Lab 11 (Aldol Condensation)

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12 Terms

1
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<p>What is the mechanism of the reaction of cyclopentanone with furfural and NaOH?</p>

What is the mechanism of the reaction of cyclopentanone with furfural and NaOH?

  1. First base deprotonates sp3 carbon on cyclopentanone to form enolate

  2. Then carbon attached to pi bond attacks carbonyl on furfural

  3. Once attacked pi electrons shift from carbonyl on furfural

  4. Then water protonates the furfural to make an OH group 

  5. Then an OH deprotonates carbon that attacked furfural

  6. OH group leaves (both leave as H2O) and then C=C bond forms

<ol><li><p><span>First base deprotonates sp<sub>3</sub> carbon on cyclopentanone to form enolate</span></p></li><li><p><span>Then carbon attached to pi bond attacks carbonyl on furfural</span></p></li><li><p><span>Once attacked pi electrons shift from carbonyl on furfural</span></p></li><li><p><span>Then water protonates the furfural to make an OH group&nbsp;</span></p></li><li><p><span>Then an OH deprotonates carbon that attacked furfural</span></p></li><li><p><span>OH group leaves (both leave as H<sub>2</sub>O) and then C=C bond forms</span></p></li></ol><p></p>
2
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<p>Which of the following carbonyl compounds are enolizable (can undergo aldol reaction)?</p>

Which of the following carbonyl compounds are enolizable (can undergo aldol reaction)?

  1. Only carbons with an sp3 carbon with an alpha proton are able to form enolates

    1. Only A, and C ketones can be enolized

      1. D can’t be enolized because there is no proton

3
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<p>What are the structures of the possible products of self condensation of cyclopentanone?</p>

What are the structures of the possible products of self condensation of cyclopentanone?

Basically replace C=O bond with a C=C bond connected to any sp3 carbon

<p>Basically replace C=O bond with a C=C bond connected to any sp<sub>3</sub> carbon</p>
4
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What is the structure of Aliquat 336 and what is its role in the reaction of this experiment?

It functions as a phase transfer catalyst

<p>It functions as a phase transfer catalyst</p>
5
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What is the role of a phase transfer catalyst in this reaction?

Aliquat will be used as a phase transfer catalyst to bring OH- from the aqueous phase to the organic phase so it can react with the furanol and cyclopentanone for the aldol reaction

<p>Aliquat will be used as a phase transfer catalyst to bring OH- from the aqueous phase to the organic phase so it can react with the furanol and cyclopentanone for the aldol reaction</p>
6
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<p>What is the product of aldol self condensation of acetophenone?</p>

What is the product of aldol self condensation of acetophenone?

<p></p>
7
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<p>What are the possible products of aldol condensation of this ketone with benzaldehyde?</p>

What are the possible products of aldol condensation of this ketone with benzaldehyde?

C=C groups between sp3 carbons and aldehyde carbon on benzaldehyde

<p>C=C groups between sp<sub>3</sub> carbons and aldehyde carbon on benzaldehyde</p>
8
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<p>What are the reactions of this aldol condensation?</p>

What are the reactions of this aldol condensation?

Acetophenone is an enolizable carbon, so it can either self react with acetophenone or react with furfural

<p>Acetophenone is an enolizable carbon, so it can either self react with acetophenone or react with furfural</p>
9
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<p>Which of the following protons is most acidic?</p>

Which of the following protons is most acidic?

A

10
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<p>Which of the following carbonyl compounds are</p>

Which of the following carbonyl compounds are

A,D, and E because only these compounds have a neighboring sp3 proton

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<p>Which compound cannot be a (side)product in aldol condensation of furfural with cyclopentanone?</p>

Which compound cannot be a (side)product in aldol condensation of furfural with cyclopentanone?

2 cannot be made because the aldehydes don’t have a neighboring sp3 proton so they are unable to undergo aldol reaction

12
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<p>What is the exact role of Aliquot 336 in reaction?</p>

What is the exact role of Aliquot 336 in reaction?

It acts as a phase transfer catalyst to bring OH into the organic phase to react with the other organic reactants