Friedel-Crafts Acylation of Ferrocene - an Inquisitive Lab Demonstration

[@johnblacksuperchemist2556]

ANSWER at 0:46.............My guess is the H3PO4 protonates the carbonyl oxygen on the acid anhydride and forms an oxonium ion which is resonance stabilized between ALL THREE oxygens which really activates the carbonyl carbon. Also the alkoxy group on the benzene is an EDG so it will activate the ring making the benzene ring even more nucleophilic and will attack the activated carbonyl carbon on the acid anhydride doing an acyl transfer and forming the product

[@johnblacksuperchemist2556]

ANSWER at 1:00 ..........The 3rd molecule would be the major product. The FIRST carbonyl attached to the benzene ring is a EWG and will deactivate the ring. So the 2nd acylation will be on the other benzene ring. ALSO because the carbonyl is EWG it is a meta director. And in example molecules 1 and 2 the groups are added ortho and para

[@johnblacksuperchemist2556]

QUESTION.........Why are you using gentle heat?????????? For alkylation i thought it was always done in the cold. Are you heating cause your are doing an acylation instead of an alkylation??????? Or are you heating because you are not using the best catalyst and electrophile?????????? Cause i know ethanoyl chloride would be more reactive than an anhydride for acyl transfer or really for any reaction probably. Should all friedel crafts ACYLATIONS be done with some heat instead of cold???????????

[@chemprofdave]

No audio, right?

[@ChemistryConnected]

Your speakers are not broken! Your question is a good one, though, so let me explain my choice. Without audio, instructors can use this video in a number of different ways. A student can watch it and record observations, like they would in a normal lab. In a typical lab, no one would be explaining the procedure to them as they go along. Other than using their hands and physically being in the lab, the expectations for completing a pre-lab assignment, keeping a lab notebook and submitting a lab report can be the same as usual. If desired by the instructor, answers to the embedded questions can be included in the observations, or as a separate report. Otherwise, they can simply serve as a reminder of the decisions that need to be made throughout out the procedure, and questions of this nature can be included in a separate assessment (e.g., lab final). Another option is to watch this video synchronously with your students, via videoconferencing. The video can be paused at each question to give time for a poll and a discussion. (As anyone who has used clickers in their lecture knows, the poll results can be very surprising!) This approach enables the sort of one-on-one mentoring an instructor can provide to their research students, or if they had unlimited time (and maybe access to a dozen clones of themselves) in a traditional lab setting. Viewing the video with your students provides an opportunity for students to ask questions and clear up those persistent misconceptions. With this approach, formative feedback is provided, and comprehension/retention can be probed at a later time with some form of assessment.

[@chemprofdave]

That’s what I was thinking, though without the pedagogical detail. 🤓

[@doyale2]

Very nice and educational video! I would have loved to also hear some audio though.

[@Learnest]

Very informative video maam. Do the bubbles form due to release of CO2 from the Bi-Carbonate?

[@ChemistryConnected]

Sounds good! Check out this cool demonstration that provides evidence of CO2: kzbin.info/www/bejne/m6CognmiaJd4bc0

[@matteomoioli5210]

Great video !