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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: smdelgado on January 09, 2020, 01:49:38 AM

Title: Reaction conditions
Post by: smdelgado on January 09, 2020, 01:49:38 AM
Hi all!
Can someone help me identify reaction conditions (reagents and conditions) from A:
C=CCC(O)CC=C

to B:
OCCC(O)CCO

Thanks in advance!
Title: Re: Reaction conditions
Post by: sharbeldam on January 09, 2020, 02:50:43 AM
You need to show your try, are you in college? have you learned alkene reactions? markovnikov's rule?
Title: Re: Reaction conditions
Post by: smdelgado on January 09, 2020, 10:52:36 AM
OK think I got it with some help from your hint. The reaction can be performed in aqueous solution with sulfuric acid catalyst. Does that sound right?

And no, I'm not a college student. This is a small piece of a pretty large and difficult problem set of interview questions. The questions are open book, open-world (we can reach out to anyone) and range in topics from math, engineering, biology, chemistry, you name it. Thanks for the *delete me*
Title: Re: Reaction conditions
Post by: AWK on January 09, 2020, 11:10:57 AM
Bad association. This isomer can be obtained according to the anti-Markovnikov mechanism. This is quite advanced organic chemistry.
Title: Re: Reaction conditions
Post by: mjc123 on January 09, 2020, 12:28:16 PM
Mark/anti-Mark? This isn't an addition - count the carbons!
Title: Re: Reaction conditions
Post by: hollytara on January 09, 2020, 12:49:41 PM
Good catch by MJC - the chain is shorter in the product....
Title: Re: Reaction conditions
Post by: sharbeldam on January 09, 2020, 04:01:17 PM
Indeed good catch! maybe ozonlysis and reduction...
Title: Re: Reaction conditions
Post by: smdelgado on January 09, 2020, 07:43:22 PM
Thanks all!