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Show the aldol addition product that would be formed from each of the following compounds:

a. CH₃CH₂CH₂CH₂CHO

b. CH₃CH₂CHO

c. CH₃CH₂C(CH₃)₂CHO

d. CH₂=CHCHO

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For each of the following compounds, indicate the aldehyde or ketone from which it would be formed by an aldol addition:

a. 2-ethyl-3-hydroxyhexanal

b. 4-hydroxy-4-methyl-2-pentanone

c. 2,4-dicyclohexyl-3-hydroxybutanal

d. 5-ethyl-5-hydroxy-4-methyl-3-heptanone

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An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzed aldol addition of propanal.



Answer :

GinnyAnswer

Final answer:

The detailed answer provides examples of aldol addition product formations, sources of aldehydes/ketones in aldol additions, and an explanation of the acid-catalyzed mechanism.


Explanation:

Aldol Addition Product Formation:

  1. CH3CH2CH2CH2CH2CHOH
  2. CH3CHCH2CH2CHOH
  3. CH3CHCH2CH2CHOH

Aldehyde/Ketone Sources:

  1. 2-ethyl-3-hydroxyhexanal: Formed from propanal and acetone.
  2. 4-hydroxy-4-methyl-2-pentanone: Formed from acetone and isobutyraldehyde.
  3. 2,4-dicyclohexyl-3-hydroxybutanal: Formed from cyclohexanone and cyclohexane carbaldehyde.
  4. 5-ethyl-5-hydroxy-4-methyl-3-heptanone: Formed from cyclohexanone and 3-pentanone.

Acid-catalyzed Mechanism:

Mechanism involves protonation of the carbonyl oxygen, enol formation, and subsequent proton transfer for aldol addition.


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