November 24, 2024, 03:43:07 PM
Forum Rules: Read This Before Posting


Topic: Is this synthesis feasible?  (Read 2223 times)

0 Members and 2 Guests are viewing this topic.

Offline Norepi

  • Very New Member
  • *
  • Posts: 1
  • Mole Snacks: +0/-1
  • Gender: Male
Is this synthesis feasible?
« on: September 16, 2016, 06:56:50 AM »
Hey I'm new to this forum. I'm very arrogant about my OChem knowledge, but alas I need help.

Reaction: 4'-fluorobenzalhyde refluxed for 6hrs with 10 mol% eq. of ammonium acetate, 1.2 eq. of nitroethane and 20 wt. % of IPA, (IPA is the solvent) yielding around 85%
4-(fluorophenyl)-2-nitropropene.

I did a retrosynthetic analysis of this reaction, and it is very perplexing to say the least. The reaction involves several "denotions" of electrons. Is this synthesis even feasible? I found it online somewhere, but I can't recall where. I'm baffled about a methyl group and what happens to the β-ketone.

Any help is MUCH obliged!  :)

Offline TheUnassuming

  • Chemist
  • Full Member
  • *
  • Posts: 461
  • Mole Snacks: +48/-1
Re: Is this synthesis feasible?
« Reply #1 on: September 16, 2016, 07:38:22 AM »
Might want to read the forum rules on controlled substances.
When in doubt, avoid the Stille coupling.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Is this synthesis feasible?
« Reply #2 on: September 16, 2016, 10:23:25 AM »
Hey I'm new to this forum. I'm very arrogant about my OChem knowledge, but alas I need help.

Reaction: 4'-fluorobenzalhyde refluxed for 6hrs with 10 mol% eq. of ammonium acetate, 1.2 eq. of nitroethane and 20 wt. % of IPA, (IPA is the solvent) yielding around 85%
4-(fluorophenyl)-2-nitropropene.

I did a retrosynthetic analysis of this reaction, and it is very perplexing to say the least. The reaction involves several "denotions" of electrons. Is this synthesis even feasible? I found it online somewhere, but I can't recall where. I'm baffled about a methyl group and what happens to the β-ketone.


Ah, we feel your arrogance! Who else would think of doing a "retrosynthetic analysis" if the reactants and even the product was given? Plus, "the reaction involves several "denotions" of electrons."? This reaction seems straight forward, so I am baffled by anyone's being baffled. I'm further baffled by a question about "a methyl group" and "the β-ketone" in a reaction either not involving a methyl group or even having a β-ketone.

My experience is that a lot of the posters are really pretty smart, however, they are not good mind readers. Perhaps you could ask someone to find you a ladder so you do not become injured in dismounting. What is baffling?
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links