The Other Fieser and Fieser Text

Last night, I was killing some time while waiting for a particularly stubborn 13C-NMR experiment to run by browsing through my company’s library.  I came across something particularly interesting there; everyone knows Fieser and Fieser’s classic Reagents for Organic Synthesis, but did you know before that series was published, the duo authored a first-year organic chemistry text book?  That’s right, I found an original 1950 edition of Louis and Mary Fieser’s Textbook of Organic Chemistry.

It’s got some really beautiful illustrations, and some discussions you’d probably not find in a more modern o-chem book.  I thought the readership here might appreciate some of the artwork:


The cover, complete with debossed gold lettering

pub page

We open with electron shells:

electron shells

Argon was represented by “A” until 1957

Soon, we are met with a discussion about the structure of benzene.  Correctly ascertained in 1865, the Fiesers present a short history of alternative benzene structures:

benzene structure

Structural elucidation was a laborious task in the early-to-mid 1900’s.  FT-IR was only just discovered in the late 1940’s, and it wasn’t until the 1960’s that is was widely available as a characterization tool.  Without mass spectrometry and NMR, chemists had to rely largely on elemental analysis:

CH determination

A CH combustion analysis apparatus

The principals of stereochemistry were known, and optical rotation could be determined using a polarimeter.  Chemists were still a ways off from the digital polarimeters used today:


The text describes a method for hydrogenation of olefins at atmospheric pressure in elegant style:


And distillation:

distillation app

Next up, my favorite part: a short section on explosive chemistry.  Although those picrates land squarely in the category of things I won’t work with:


And did you know that the first chemotherapeutic agent was an organoarsenic compound?  The text describes the synthesis of arsphenamine, a treatment for syphilis in the early 1900’s, until it was supplanted by the much safer and more efficacious penicillin.


And check out these subsequent illustrations of steroids and the heme group from hemoglobin: