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The time, twelve minutes before the end. The date, Monday, October 19, 2009: the second midterm for the “weed-out” class for pre-meds. One simple nickname: Orgo. Its very evocation, ironic – Organic Chemistry being the field of plastics after all – struck fear in us students. The event, this:

Number 9 (12 points): Draw the reaction product(s) of 1-methylcyclohexene with 1) BH3 and 2) NaOH, H2O2. Depict the entire reaction mechanism of this reaction sequence.

Where in the world had this come from? I furrowed my brows, could sense heavy sweat beads forming over them, about to cascade. My nape was starting to hurt from remaining in the same bent-over position for so long. I looked up and around, twisting my neck about to try to ease my strained muscles. Up front the professor walked from hand to upraised hand, bending over and whispering help and hint, while those nearest put down the pen and listened.

I lifted my pen to the page, then stopped. The moist air hung with the heaviness of sweat and clung to my skin. I couldn’t start on this question. My pals Ben, Jack, and Chris were apparently having the same problem. Seated two seats to my right, Jane flipped over the last page and began going over the test again, face smug. She was a page-turner. Come to think of it, she almost always looked at ease on any test. Those sharp eyes surfed across the page, and her ball-point pen danced, tracing runes, C, H, and O.

She was the most learned person I knew, and knew the answers to a lot of the Jeopardy questions. When we first met this year it was still January, when we first clasped hands we had each aced our first intro-to-chemistry exam of the spring semester, and when we first kissed is for us to know. From then on we were practically always together, and when we weren’t we would trade a thousand text messages a month. I remember one day that summer when the skies kept clear and the moon waxed bright. Standing on the moonlit lawn of my suburban two-story I gazed at the stars, with a Nokia by my ear. It was Jane, and my recall isn’t great, but it went something like this.

“Hey Martin look outside. Isn’t the moon lovely?”

“Yes, and I think I can see you in it.”

“Well, just wait until your flight back. I’ll be there waiting for you.”

“I’ve been studying Orgo lately, and I can’t help but feel increasingly worried the more I read. I just don’t get it,” I said.

“Sounds like you’ve already got a head start on everyone else. Don’t worry. We’ll study for it together.”

From that day on I spent some time every day just wishing for school to resume so that we’d be together again, even if it meant that Orgo was getting closer.

Soon the nightmare had arrived. I lived all the way on the far side of campus. While Chris and the others partied and played beer pong down the hall, I would often study alone, since I couldn’t let Jane outperform me again. That had happened way too often, and I was beginning to doubt if I could continue to live with myself being this useless. My B in introductory chemistry paled in contrast with Jane’s A. Among us pre-meds, that was a world of difference, and we always kept an eye on our GPA. I wonder what she thought of me. She would often come by to my room and help me with my work, so she must know that I was doing my best. But was that even a good thing if I didn’t succeed? I was pretty sure Jane liked me not for my grades but for who I was, being hardworking and all, but this college had its fair share of diligent students who also turned out to be successful, and any other number of adjectives.

I reminded myself of this when I usually do: as it gets late into the night. The skies outside had changed from the pink and orange of sundown to the naked void of a cloudless midnight sky. When was this, two or three weeks ago? I can’t remember – all these study sessions blurred together.

On the bed opposite mine Mark tossed and turned as he usually did, unable to sleep. “Martin, what do you see in that book of yours anyway?” he had said on the first day of school, but no longer.

“Don’t you see I’m studying for Orgo?” I had said, and Mark shut up.

My laptop was probably playing a soundtrack, of which songs I don’t know, just that it was a composite of lively jazz and classicals. It was good for keeping one awake. A square table five feet on a side stood in the middle of the room. We huddled over our books, I forget what page I was on, one arm propping our tired heads on the table. We forced our eyes across the glossy text, till tears and dust motes clouded our vision and the words floated off the page.

The night had leached away the warmth. Jane was wearing a cotton sweater, and I a tee-shirt. She leaned a gentle hand on my shoulder, and when that didn’t suffice, pinched. “Hey, wake up.” I wasn’t listening, and for punishment she pulled out a strand of hair, a white one, dangling it before my wide-open eyes with a mischievous grin. “You’ve got to keep studying no matter how tired you are.” Well, I knew that already: they say your Orgo grade is the fifth thing they look at, after MCAT, GPA, volunteering and interview performance. I rubbed my eyes for the umpteenth time. “Go ahead, you can keep your eyes closed. But try to imagine all we’ve just learned, floating around. See if you can picture them in motion.” I sank down on top of my book, using my arms as pillows. Silently, she took off her sweater and draped it over my back. It was coarse, though very warm.

