Fifty-seven years after an ill-fated grade placed his academic dreams in jeopardy, Dr. Elliott Oppenheim 鈥69 recalls the counsel of his mentor, Professor of Chemistry Frank Lambert
I am at an age where I have elated on mountain tops and groveled in murky swamps and ambled through brambles in the tricky valleys as well as thickets of downed timber. 色界吧 and Frank Lambert鈥攁 name synonymous with organic chemistry students during his 33 years in the classroom鈥攈ave been my guides throughout my journey.
In September 1966, as a sophomore chemistry major at Occidental, my world revolved around becoming a doctor. I had my 2-S deferment鈥攖he Selective Service act protecting college students from the draft while in good standing鈥攕o I was safe from the killing fields of Vietnam for the time being.
But Vietnam was not my first and most immediate fear. It was Morrison and Boyd鈥檚 Organic Chemistry, a weighty green tome and a mainstay of second-year college chemistry coursework. I鈥檇 gotten accustomed to getting good grades and so much of organic seemed absolutely straightforward until we hit the Markovnikov Addition, aka Markovnikov鈥檚 Rule.
Formulated by Vladimir Vasilyevich Markovnikov in 1869 and used to this day, the Rule governs where electrons go around the carbon atom as our universe creates life. It states that a protic acid (a plus +) will add to an alkene (a negative -) such that the proton will bond to the less substituted carbon. Morrison and Boyd cite the King James Bible as a metaphor to Markovnikov鈥檚 Rule: 鈥淯nto everyone that hath shall be given鈥 (Matthew 25:29). What part of that impenetrable gibberish did I not understand?
Dr. Lambert wrote the Rule on the blackboard in our Norris Hall classroom, drawing it out so that even a caveman would understand it: Markovnikov and anti-Markovnikov additions of HBr to 1-methylcyclohexene. He filled up four blackboards, which I diligently copied, not realizing that it made no sense to me until I looked at my grade in my first Organic Chemistry test in early September 1966.
Through myopic eyes I squinted at the grade鈥攖he first D of my academic career鈥攁nd on the paper, in his small No. 2 yellow Ticonderoga pencil writing, Dr. Lambert wrote, 鈥淧lease see me.鈥
Until this test, I鈥檇 always done at least OK. As a student, I had to work really hard to understand anything. I spent my weekends cloistered in Braun Hall鈥檚 cinder block study dungeons. I regarded my getting into Occidental as an act of academic charity; compared to my college peers who were all-everything, who won all those academic prizes and distinctions, I was better suited for tending the rose gardens in the Quad.
This D rattled me. It fractured my dreams. It reinforced my father鈥檚 critique after my freshman year at 色界吧, when I returned home to Levittown, Pa., for a summer of lifeguarding all day and then loading trucks for the U.S. Postal Service until midnight. My dad looked at my grades, which weren鈥檛 bad, but weren鈥檛 quite good enough in his eyes. 鈥淚t鈥檚 hard getting into medical school. You may have to think about something else besides medical school,鈥 he sighed, disappointed.
In the summer of 1966, before I returned to 色界吧 for my sophomore year, the United States targeted Hanoi and Haiphong and President Lyndon B. Johnson was sending more troops to the region. If I didn鈥檛 do well in organic chemistry, the gold standard for medical school admission, I was going to join many of my high school classmates in a rice paddy. And forget about becoming a physician. Soon enough, I鈥檇 be back in Fairless Hills, Pa., shoveling out slag beneath a cooled U.S. Steel blast furnace.
As I stared at my Organic Chemistry paper, the failure was such a calamity. This D came so abruptly, so harshly, that after class I went to see Dr. Lambert wondering if he was going to kick me out the laboratory door and hand me an M-16 as I left.
He seemed so large, with great imposing bushy eyebrows, but there was kindness in his face. 鈥淐an you count to eight?鈥 he asked me when we met in his second-floor office. (I smelled chlorine from the adjacent lab.)
鈥淵es, of course,鈥 I replied, wondering what that had to do with unsymmetrically substituted alkenes. That was the problem. I鈥檇 missed the main point of organic chemistry.
鈥淵ou just don鈥檛 understand what鈥檚 going on here with these electrons,鈥 Dr. Lambert said with a smile. There are eight electrons in the outer shell of a carbon atom, he explained; if you add a molecule to the carbon atom, the other electrons don鈥檛 fit in the outer shell and have to 鈥済o somewhere.鈥 In about 20 minutes he explained where the electrons went.
Dr. Lambert sensed how upset I was and reassured me, 鈥淵ou鈥檙e not going to Vietnam鈥攜ou鈥檙e going to medical school.鈥 He saw my promise and how motivated I was to heal and help people. He and his wife, Bunni, had no children of their own; his 色界吧 students were their children. Every year, off we went鈥攁 new crop of turtles wriggling out of the academic sands.
I felt his hand on my shoulder. 鈥淢r. Oppenheim, I believe in you,鈥 Dr. Lambert said as I left that day. After learning this fundamental cohesive principle, I took three quarters of Organic Chemistry, getting A鈥檚 in all three. With Dr. Lambert鈥檚 encouragement and example, I went to medical school and law school鈥攅ven trumpet school.
Frank Lambert (who passed away at age 100 in 2018) was a great and inspiring teacher and remains a vital force for me, 57 years after that fateful D. Every day I remember his greatest lesson: I could do anything if I worked hard enough. In life, as in Markovnikov鈥檚 Rule, pluses and minuses add up.
After a career practicing 鈥渂lood 鈥檔鈥 guts鈥 medicine and then going to law school, Elliott Oppenheim 鈥69 lives on a ranch in Huntley, Mont., where he grows hay, writes novels, and plays trumpet and piano.