Can Synthesis of http://harishkukreja.neargeek.net/Synthesis.jpg be Achieved?

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Discussion Overview

The discussion revolves around the feasibility of a specific chemical synthesis as illustrated in a provided image. Participants explore various synthetic routes, reactions, and methodologies relevant to organic chemistry, particularly focusing on the challenges and steps involved in achieving the synthesis.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Mathematical reasoning

Main Points Raised

  • One participant expresses difficulty in achieving the synthesis and lists allowed reactions, indicating a need for assistance.
  • Another participant suggests cleaving the double bond through oxidation to create carbonyl sites, proposing an intramolecular condensation reaction to form the desired ring structure.
  • A subsequent reply clarifies the use of KMnO4 oxidative conditions and claisen condensation as part of the proposed synthesis route.
  • One participant claims to have figured out the synthesis, stating it involves 12 steps and invites others to share their methods.
  • Another participant expresses interest in comparing their steps with the original poster's synthesis.
  • A participant points out a potential violation of Bredt's rule in the proposed synthesis, suggesting that dehydration may not work as intended.
  • A participant acknowledges their lack of exposure to Bredt's rule and seeks advice on how to address the issue.
  • Another participant mentions having a different synthesis route that takes 7 steps but expresses uncertainty about some steps.
  • Discussion includes a light-hearted remark about the teaching of organic chemistry at the high school level.
  • One participant requests to see the 7-step synthesis, indicating a desire to learn from different approaches.
  • A later reply critiques potential issues with isomers in a specific oxidation reaction and the challenge of saponifying a lactone without affecting a methyl ester.

Areas of Agreement / Disagreement

Participants present multiple competing views on the synthesis routes and express uncertainty about specific steps. There is no consensus on the best approach or resolution of the challenges raised.

Contextual Notes

Participants reference specific organic chemistry concepts and reactions, indicating a reliance on their understanding of these topics. The discussion highlights varying levels of knowledge and exposure to organic chemistry principles among participants.

Who May Find This Useful

This discussion may be of interest to students and enthusiasts of organic chemistry, particularly those exploring synthesis techniques and problem-solving in chemical reactions.

SplinterIon
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Hey y'all

I'm wondering whether it's possible for the following synthesis to occur and how?:

http://harishkukreja.neargeek.net/Synthesis.jpg

The thing is, after bashing my head against it for about 2 hrs - I've really gotten nowhere :cry: . A few of the rxn's we're allowed to use are:

Hydrogenation (except you can't undo it )
Halogenation + De
Hydrohalogenation + De
Oxidation (KMnO4)
Ozonation (O3)
Esterification
Amide formation
Reduction (LiAlH4 and/or NaBH4).
Hydration + De (H2SO4 conc/dilu.)

Using dehydration + 2*oxidation + esterification I can change the double bond to the bottom chain. using a similar process also yields the top (though in an isomer form). I'm however badly stuck when dealing with the middle section - further the double reactive sites are also bugging me - and blocking isn't really helping me.

Any help would be appreciated and I will worship you forever o:)
 
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How about cleaving the double bond first, through oxidation. You'll have two carbonyl sites. Note that the left carbonyl created from this is part of an enolate derivative. Using a suitable base, perform the intramolecular condensation reaction, the alpha carbon will react with ring carbon #3 (the other newly formed carbonyl group). This will give you the exact ring structure you need. We'll go on from here.
 
I'm just going to clarify a bit more...KMn04 oxidative conditions, claisen condensation, and we can go on from there...if you're still around
 
I'm sorry for the delay - forgot I posted the question on the site :rolleyes:

I figured it out (double checked with an independent source) - and I'll post it as soon I have access to my scanner (~Monday). Turned out to be relatively easy after the 2 tricky initial steps. In total there are 12 steps to the synthesis. I was told there were would be about 10-15 depending on the way one would go about it - so I'm happy with the result. If you can do it in less than 10 I'm interested :cool:

Thanks for your help though.
 
yeah, be sure to post the results, as I'm sure that many here are interested, I want to see if you're first two steps corresponds with mine.
 
Here it is - just in skeletal format after dashing it off in a few minutes. If you spot any error, chalk it down to being in a rush - unless of course it's a major error, then please do tell. Ignore the term "possibility" - the synthesis continues from the last diagram to "#1" onwards (I just got lazy to draw the rings for each). See the first message for the inital and final diagrams.
 

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You've got a Bredt's rule violation in there. The dehydration won't work.

http://www.iupac.org/goldbook/B00732.pdf
 
We were never taught or exposed to Bredt's rule in class (lowly high school kid) - so thank you for pointing that out. What would you suggest I do to rectify the situation?
 
I dunno. It's a tough question. I came up with an very different route from yours which takes 7 steps, but there are one or two steps that I don't really like myself.

I can't think of an easy solution to your dehydration problem though. Sorry.
 
  • #10
since when did they start teaching organic chemistry in high school? I'll try taking a stab at this problem when I have the time.
 
  • #11
@ movies: could you please post your 7 step one - would like to see it (don't personally care if it works or not - just would like to learn something from it). Furthermore, just talked to my teacher, apparently he doesn't care about the violation - didn't even expect anyone to find out that problem.

GCT said:
since when did they start teaching organic chemistry in high school?

AP chemistry class - and the teacher is a bit of organic junkie - apparently it was what he did for his masters.
 
  • #12
Alright, just don't go trying to pass it off as your own work. ;D

I'd bet you've never even seen 4 of these 7 reactions before.

The problems I see are with the isomers in the Baeyer-Villiger oxidation (it'd probably favor the undesired product) and with saponifying the lactone without saponifying the methyl ester. It might work though...

I hope it's helpful to you.
 

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