Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
December 24, 2024, 07:24:40 AM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
does this synthesis work?
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: does this synthesis work? (Read 4832 times)
0 Members and 1 Guest are viewing this topic.
rleung
Full Member
Posts: 186
Mole Snacks: +5/-5
I'm a mole!
does this synthesis work?
«
on:
March 20, 2006, 03:22:13 PM »
Hi,
I am wondering if this synthesis works. Thanks.
Ryan
Logged
Albert
Lonely Wanderer
Retired Staff
Sr. Member
Posts: 1050
Mole Snacks: +112/-22
Gender:
Half Decent Pharmaceutical Chemist
Re:does this synthesis work?
«
Reply #1 on:
March 20, 2006, 03:49:24 PM »
I don't think so.
Mind you, do you need to synthesize the final product you drew from that derivative of cyclohexanone? Can't you start from a different compound?
Logged
rleung
Full Member
Posts: 186
Mole Snacks: +5/-5
I'm a mole!
Re:does this synthesis work?
«
Reply #2 on:
March 20, 2006, 04:08:44 PM »
Hi,
Nope, I have to start from the reagent I used and end up with the product I need. If I convert the acyl chloride into an ester using SOCl2/CH3OH, that would be better, right?
Ryan
Logged
Albert
Lonely Wanderer
Retired Staff
Sr. Member
Posts: 1050
Mole Snacks: +112/-22
Gender:
Half Decent Pharmaceutical Chemist
Re:does this synthesis work?
«
Reply #3 on:
March 20, 2006, 04:16:29 PM »
I sincerely doubt you can use NaOH as a base, because I think it'd react with the-CN group to yield a carboxylic acid.
If I were you, I'd choose NaH.
Logged
movies
Organic Minion
Retired Staff
Sr. Member
Posts: 1973
Mole Snacks: +222/-21
Gender:
Better living through chemistry!
Re:does this synthesis work?
«
Reply #4 on:
March 20, 2006, 04:22:59 PM »
Acid chlorides tend to acylate on the oxygen of an enolate in preference to the carbon atom of an enolate.
Logged
netscape
Guest
Re:does this synthesis work?
«
Reply #5 on:
March 22, 2006, 03:06:53 PM »
I'm afraid this synthesis won't work, even using NaH as base and an ester instead of acyl chloride. I see two potential problems:
1) Regioselective issue: There is really no real preference to which side of the cyclohexanone is going to be deprotonated. They are equally substituted.
2) Use of a base to deprotonate the position you want may also lead to elimination of CN- to give an cyclohexenone.
You may get some product , but the yield will be low and it might be messy.
Logged
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
does this synthesis work?