intermediate between an keto and enol tautomer.

• the base catalyzed intermediate between an keto and enol tautomer.

• one of the resonance forms of the acid catalyzed intermediate between an keto and enol tautomer.

• one of the resonance forms of the base catalyzed intermediate between an keto and enol tautomer.

Consider the following molecular model. Atoms other than carbon and hydrogen are labeled. Bromination of the substance represented would be dependent on the concentration of:

• ketone

• acid

• halogen

• ketone and acid

• ketone and halogen

The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is:

• 1-bromooctane

• 1-bromohexane

• 1-bromopentane

• 1-bromodecane

• 1-bromoundecane

Using the acetoacetic ester synthesis, to produce 5-methyl-2-heptanone, the alkyl halide that should be used is:

• 1-bromo-2-methylpentane

• 1-bromo-2-methylnonane

• 1-bromo-2-methylbutane

• 1-bromo-2-methyldecane

• 1-bromo-5-methylheptane

The following substance is produced using acetoacetic ester synthesis. Atoms other than carbon and hydrogen are labeled. Which of the following regions of an IR spectrum could be used to monitor the progress of the reaction?

• 2850 - 29060 cm^–1

• 2500 - 3100 cm^–1

• 1670 - 1780 cm^–1

• 500 - 600 cm^–1

• Either 1670 - 1780 cm^–1 or 500 - 600 cm^–1

Which of the hydrogen atoms indicated by a number is the most acidic in the structure below? Atoms other than carbon and hydrogen are labeled.

• 1

• 2

• 3

• 4

The starting material A in this reaction sequence is called _____.

• a β-keto ester

• an α-carboethoxy ketone

• a malonic ester

• an acetoacetic ester

Conversion of A into B is a type of reaction termed _____.

• an acylation

• an enolation

• an alkylation

• a phenylation

Compound X, diethyl propanedioate, is more commonly known as _____.

• ethyl acetoacetate

• acetoacetic ester

• oxalic ester

• malonic ester