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Offline maverick1996

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Organic Synthesis question
« on: March 29, 2016, 11:07:56 AM »
I'm a first year undergrad - just doing some practice with organic chem and came across this question
Didn't know how to go about doing it, can somebody help??

the question says that other readily available organic starting materials are available

Thanks in advance
« Last Edit: March 29, 2016, 12:56:06 PM by maverick1996 »

Offline Borek

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Re: Organic Synthesis *delete me*
« Reply #1 on: March 29, 2016, 12:31:17 PM »
You have to show your efforts at solving the problem to receive help, this is a forum policy.
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Offline maverick1996

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Re: Organic Synthesis *delete me*
« Reply #2 on: March 29, 2016, 12:51:01 PM »
You have to show your efforts at solving the problem to receive help, this is a forum policy.

thank you for telling me this :)

I tried using ozone with a Zn cat. to cleave the double bond
The i though of making an oxime and reducing that with LiAlH4 to make an amine
and then react this amine with an aldehyde to make an Imine
Reducing this imine with NaBH4 maybe??

But the thing that was really confusing me is the alcohol group

I don't really know - I have never really seen a question like this

Thank you

Offline discodermolide

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Re: Organic Synthesis question
« Reply #3 on: March 29, 2016, 01:10:06 PM »
Reduction will give the amine.
How do amines react with epoxides?
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Offline Alwin Kristen

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Re: Organic Synthesis question
« Reply #4 on: March 29, 2016, 02:39:57 PM »
sounds like a plan  :) From what would you do an oxime?
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Offline maverick1996

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Re: Organic Synthesis question
« Reply #5 on: March 29, 2016, 03:53:20 PM »
sounds like a plan  :) From what would you do an oxime?

I honestly don't know - this has been bugging me for a while

Offline maverick1996

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Re: Organic Synthesis question
« Reply #6 on: March 29, 2016, 04:04:33 PM »
Reduction will give the amine.
How do amines react with epoxides?

Uhm I'm not quite sure, haven't come across an amine reacting with an epoxide so far in my undergrad - but I'm guessing it's going to be a standard SN2 reaction??

I'm probably wrong though

Offline AWK

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Re: Organic Synthesis question
« Reply #7 on: March 29, 2016, 04:27:09 PM »
AWK

Offline maverick1996

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Offline Alwin Kristen

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Re: Organic Synthesis question
« Reply #9 on: March 30, 2016, 02:58:27 AM »
I wonder if it is even necessary to make oxime from anything. Can you react primary amine with pivaladehyde which you get from cleaving doublebond with ozone? Is there commercially available primary amine you could use?
Let us learn to dream, we then might find the truth. - F. A. Kekulé

Offline maverick1996

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Re: Organic Synthesis question
« Reply #10 on: March 30, 2016, 05:24:14 AM »
Thanks for all your help

What do you think of this?

Offline AWK

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Re: Organic Synthesis question
« Reply #11 on: March 30, 2016, 05:33:01 AM »
Instead HOCH2COCl(easy cyclization of 2 molecules) use ClCH2CH2OH(epichlorohydrine) or oxirane. A few steps less.
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Offline kriggy

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Re: Organic Synthesis question
« Reply #12 on: March 31, 2016, 09:10:33 AM »
You could also get aldehyde from the ozonolysis and then do reductive amination that will save you some steps

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