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Organic Chemistry II Carbonyl Chemistry. Chemistry of enols and enolates

Semester 1, 2022-2023
Class: Major: Chemistry
Student: Date - Month - Year: Grade:

Topics:
1) acid- and base-catalyzed enolization. The formation of carbon-alpha nucleophiles
2) acid- and base-catalyzed aldol (self-, crossed, cyclization)
3) directed aldol: control selectivity of crossed aldol through the formation of kinetic or thermodynamic
enolates and silyl enol ethers
4) alkylation of enolates or enamines
5) halogenation (Cl2, Br2, I2). haloform reactions of methyl ketones
6) 1,2- and 1,4-addition
7) Michael and Robinson (MAD) annulation
8) retrosynthesis of C-C bond formation: 1,3- and 1,5-models

Question 1: Enolization. Identify the most acidic alpha hydrogen in the following molecules? Write the
corresponding enols and enolate ions?

Question 2: Enolization. How to stabilize the following base by resonance?

Question 3: Aldol reactions. Provide the products of the following reactions?

Question 4: Concept maps. Provide the products (for each step) of the following reactions of phenyl methyl
ketone?
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Question 5: Alkylation and Halogenation. How to complete the following reactions?

Question 6: 1,2- and 1,4-Addition. How to complete the following reactions?

Question 7: Mechanism. Adehydes that have no alpha hydrogen undergo an intermolecular oxidation-
reduction when they are treated with concentrated base. Provide mechanism of the reaction?

Question 8: Retrosynthesis and Synthesis. How to synthesize the compounds I–VI using the indicated
reactions?

Question 9: Retrosynthesis: 1,3- and 1,5-models. How to synthesize the following compounds from the
starting materials obtained from 1,3- or 1,5-retrosynthetic models?