I now tried what Jane had suggested. I closed my eyelids, plunging myself into a world of darkness, with only the eerie, dim glows remaining. In my mind’s eye a dozen or so molecules appeared, a golden one for each hydrogen, white for carbon and red for oxygen. Perhaps it was my overactive imagination, but were they holding hands and dancing? The atoms parted hands and found new dancing partners, and now I recognized my teacher in this memory, looking as always like today was a bad hair day for him, with a plain beige coat, well kempt, droning on with a tinge of Midwest dialect.

Pen in hand, I began scribbling down what I could remember. On the blackboard – this must have been from six or so lectures ago, the memory was so dim – the lines of chalk depicted what I needed to know, but stopped prematurely. As I recall, the professor started writing out this reaction, at least the first part, but he didn’t finish it. Ben, Jack and all the rest were scribbling down anything and everything like they were the word of God. I probably was too. Straight from the horse’s mouth. Only later did we learn that not everything we learned was true. Lewis structures? Exceptions everywhere. Pure products? Scratch that. Theoretical yield? You’re a god if you can get even 70%. IUPAC naming conventions? Real Orgo chemists make up names – like buckminsterfullerenes.

A red and black polyester jacket, a light one good for the fall, covered my lap. I clutched my right hand. These knuckles were bared white, with the blood drained out of them. I rubbed my toes against abrasive socks and the tongues of my Nikes: cold. Keep frosty, I told myself. For a moment I couldn’t remember what the next part of the answer ought to be, so I let my eyes wander. In the seat in front of me Ben was staring at his modeling kit again. Then he spun the plastic skeleton about between thumb and index finger, back and forth.

I never could understand what Ben was doing at times like these, but whatever it was, it earned him an A- on the last midterm. He was a good tutor too; between him and Jane, I resolved a good three quarters of my concerns. “You’ve got to be able to extrapolate,” he once advised, and he was right. If I had listened I probably would not have stopped at learning just the first half of the reaction.

Ben had the most surprising inspirations. Once, three or four weeks into the semester, we went to the teacher’s office – not difficult to get to, really, his office suite was right down the hall from Love, the first door to your left, if you get to the rooms with all the computer equipment you’ve gone too far – and then and there he asked a question about ethers, and voila! the question showed up on the first midterm, out of the blue, to us essentially free points, like manna falling out of the sky. In retrospect it seemed that I only succeeded on that one through sheer luck, and through the blessings of my family when they call me the night or the morning before each exam. “Good luck and do well,” they’d say, “Your grandmother bids you good luck on your test.” How they managed to drag my grandma into this I have no idea; last I recall she was living in Australia.

“Thank you, and I will,” I’d say. I take my promises seriously. These last few months I had spent every free moment wallowing in the facts in my textbook. I explored every nook and cranny of the academic battlefields named stereochemistry and reaction mechanisms. I withdrew from society. Clubs, anyone? Not for me. Edens dorm activities? Don’t have the time. How about free food? Is this one of those events that I can send my roommate Mark to get them for me?

Now this may seem like I’m addicted to studying, but it wasn’t just me who was studying hard. Last year I got to know a bunch of other pre-meds from general chemistry class and we decided to apply for our current semester’s dorm rooms as a single bloc, and that’s what we did. Parties in our hall got cancelled for the week before each of the three Orgo midterms, and everyone knew the dates because they were posted on the local bulletin board, set in a sheltered part of the stone wall, right next to the words “Quiet – No exceptions.” Tacked beside this calendar, up to a hundred event flyers vied for attention, their words promising escape from the tedious life I led.

But I studied harder than the rest. Weekends saw me poring over lines of esoteric writing, then reading between the lines till words made of impossibly bright light started appearing between the lines of text whenever I opened the book and even when I set them down. Friends stopped calling me, and people around me began to be replaced by strange faces. On weekends either Jane or I would bring back a dozen meals from McDonalds, always the same kind, and we’d keep them in the fridge. I know it’s kind of gross, but hey it saved me some time. Orgo lingo spilled from my mouth, with jargon like gauche and chiral and steric hindrance for awkward and handed and got in the way.

I worked so hard and kept at it for so long because I had made myself a promise from the very beginning. A patch of woodland, really an lush, unkempt garden paved with dark-grey gravel, lies on the path by our dorm. Many times have I paused there to reminisce on my promise, breathing long and deep in the fresh September air, beside the firs and the weeds and the wild bushes. I stop at the same place, grinding the little stones underfoot, at the same time, every Monday, Wednesday, and Friday before and after class. It’s like I have buried an ancestor there, as if I had placed his photo on that tree stump. I tell him of what I have done, and will do, to study for this class, and he gives me his silent blessing. We hail from a long line of non-doctors, or so my parents tell me; they have never been rich. That was a goal for me to aim for, they’d say. Thus they told me, and so on my first trip to Love one chilly and overcast Monday morning, I found there a stretch of bush and crab grass that rarely comes under the feet of passersby. I had sworn then, to whatever deities lingered in that reinvigorating, crisp and thin air: one day the red carpet of medical school shall unfurl before me, and no mere piece of paper, no simple set of instructions could stop me.

