January 15, 2025, 10:44:05 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1] 2   Go Down

Topic: Organic synthesis  (Read 10426 times)

0 Members and 2 Guests are viewing this topic.

Offline zacher

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Organic synthesis
« on: July 12, 2013, 07:03:43 PM »
Hello guys, do you have some idea how can I make this synthesis ? Thank you for answers
Logged

Offline Borek

  • Mr. pH
  • Administrator
  • Deity Member
  • *
  • Posts: 27897
  • Mole Snacks: +1816/-412
  • Gender: Male
  • I am known to be occasionally wrong.
    • Chembuddy
Re: Organic synthesis
« Reply #1 on: July 13, 2013, 03:23:38 AM »
You have to show your attempts at solving the question to receive help. This is a forum policy. You will not get any help before you will post your own suggestions as to how synthesize the final product, or at least some possible steps leading in the right direction.

This is not a chemical engineering problem, but an organic chemistry problem, please post your questions in appropriate forums.
Logged
ChemBuddy chemical calculators - stoichiometry, pH, concentration, buffer preparation, titrations.info

Offline zacher

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: Organic synthesis
« Reply #2 on: July 13, 2013, 07:29:57 AM »
I made  a lot of synthesis but this one is really hard. So I dont have even idea how to start.. Maybe by some oxidation because I have to open this system of two cyklohexanes. I have to make it somehow because one girl from my high school will not be possible to study next year. I know that this is not right phorum for it but I just asked cause I'm totally lost :/
Logged

Offline camptzak

  • Full Member
  • ****
  • Posts: 159
  • Mole Snacks: +12/-11
Re: Organic synthesis
« Reply #3 on: July 13, 2013, 02:52:04 PM »
start from the target molecule, and work backwards towards your stating material.
Logged
"Chance favors the prepared mind"
-Louis Pasteur

Offline curiouscat

  • Chemist
  • Sr. Member
  • *
  • Posts: 3006
  • Mole Snacks: +121/-35
Re: Organic synthesis
« Reply #4 on: July 13, 2013, 11:02:55 PM »
Quote from: zacher on July 13, 2013, 07:29:57 AM
I made  a lot of synthesis but this one is really hard. So I dont have even idea how to start.. Maybe by some oxidation because I have to open this system of two cyklohexanes. I have to make it somehow because one girl from my high school will not be possible to study next year. I know that this is not right phorum for it but I just asked cause I'm totally lost :/

At least take some effort in drawing your problem  a bit properly and neatly!

C1CCCC2=C1CCCC2  :rarrow: 1  :rarrow: 2  :rarrow: 3  :rarrow: 4  :rarrow: 5 :rarrow: 6  :rarrow:C1CCC(CCCCCO)(C)C1N
« Last Edit: July 13, 2013, 11:24:58 PM by curiouscat »
Logged

Offline zacher

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: Organic synthesis
« Reply #5 on: July 14, 2013, 08:44:14 AM »
I always start from backwards, there is no another way for this synthesis.. But I can't make it anyway...
Logged

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Organic synthesis
« Reply #6 on: July 14, 2013, 09:22:50 AM »
Please show what you have done so far - it's a forum rule. How could that starting alkene be fuctionalised? How do you propose to form the 5-membered ring?

I think I have a reasonable solution, but let's see what you have so far.
Logged
My research: Google Scholar and Researchgate

Offline zacher

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: Organic synthesis
« Reply #7 on: July 14, 2013, 04:00:52 PM »
I would make oxidation, then I will have 2 ketone groups... then I could make reduction by NaBH3CN + NH3.. then I will have instead of ketone groups amino groups what is needed... but I'm not sure if it is good idea
Logged

Offline zacher

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: Organic synthesis
« Reply #8 on: July 17, 2013, 07:31:07 PM »
this is not so bad, what do you think guys ?
Logged

Offline magician4

  • Chemist
  • Full Member
  • *
  • Posts: 567
  • Mole Snacks: +70/-11
Re: Organic synthesis
« Reply #9 on: July 17, 2013, 10:33:02 PM »
step two denotes the conditions for aldol reaction, right?

... and I would disagree with the reaction product you've shown resulting thereof

in my opinion, you'll end up with something like this instead:

O=C1CCCCC2(O)CCCC12


regards

Ingo
Logged
There is a theory which states that if ever anybody discovers exactly what the Universe is for and why it is here, it will instantly disappear and be replaced by something even more bizarre and inexplicable. There is another theory which states that this has already happened.
(Douglas Adams)

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Organic synthesis
« Reply #10 on: July 18, 2013, 02:08:13 AM »
I think the aldol product will dehydrate also. Since this is a more advanced problem I don't want to give too much away, but I can suggest Beckmann rearrangement as a one reaction.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline magician4

  • Chemist
  • Full Member
  • *
  • Posts: 567
  • Mole Snacks: +70/-11
Re: Organic synthesis
« Reply #11 on: July 18, 2013, 02:45:58 AM »
Quote
I think the aldol product will dehydrate also.
I was unsure about that bit: (i)we would build a Bredt-olefine, (ii) aldol condensation is, if memory serves, supported by some type of coplanar arrangement of the Pi-electrones of the C=O group and those of the C=C bond to be, which should be somewhat hindered due to the interconnected ring systems.

furthermore, the question about which ring the doublebond would show up in was a bit unclear to me

Quote
...but I can suggest Beckmann rearrangement as a one reaction.
I would second that


regards

Ingo
Logged
There is a theory which states that if ever anybody discovers exactly what the Universe is for and why it is here, it will instantly disappear and be replaced by something even more bizarre and inexplicable. There is another theory which states that this has already happened.
(Douglas Adams)

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Organic synthesis
« Reply #12 on: July 18, 2013, 03:01:56 AM »
Quote from: magician4 on July 18, 2013, 02:45:58 AM
Quote from: Orgopete
...but I can suggest Beckmann rearrangement as a one reaction.
I would second that

We are all on the same page!
Logged
My research: Google Scholar and Researchgate

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Organic synthesis
« Reply #13 on: July 18, 2013, 07:59:37 PM »
Quote from: magician4 on July 18, 2013, 02:45:58 AM
Quote
I think the aldol product will dehydrate also.
I was unsure about that bit: (i)we would build a Bredt-olefine, (ii) aldol condensation is, if memory serves, supported by some type of coplanar arrangement of the Pi-electrones of the C=O group and those of the C=C bond to be, which should be somewhat hindered due to the interconnected ring systems.

furthermore, the question about which ring the doublebond would show up in was a bit unclear to me

Bredt's rule is about the smallest ring with a trans double bond. It was 10 in the starting material and 10 in the aldol product. Besides, I need that double bond for the next reaction.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline magician4

  • Chemist
  • Full Member
  • *
  • Posts: 567
  • Mole Snacks: +70/-11
Re: Organic synthesis
« Reply #14 on: July 19, 2013, 12:21:02 AM »
Quote
Besides, I need that double bond for the next reaction.

I didn't doubt that for even a second....

but then: any idea how to ensure that it'll lead to the "right" side?
as I said, that bit gave me a headache...


regards

Ingo
Logged
There is a theory which states that if ever anybody discovers exactly what the Universe is for and why it is here, it will instantly disappear and be replaced by something even more bizarre and inexplicable. There is another theory which states that this has already happened.
(Douglas Adams)
Pages: [1] 2   Go Up
« previous next »
Sponsored Links