Aldol? I Barely Know Her!
Michael Jackson Addition
Oxidation Nation: No Mercy Edition
Enamine?
Swern & Burn
Triple Threat: Alkynes & Chaos
100

This species forms when hydroxide removes an α-hydrogen from butanal.

What is an enolate ion?

100

Michael addition is best described as this type of addition.

What is conjugate (1,4-) addition?

100

This oxidation inserts an oxygen between a carbonyl carbon and an R group.

What is Baeyer–Villiger oxidation?

100

Swern oxidation converts alcohols into these functional groups.

What are aldehydes or ketones?

100

Alkynes have this type of hybridization.

What is sp hybridization? 

200

In aldol addition, this functional group is attacked by the enolate nucleophile.

 What is the carbonyl group?

200

The nucleophile in a typical Michael addition is derived from this species.

What is an enolate (often from a β-dicarbonyl compound)?

200

The reagent used in Baeyer–Villiger oxidation is typically this.

What is a peroxy acid?

200

Enamines are formed from ketones and this class of compounds.

What are secondary amines?

200

This base is commonly used to generate acetylide ions.


What is NaNH₂?

300

The intermediate formed after nucleophilic attack before protonation is this type of ion.

What is an alkoxide ion?

300

The electrophile in Michael addition is this type of compound.

What is an α,β-unsaturated carbonyl?

300

In Baeyer–Villiger oxidation, this group migrates preferentially.

What is the larger (more substituted) R group?

300

This base is added in the final step to drive elimination.

What is triethylamine?

300

Acetylide ions act as this in reactions.

What is a nucleophile?

400

The final product of aldol addition between two butanal molecules contains this functional group combination.

What is a β-hydroxy aldehyde?

400

The nucleophile attacks this carbon in the α,β-unsaturated system.


What is the β-carbon?

400

The product formed from ketones after Baeyer–Villiger oxidation is this functional group.

What is an ester?

400

Why does deprotonation occur at the α-carbon in enamine formation?

What is to form a conjugated C=C–N system (stabilized enamine)?

400

Hydrogenation of alkynes with Lindlar catalyst gives this product.

What is a cis-alkene?

500

Why is the enolate considered unstable in aqueous conditions during aldol reactions?

What is it is rapidly protonated due to water acting as a proton donor?

500

Why are enolates used in Michael additions instead of strong bases?

What is they are weak bases that favor conjugate addition over direct carbonyl attack?

500

Why is Baeyer–Villiger considered regiospecific?

What is oxygen inserts selectively next to the more substituted group due to migration aptitude?

500

What drives the final step of Swern oxidation to form the carbonyl?

What is intramolecular proton abstraction leading to elimination and formation of dimethyl sulfide?

500

Why are terminal alkynes acidic compared to alkanes?
 

What is sp hybridization stabilizes the conjugate base (acetylide ion)?