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Read Experiment 10 - Aldol Pre-lab 10 Notebook Items Complete online Pre-lab 10 Experiment 8 & 9 Post-labs due next week You will check-out of lab next week after completing the Aldol lab See page 131 in the lab manual for details Final Exam scheduled for Monday, Nov. 30 from 7 to 9p Email me ASAP if this time is a conflict for you! (if you havent already)
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enol
OH R(H) + H
The interconversion of two isomers via a proton and double bond shift is called tautomerization.
nucleophilic here
The !-proton of the carbonyl is somewhat acidic because its conjugate base is resonance stabilized.
!-hydroxyaldehyde
self-aldol In a ___________ condensation, two molecules of the same aldehyde or ketone react to form the product, like that shown above. crossed-aldol In a ______________ condensation, one molecule of an aldehyde or ketone reacts with a different aldehyde or ketone to form the product.
O O H OH
enolate formation
O O H
addition
H O O
OH OH O + OH
proton transfer
Synthesis of trans-p-Anisalacetophenone
new carbon-carbon bond
O + H O O O O NaOH + H2O
acetophenone
p-anisaldehyde
trans-p-anisalacetophenone
Formation of !-hydroxyketone:
OH
1st Step
O
OH
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A Redox Reaction
aldehyde
carboxylic acid
alcohol
The Mechanism:
O R H OH HO R O H
addition
HO R
O H R
O H R
O OH
hydride transfer
O R OH
~H+ + R O R
O O
OH
proton transfer
1H
NMR of trans-p-Anisalacetophenone
O H
integration
H O
Remember, when assigning peaks in the NMR spectrum, start with the easiest assignments first.
Representative J-Values
O H
O
H H
H Ho
Hm
Hp
J = 6.5 - 8.5 Hz
J = 1.0 - 3.0 Hz
Ha Hb Ha
Hb
Ha
Hb
0 - 3 Hz
11 - 19 Hz
6 - 11 Hz
J = 15.6 Hz
J = 15.6 Hz
less shielded
more shielded
H beta to carbonyl
H alpha to carbonyl
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H" H!
H" H!
H" H!
H" H!
!+ !+
!+ !+
O
!+
The partially positive positions on both rings are less shielded than the other positions.
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!" !"
O
!+ !+ !"
!"
O
!+
Use the above resonance arguments and electronegativity arguments to finish up the assignments.
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!+ !+ !"
!"
O
!+
H!
Hpara
H"
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For Next Week#s Lecture... Next weeks lecture will be a review session in preparation for the Final Exam.
Focus on Spectroscopy Come prepared with questions about any portion of the course Final Exam locations TBA next week A note on possible TA strike
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