This thing before me was starting to get in my way. Ben stopped fooling with his cyclohexane model – he must have realized that we’ve seen this problem before, and he beset his foe with a vengeance. He didn’t stop writing for a good minute or so. I wanted to see what he was doing, but then again I knew better than to cheat. This was a little feud between me, my dreams and the little devil that was getting in between us. I was going to solve this question on my own, no matter how long it took. What was it Ben had remembered though?

The last time all of us studied together was just at 2 AM yesterday. All the good study buddies of mine had come: Ben, Jack, and Chris, and my girlfriend was ever-present. Aside from her, we all had dark smudges under our eyes, the kind you get from taking some serious but boring task as seriously as you should, and half the time my vision blurred from my eyelids wanting to fall down. I couldn’t really pay attention to what everyone was saying. Awash in the aroma of beer, Ben, who lived in a generally raucous triple next door, brought over a few cans of Red Bull, enough to go around. That was my first taste and kept me awake for quite a while. Jack, who lived in an adjacent dorm but shared my lab session, had a mug of hot coffee with what I think was a brown Java logo on it. He would take out his pen and write something every once in a while, but the back of that pen was most often in his mouth being chewed upon.

We sat cross-legged and studied on the rough, mottled olive carpet of my room, a growing pile of disregarded trash building up in one corner, topped with the box from that night’s Papa John’s pizza. Our Orgo textbooks were laid out before us, deflowered with page-folds, highlights, underlines and the occasional dent of graphite, the casualty of absent-minded pen-twirling. We took turns shooting each other questions. To keep everyone alert we passed around Mark’s Rubik’s Cube, which Jane could solve in thirty seconds flat and which she had given up teaching to me – I couldn’t even begin to memorize the patterns. When not playing with the cube, Jack generally hid one hand tucked up in his parka. He spoke in a soft, stuttering voice and asked the fewest questions and I generally ignored them anyway.

Maybe I should have paid more attention. Jack had asked, I think, this wee little question about how the something-or-other was involved in this reaction for, as he said, “It doesn’t even make any sense.” He phrased it with such an unassuming tone that I could not for the life of me imagined that it would ever become important. I couldn’t remember the book’s ever mentioning it, and I thought that was enough. Besides, Jane, who one could always expect to be the first to offer an answer to everything we asked, was also, you’d wonder why, shooting us the hardest questions one could think of, half of which Ben would try to answer with help from his molecular model kit and the other half of which he dismissed, with a nonchalant yet flushed face, as being good questions but certainly off topic. The impression of irrelevance must have carried over – in hindsight, a big mistake. Heaven knows it wasn’t my fault; I was sleepy by then, very sleepy, after four hours of nonstop studying, a trip to the restroom before that, which was already after another four hours of Orgo.

Now I traveled back in time, but everything there was ghostly, elusive, and unresponsive. Everything I tried to recall carried with it a tint of sepia, and it was all black and white. Jane was helping the other me, but with what, I could not remember. In the middle of the table was a vast sheet, nine pieces of plain paper scotch-taped together at the seams, a little diagram in the middle with an explosion of arrows leading away from it in all directions, reagents and products and reaction names and electrons being shoved around. Ben was explaining to Chris the SN2 mechanism we just recently learned. I think the conversation went something like this:

“The SN2 involves a nucleophile attacking the main molecule from the only point without steric hindrance, ejecting out whatever substituent was on the other side of the attacked carbon.”

Chris said, “Oh, so it attacks from behind, right?”

“Cut it out man, we’re trying to study here,” said Jack.

“Actually, that’s a rather nice one,” said Ben. “One major reason why so many students have trouble with Orgo come second and third midterm is because of the confusion between SN1 and SN2. Think of it this way. SN2 is my love life to date. When I first met Erin, she was seeing someone else. But I had better grades, knew some of her friends well, and we knew each other for a long time now… I was the stronger nucleophile, so I gradually displaced the other guy, and as I got closer and closer to Erin, he became more and more detached. Course, along the way the situation was a bit tense. And there you have it, SN2 in a nutshell. Contrast with Martin and Jane, a classic SN1 reaction.”

