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Topic: synthesis question  (Read 5228 times)

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synthesis question
« on: May 03, 2004, 04:14:25 PM »
Hi, I am in Organic Chem at the University of Wisconsin-Madison.  I'm not sure how to name the compound, but we have to synthesize acetophenone with 5-methyl-2-hexene attached in the para position on the ring at the 3rd carbon in the chain.  We have to synthesize it from bromobenzene and can only use inorganic reagents or organic compounds with less than 6 carbons.  I have figured out that I can use F-C acylation to attach the acetyl group, but I am not sure about how to attach the chain, and how to add it on in parts so that I am using 6 or less carbons, since there are 7 carbons total.  If anyone could be of any help I'd really appreciate it!

Offline hmx9123

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Re:synthesis question
« Reply #1 on: May 04, 2004, 01:26:23 AM »
Just looking in the Merck Index, it lists for acetophenone:

"Made from benzene and acetylchloride in presence of aluminum chloride; catalytically from acetic and benzoic acids.  Prepn from benzene and acetic anhydride: Adams, J. Am. Chem. Soc., 46, 1889 (1924)."

This reference is for the Journal of the American Chemical society, volume 46, p.1889, from the year 1924.  The chem library at Madison will have this journal on the shelves if not on line.

Your specific compound is out in the literature somewhere, so if I were you, I'd take a trip to the chem library and have the clerks help you use Sci Finder or Beilstein to look this compound up.  Although the theory behind how reactions work may get you somewhere, there's probably a chemical procedure already out there somewhere for making this compound, and all you'd have to do is follow it.  Since this is an educational lab, you might also want to look through the Journal of Chemical Education, because many times labs come nearly directly from that journal.
« Last Edit: May 04, 2004, 01:29:00 AM by hmx9123 »


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Re:synthesis question
« Reply #2 on: May 05, 2004, 08:20:27 PM »
thanks for your *delete me* ;D

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