I've been a bit under the weather lately. Nothing serious and nothing 4 mg of loperamide HCl couldn't fix. I wanted to blog about the cyclopentene post I made, but I haven't gotten around to it.[1] Now I'm feeling better.[2]
Enough about me. Let's talk about the dehydration of cyclohexanol. As it turns out, I probably should not have been too surprised at the results. From the comments and an email I got from my brother including an attached paper from Industrial and Engineering Chemistry Research[3] it is clear that the formation of methylcyclopentenes during the acid catalyzed dehydration of cyclohexanol is entirely reasonable.
In hindsight, I should not have been so surprised. Before divulging my ignorance to the world, I should have mulled it over. Oh well.
What I've learned is that having colleagues in Organic chemistry would be nice. I teach in a 2 person department. My colleagues is an Inorganic chemist. He is great at what he does, but we find it difficult to have discussions on advanced topics in organic or inorganic chemistry. Neither of us knows enough about the other's area to be any good.
I love teaching where I teach, but I miss the impromptu discussions that occur between chemists. My substitute for that is this blog. I may continue to post questions that could easily be resolved with a discussion with another organic chemist. My goal is to learn even at the risk of exposing my ignorance.
[1] I also wanted to bottle all of my beer, but I only got 2 of the 3 batches done.
[2] Sadly my 2-year old is not.
[3] I gotta be honest, I'm not a regular reader of what I'm sure is a fine journal.
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I think the suprizing part is that you noticed the 5% of Me-cyclopentene in some of the products, on GC-MS. I don't think many people would be so rigorous about a teaching lab, having a decent instrumentation (I wish we had a working GC/MS here in at the institutte in Florida) or would investigate - or admit that they don't know.
Now you can use this piece of information when you teach about Meerwein rearrangements of carbocations.
Also, give your little one a lots to drink (preferably some Powerade or other sport drinks that contain some electrolytes). People survive things like cholera on their own - but it is the dehydratation and salt disbalance that does them in.
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