Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
December 09, 2024, 04:00:26 PM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Wolff Kishner?
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: Wolff Kishner? (Read 949 times)
0 Members and 1 Guest are viewing this topic.
sharbeldam
Full Member
Posts: 344
Mole Snacks: +8/-2
Wolff Kishner?
«
on:
June 18, 2020, 02:53:47 PM »
Can it reduce ketones that have functional groups in their chain? for instance if there is an amine involvled.
let's say 4-amino-2-pentanone.
are there specific rules for this reaction?
Thank you
Logged
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21
rolnor
Chemist
Sr. Member
Posts: 2304
Mole Snacks: +154/-10
Re: Wolff Kishner?
«
Reply #1 on:
June 19, 2020, 06:59:32 AM »
What would you say about amino groups and ketone-carbonyl groups, can they react with each other in some way?
Logged
sharbeldam
Full Member
Posts: 344
Mole Snacks: +8/-2
Re: Wolff Kishner?
«
Reply #2 on:
June 19, 2020, 09:14:53 AM »
Yes to produce amines and enamines, but in general if there was a functional group that doesnt react with the ketone, can we do the wolff kishner or does it have to be alkyl?
Logged
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21
rolnor
Chemist
Sr. Member
Posts: 2304
Mole Snacks: +154/-10
Re: Wolff Kishner?
«
Reply #3 on:
June 20, 2020, 03:27:36 AM »
You use hydrazine fot this, a very strong nucleophile so this will be difficult with electrophilic groups on the molecule.
You can also make a dithioacetal from the ketone/aldehyde and use Raney-Ni to de-sulphurize it, this will give the same result as Wold-Kischner and you avoid strong nucleophile.
https://en.wikipedia.org/wiki/Thioacetal
https://en.wikipedia.org/wiki/Raney_nickel
Logged
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Wolff Kishner?