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WorksheetsOrganic Carbonyl alpha substitution reactions
Total questions: 10
Worksheet time: 20mins
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
