The New Clayden pp. 1 – 42 && First Thoughts

Three general points before proceeding.

l. There should be an errata page on the web.  Correcting known errors with each new printing (as did Anslyn and Dougherty) isn’t fair to earlier purchasers.  For more on this see —  Software companies release patches, and just about every math book published in the past 10 years has an errata page.   Chemistry books should as well.

(Added 8 May ’12) — I have it on very good authority that there will be an errata page.  It isn’t up as of this date.

2.The book is clearly written for the budding chemist, not the pre-med.  However, it is certain that a few plucky pre-meds will read it (or be forced to).  So as the occasion arises, advice, anecdotes, cases, real life experience, relevant medical background primarily for the pre-med will appear in these notes (e.g. see the note on p. 5).

3. The 3D animations are incredible, and will certainly make learning organic chemistry easier.  Perhaps this is why I did well in it.  I could always visualize molecules in my head and move them around and look at them (not strychnine however).  Often the diagrams we draw are wrong.  Adamantane as usually drawn doesn’t look spherical, but it is.  The animations that I comment on can be reached on the web by substituting the page number I give for xx in the following.

I think this will probably increase sales of the book if people start looking at them.

Now on to the meat of the book.

p. 5 “any cocaine at all may make you a slave for life.”  Well it might, but just how likely is this? The statment is reminiscent of the great W. C. Fields movie “The Fatal Glass of Beer” — rhetorical overkill.  Millions have taken the stuff at one time or other and the vast majority aren’t slaves for life. FYI, I’ve never (knowingly) taken any mind benders other than alcohol, knowing what I do about neuropharmacology (I used to lecture med students about it). 

Even so, I’ve certainly have had to deal medically with disasters  caused by cocaine.  These include intracerebral hemorrhage from too much at one time shooting up blood pressure and vasculitis from contaminated injections.  The absolute worst was massive hemispheric stroke due to a fungal embolus and death in a 19 year old first time user from a dirty syringe  — to this day, I can’t listen to Pavanne for a Dead Princess without seeing this beautiful young woman lying there taking a week to die (due to massive cerebral edema from the stroke).

p. 5 — As a neurologist I’d like a literature reference on cis-9, 10 octadecenoamide — never heard of it, and should have. 

p, 6 — On this side of the Atlantic, Resveratrole doesn’t have an e at the end.  The beneficial effects of Resveratrol have been only found in experimental animals (mice).  Any effects in man are pure extrapolation.  That didn’t stop Glaxo, a company that should have known better, from buying a company founded David Sinclair, a Harvard biologist to use resveratrol and compounds like it for 720 million (US) 

p. 6 — “Knowing how molecules behave and how to make them is a skill in demand”. This should be taken with a lot of salt.  It certainly isn’t true in big pharmaceutical companies (aka Big Pharma), which are laying off organic chemists right and left.  For 20+ reasons why see

pp. 7-8 — Great stuff.  Good to know that the product is full of natural goodness with no nasty ‘chemicals’ in it.   The person intending to be a chemist can have a good laugh and get on with learning the science.  The pre-med had better consider the fact that they will be dealing well over once a week with people who believe stuff like this.  These people want only ‘natural vitamins’, laser accupressure, homeopathy, and certainly ‘no chemicals’.  The budding doc had better figure out a way to deal with stuff like this, both internally and externally (without causing the patient to flee).  I suggest playing a lot of poker, for practice in keeping a straight face.  When asked about these matters (say chiropractic or alternative medicine) try “that’s a theory” or “it has its place (without mentioning where you think that place actually is).  

p. 12 — “The language of organic chemistry couldn’t be simpler: it’s all pictures.”  Well maybe to us, but computational neuroscientists have spent the last 50 years trying to figure out how our brains make object perception ‘simple’ for us, and so very hard for computers.  They’re far from finished.

p. 16 — The first of the interactive web pages.  The ability to rotate a molecule in 3 space and look at it from any direction you wish is incredible.  I’m sure future generations will be quite used to this and not regard it as anything special.  However, one is rotating only a single conformation.  Probably conformational rotations will be found in later diagrams.  If you have time, take a trip to the library and look at an old organic text — I used “English and Cassidy” back in 1958 “Principles of Organic Chemistry”  The first 3 dimensional picture of a molecule appears on p. 3, the next on p. 55.   Nonetheless, Lowry, Voet, Richardson and Landesberg didn’t do too badly taught this way. 

p. 18 — Probably too early to bring it up, but the significance of the ‘kinks’ in lineoleic acid produced by the double bonds, is that they make neat side by side packing of the long carbon atom chains impossible.  This is one of the things which keeps our biologic membranes fluid.  Cholesterol is another (showing that not all cholesterol is bad).

p. 22 — Interactive structure of polyEthylene.  Nice to see spacefilling models as well.  The last picture of amorphous polyethylene chains moving around in 3 space, begins to give you a picture of what must be happening inside our cells, as proteins move about (although most of them are more compact).

p. 23  — Showing that correlation is not causation, the curve showing the decline in atmospheric lead (due to the phasing out of tetraethyl lead) can be superimposed (nearly) on the decline in SAT scores (before they were normed up).

p. 25 — The 3d model of strychnine is great — I’d never been able to visualize what the damn thing looked like.  P. S.  Where can you by a decent set of molecule models, particularly the wire ones which show the backbone where carbon atoms are seen as changes in direction of the backbone?  This would correspond to the ‘display skeleton’ option on some of the interactive structures.  With pictures this good, models may become unnecessary. 

p. 30 — ‘sodium ion metabolism’ — I think most people think of metabolism as a change in the structure of something due to a chemical reaction.  ‘Sodium ion physiology’ would be a more accurate term.

p. 30 — The structure of nitrazepam is incorrect.  The methyl group should be replaced by hydrogen. 

p. 31 — Ah laetrile: true enough that it was ‘developed as an anti-cancer drug.’  But the story doesn’t end there.  It simply doesn’t work, a fact which didn’t stop the unscrupulous from promoting it as a cancer cure.  The pre-med reading this book is sure to find similar ‘cures’ and ‘practioners’  in his/her career, as long as there are desperate patients that current medicine can’t help.  The practicioner in this case was the national arm wrestling champion who netted at least $500,000 from making and selling the stuff.  Google it. 

p. 34 — ‘Systemic names for compounds — they fill several desperately dull volumes’  — I like that.  However, the unitiated should know that many regard chemistry that way.
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  • Not Me  On May 7, 2012 at 5:43 pm

    I am not a scientist of any sort, but I certainly enjoy reading your posts here and comments elsewhere. Thank you.

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