Reagents in Nucleophile Addition

In this reaction, an enolate reacts with another carbonyl

In Aldol reactions, an enolate reacts with another carbonyl

Nucleophilic Addition

What is this type of reaction?

This reagent will convert a ketone to an tertiary alcohol

Grignards (RMgBr) add an alkyl group to a ketone

This reagent will convert a ketone to an secondary alcohol

NaBH4 (or other hydrides) will add a hydride to a ketone

This reagent will convert a ketone to an alkene

Ph3P=CH2 will react with ketones to form alkenes

In this reaction, a _______ reacts with an aldehyde to form a beta-hydroxyketone

In aldol reactions, the enolate ion reacts with a carbonyl

In this reaction, a _______ reacts with an aldehyde to form an enone

When an aldol reaction is heated, the enone is formed

This reagent will add a cyano group to a ketone.

NaCN

This reagent adds a RCC (alkynyl group) to a ketone.

NaCCR (triple bond)

This reagent can add a vinyl group (RCH=CH) to a ketone.

RCH=CHLi or RCH=CHMgBr

This reagent will convert a ketone into an enolate nucleophile

Base (OH-, LDA, etc)

This reagent will convert an alkyne into an acetylide nucleophile

Strong Base (NaH, NaNH2, LDA, BuLi)