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Organic Chemistry 328 SI
Direct Enolate Alkylation
Malonic Ester Synthesis
Acetoactic Ester Synthesis
Chapter 24 - Condensation Reactions Between Carbonyl Compounds
Exam 3 Next Tuesday 4/19!
Chapter 21, 22, 23, 24 and part of 25
Would still be a good idea to review old reagents
Next Monday at 6-8pm in Rotunda E
Final is less than 4 weeks away
 NaCN / HCl
What is the product?
 I2 (ex) / -OH
 Acetyl Chloride
 Br2 / Acetic Acid
 Li2CO3 / LiBr / DMF
 Ethylene glycol / TsOH
 H2O / H2SO4
 H2SO4 / Removal of H2O
I and enantiomer
IV and enantiomer
At 25˙ C, which pair would form?
I and III
I and IV
II and III
II and IV
 LDA / THF (-78˙C)
II and Enantiomers
Direct enolate alkylation
Aldehyde, ketone, ester or nitriles
Deprotonation (Thermodynamic or Kinetic?)
LDA / THF at -78˙C
KOC(CH3)3 / HOC(CH3)3 at 25˙C
Enolate attacks alkyl halide
*Note: Hindered alkyl halides and halogens bonded to Sp2 carbons (R3CX, CH2=CH2, or C6H5X will not react with enolates
 NaOCH2CH3 / Et. (25˙C)
Which product forms?
 H3O+ / ∆
Hydrolyzed to form beta diacids
Decarboxylation (lose of CO2)
Break molecule at alpha carbon C-C bonds (excluding the carboxylic acid carbon
Acetoacetic Ester Synthesis
Hydrolysis and Decarboxylation
Find alpha carbon, break bonds, add X to separated R groups and form Beta-Keto Ester with alpha carbon
-OH / H2O
Two ketones or aldehydes
Reagent: -OH, H2O
If we react excess butanal with –OH and H2O, which product forms?
Dehydration of ß-Hydroxy Carbonyl compound with a base follows which mechanism?
Aldol product dehydration
=> Elimination, unimolecular, conjugated base
Reagent: H3O+ or -OH
Anionic enolate intermediate (carbanion)
Forms α,β-unsaturated carbonyl compound
Can’t be reconverted into SM
 –OH , H2O
 –OH , H2O
Have a great night studying chemistry