The end of casual leafing

This morning I received the E-mail from the Organic Division of ACS informing the membership that we will no longer receive the annual Organic Synthesis paperback at part of our membership.  I knew it would happen sooner or later, but I still felt a sting.

No mater how hard we try, keeping up with the literature is always a challenge.  Each year when Org. Syn. would arrive I would put it on my "leafing pile".  This is a pile of stuff that I leaf through when I have a few moments to kill between meetings or that I take for plane trips.  Back in the olden days this pile included paper journals, but my access to those went digital long ago.

Leafing is a great education.  I would catch chemistries that helped in my research or gave me new research ideas.  It helped me recognize new conceptual and experimental trends in the science which I would then make a point to read about.  To the extent that I keep my knowledge of the latest organic science fresh I attribute a good bit to leafing through journals and looking at papers that I would never have looked at based on a title or graphical abstract.

I guess I need to find new ways to keep up and watch for trends.  Thankfully, in the mean time my annual copy of Annual Reports in Medicinal Chemistry arrived last week from the ACS Med. Chem. Division.

T.S. Hall

Research on a Budget

In addition to my unexplainable curiosity about mechano-chemistry (which includes sonochemistry and grinding or ball-mill reactions, none of which I do), papers that key on low cost research tend to catch my eye.  I suppose it's because my group runs on a shoestring.  With this in mind, I will draw attention to a recent Tetrahedron Letters paper on the use of animal bone meal (ABM) as a catalyst of the crossed-aldol condensation.  This is actually the second paper from this group, but I don't have access to Letters in Organic Chemistry papers, so I missed the original report.

In the recent paper, the authors did not go into the conceptual leap that inspired this research area, which I am curious about.  But, I do love how the mostly Moroccan authors spent no dollars, or dirham, with Aldrich or Acros for their catalyst.  They invest some column inches on how to prepare ABM and Na/ABM from animal bones "collected from nearby butcher shops." (Na/ABM is ABM impregnated with sodium nitrite.)  Now, that's research on a shoestring!

So, as you gaze upon the carcass of the once golden Tom Turkey upon your table give Thanks that the catalyst of a new research venture lies before you.  I can see the series of papers now; Turkey Bone Meal catalyzed . . ., Free Range Turkey Bone Meal catalyzed . . ., Wild Turkey catalyzed blog writing in organic chemistry, etc.

Happy Thanksgiving!

T.S. Hall

On-line Scandal to Come

I am currently working on creating an on-line Introduction to Regulatory Affairs course for our College of Continuing Education.  Aside from the course material itself, which I will go into at a later date, I have been assigned a minder to "help" ensure that all the university on-line content rules are followed.  In the course of my initial meeting with the continuing education folks a conversation on ensuring the security of courses ensued.

There are people who will take on-line courses for students and/or will take on-line examinations for the student.  With the increasing push toward on-line education educators need to get ahead of the future scandal when this issue comes before the public.  A widely publicized incident where a public figure or a group of pseudo-public figures are caught which unearned on-line credentials will cause a backlash that will have the public throwing out baby and bathwater.  This endangers what promise on-line education has.

One potential solution to the problem of credentialing the on-line student is to enforce identity checks in on-line testing.  This could be done through a little cooperation between institutions.  In a state like California where you can't spit without hitting a community college, Cal. State or Univ. of Cal campus there could be testing centers where the on-line student can come with their ID to take tests.  If we add in public libraries and public high schools this type of cooperative sharing of resources could actually facilitate the development of on-line education in a form where the credential actually has some value.

For those in the physical sphere of education, it should be pointed out that similar checks might be appropriate in your courses too.  As class sizes have grown, how many of us really know all our students.  I am reminded of a case from over a decade ago where a colleague discovered at the last exam of the semester that one student taking his organic course, and earning an A, was not in fact the student of record, but a family friend dentist who had been in the classroom and taking tests all semester.

I also have a colleague in the business college who checks photo ID at every exam.

I have stated it before; As the internet makes content freely available the job of institutions of higher education will increasingly become one of credentialing and training in technique where on-line learning is not sufficient.

T.S. Hall

The George Molecule

My undergraduate organic instructor and research mentor loved the nonstandard names given for organic molecules, including George, Housane, Pagodane, etc.  They bring a little whimsy into the subject.  In those days common nomenclature was the primary type of naming used in the course.  In the intervening decades IUPAC nomenclature appears to have taken the drivers seat in most texts.

This semester I have been teaching for the first time from the organic text by Jones and Fleming.  While the students really like the writing style, I have found that the use of common nomenclature is driving me to distraction.  IUPAC nomenclature is brought in, but common nomenclature is used the vast majority of the time.  One bit of irony for me is that the authors write about "bling" in talking about diamond, but still use amyl and appear to think that the name ethylene is IUPAC nomenclature.

While common nomenclature is necessary as it is still used, systematic nomenclature offers the opportunity to train the student's mind to build a body of rules that can be applied to systems they have yet to see.  It fits well into the idea of building the capability to predicting the products of reactions between reagents one has never seen.

One problem in the use of IUPAC nomenclature in text is that most of us don't know all the basic rules, so many text include errors in their IUPAC naming.  Taking a page from days gone by when there were texts on organic nomenclature, perhaps we need a primer on IUPAC nomenclature for organic faculty.  Something like a Oxford primer soft cover book.

T.S. Hall

Stop the Slaughter! Please! I'm begging here!

Perhaps I should not have given an exam the Friday before Halloween.  The students were in a particularly blood thirsty mood.  The wanton destruction put me in mind of Timur (Tamerlane) standing on a pile of the heads of his 100,000 captives during the conquest of Delhi.  It made no difference (to the students, not Timur) what Lewis acid was on the oxygen, the carbon-oxygen bond was almost always broken.

I warned the class several times about decapitation of alcohols and alkoxides, to no avail.  Appeals to consider electronegativity differences did not sway this group of students.  When asked, they remembered the picture of the decapitated alcohol, which they thought was funny.  To bad that they did not remember the concept behind it.

I often try to bring in analogies that will make them laugh to help them remember concepts, particularly those that they commonly trip up on.  The lesson, I suppose, is that being entertaining is not the same thing as educating.

So, back to the drawing board.

T.S. Hall