Talk:Benzylideneacetone
Latest comment: 14 years ago by T.vanschaik in topic Grignard Reaction
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Grignard Reaction
editQuote from the article: "Treatment of benzylideneacetone with the Grignard reagent methyl magnesium bromide followed by acid-induced dehydration gives 1-phenyl-1,3-butadiene."
- In my opinion the compound 2-methyl-4-phenyl-buta-1,3-diene is formed, puting the substituents alphabeticaly en placing an as low as possible number as soon as possible in the name.
- In reference 3 the formation of 1-phenyl-1,3-butadiene is published, but I cannot find anything about "Benzylideneacetone".
Assessment comment
editThe comment(s) below were originally left at Talk:Benzylideneacetone/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.
| The article is in error. The sentence "Treatment of benzylideneacetone with the Grignard reagent methyl magnesium bromide followed by acid-induced dehydration gives 1-phenyl-1,3-butadiene.[3]" is incorrect. The reaction of the Grignard reagent with Cinnamaldehyde, not Benzalacetone, followed by acid-induced dehydration gives 1-Phenyl-1,3-butadiene, as is shown in the cited article. The reaction of this Grignard reagent with Benzalacetone would actually give a mixture of the products resulting from 1,2-and 1,4-addition to the substrate. Addition to the carbonyl followed by dehydration would give 1-Phenyl-3-methylbutadiene. Conjugate addition gives 4-Phenylpenten-2-one. 66.43.171.250 (talk) 19:47, 23 April 2008 (UTC) |
Last edited at 19:47, 23 April 2008 (UTC). Substituted at 09:28, 29 April 2016 (UTC)