Carbonyls
An equilibrium to make sure to look out for
What is keto-enol tautomerism?
Cannot be used with any acidic functional groups
What is the Grignard reagent?
Describe 1st step of imine formation.
Addition to carbonyl then proton transfer.
2 reagents commonly used to reduce aldehydes/ketones to alcohols
What are NaBH4 and LiAlH4?
This can lead to the haloform reaction.
What is base promoted alpha halogenation?
This rxn makes alkenes out of aldehydes and ketones.
What is the Wittig Reaction?
Is the less reactive organometallic reagent.
What is the Gilman reagent?
Describe 2nd step of imine formation.
Loss of H2O and proton transfer to solvent.
Why are those 2 reagents commonly used?
A source of H:- (powerful nucleophile).
The name for the Wittig zwitterion.
What is an ylide?
This reaction can be used to make tertiary alcohols from ketones (given acidic workup is the second step)
What is the Grignard reaction?
What is the structure of the Gilman reagent?
[R-Cu-R]-[Li]+
Describe hemiacetal formation steps in your own words.
...
Chromates can oxidize this carbonyl functional group.
What is an aldehyde?
The structure for the ylide is?
Ph3P=CHR
Why is the carbonyl usually the "electron sink"?
Inductive & resonance effects
This works well for Sn2 type reactions
What is Gilman reagent?
Describe Wittig reaction in ur own words.
Ylide attacks at carbonyl C and then that O attacks the P and forms the oxaphosphatine intermediate which then forms the alkene.
Aldehydes are reduced to what alcohol?
Primary.
This can be used as a protecting group.
What is an acetal?
Explain in ur own words what those effects are?
...
Compare and contrast how charges are distributed on the Gilman and Grignard reagents.
Gilman: (-) on Cu and (+) on Li
Grignard: (-) on R and X, and (+) on Mg
Name a reaction where the carbonyl isn't the electrophile.
Alpha halogenation (or any other reaction where you pull off alpha hydrogen)
Ketones are reduced to what alcohol?
Secondary
Give a situation when you can stop at the hemiacetal
The hemiacetal is cyclic.