Ch1b2010_week8_b

Ch1b2010_week8_b - addition of organometallic reagents to...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Organometallic Reagents: Carbon Nucleophiles organometallic reagents : a carbon is bound to a more electropositive metal, resulting in a polar covalent bond with substantial negative charge on carbon MO considerations:
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
How to Make Organometallic Reagents Grignard reagents: Organolithiums:
Background image of page 2
Organometallic Reagents are Strong Bases organometallic reagents will react with H 2 O and other acidic protons remember: a base can deprotonate acids with pK a values that are lower than it’s conjugate acid.
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Organometallic Reagents Add to Carbonyls remember, carbonyls are electrophilic on carbon: a general mechanism for organometallic addition to carbonyl:
Background image of page 4
Organometallic Reagents Add to Carbonyls
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: addition of organometallic reagents to carbonyls form CC bonds aldehyde + organometallic 2 alcohol 3 alcohol ketone + organometallic generally speaking: Divergent Reactivity in Carbonyl Addition Reactions all carbonyl addition reactions can roughly be divided into two categories: the fate of carbonyl additions depends on both : the nature of the carbonyl electrophile the nature of the nucleophile Addition of Organometallics to Esters esters undergo double-addition of organometallic reagents Why Are Ketones More Electrophilic than Esters? can use resonance structures to rationalize reactivity trend: trend in carbonyl electrophilicity:...
View Full Document

Page1 / 8

Ch1b2010_week8_b - addition of organometallic reagents to...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online