Jane looked up from her laptop. “Shut it. We’re a synthesis reaction.”

I smiled, and Ouch! I bit my lip. There was nothing to take away from this. Was I going to fail? I looked back at what I had written, and suddenly inspiration hit me. One of those Ben moments, I’d think, pulling a brilliant idea out of your ass like that. “Attack from behind” on the oxygen wasn’t your typical SN2, but it worked. Now if only my memory wasn’t so bad, so that I could recall the rest of it. I could sense the impending victory. I was close, only one or two steps away from the answer.

Six minutes. The anxiety level in the room was rising. I could hear the sound of many pages flipping back and forth. Were the last questions that easy? I flipped to the last page, frowned in dismay at some complex steroid molecules, and flipped back. Jack was now scribbling away too, though he paused often, and Chris, to Ben’s left, scratched out a failed answer.

I shifted in my seat as it was getting uncomfortable down there, even though the warm, red fabric itself was not at fault. Yet another excuse for getting distracted. Ben would finish soon, flipping through, checking answers here and making corrections there. Jack sat there, eyes staring off into the giant presentation panel above the blackboard ahead. I don’t know what he saw there. Maybe he could visualize with his eyes open, or maybe he was making connections I couldn’t even dream of. Everyone seems to have a secret as to how they do well on exam day.

Jane returned from having turned in her exam, walking up the steps with her imperturbable, stately posture. She sat down and wrapped some stray hair behind an ear, and now sat mute and patient to my right, head hunched over and reading a novel, Twilight. She was waiting for me, and I knew I couldn’t miss this question. I wished the test was behind me, and for the time to freeze. You’re adorable, sweetheart. I didn’t mind being turned to stone right this instant. That would mean time could stop and responsibilities would lift and agitated heartbeats would calm and this glance would go on and on and on.

The situation grew more and more hopeless by the second. For the next few minutes – seemingly hours – I played the choreographer, partnering imaginary molecules in all possible combinations and playing out the sequence of their dance patterns, but to no avail. The heat of anxiety now coursed through me. There was also that other question I skipped a while back, I remembered as my heart skipped a beat. No time for that now; I had put all my effort into this one. Put your all into it, my mother once said to me. Give it everything you’ve got, and you’ll succeed. I know you will. You’re my son.

Of course: when I was growing up, I was probably the only kid in my neighborhood that had to study almost all the time, and I had gotten used to it. It wasn’t even much of a work ethic: that was something I just did whenever I had to. That’s how I had done all right in chemistry class. That reminds me: we talked about the first law of thermodynamics, which was all about this idea of energy never being created or destroyed, only transferred. It was basically a law of equivalent exchange, which was exactly what it sounded like. It resonated with me. I liked to think that all my hard work in college was the price I’d have to pay for med school admission: work hard enough, and I’d get in.

But in our Orgo labs, Jack and I would frequently watch the beaker, flask and test tube swallow ever more ingredients, along with all our effort, only to have the beaker’s contents evaporate in a puff of steam, others sticking to the flask’s bottom, the test tube breaking. Something was lost along the way. Rarely would we get much of anything in return. Where was the equivalence then?

Would the promised exchange come now? I looked at the clock. Three minutes to go. The rustling of others’ exams were ever-worsening rumbles heralding an earthquake. The arteries of my neck throbbed, each beat pulling me away from answering that question. Prodigies, overachievers, and ordinary students, in that order, stood up and departed.

I could not stand up to leave. I had grown fat. Whatever happened to those biweekly tournaments Chris and I once held? I longed for the tactile sensation of the basketball’s numerous little bumps, the pitter-patter of paddles on ping-pong. I hadn’t seen either in months. Sweating, trying to match Chris’s quick moves, stealing the ball away from him, zigzagging across the court to dunk that in – had I really ever had such a life? All that’s left now for me to remember them by is a solitary plaque, the men’s intramural team, with all those smiling faces, sitting in a drawer under my desk where it lay buried under five inches of lifeless Organic Chemistry.

Only a handful of students remained now, not Chris, not Ben, not even John, with only Jane waiting for me. She was trying hard to not seem impatient with me, reclining in her chair with legs crossed, smiling, eyes surfing the pages, sharp and seeing. The answer remained elusive. Maybe I had squandered my time reminiscing about the past. My fingers clenched hard around the pen. I couldn’t focus. Sparks of blackness danced and jumped about my vision. I was about to throw up. Time accelerated, leaving me to watch with ever-growing horror as…

Damn it, time’s up.

Two days later when the grades came out, Jane embraced me, showing me her A+. Her skin felt warm, soft, and smooth, as were her words of reassurance when I told her I thought I might have done poorly, but that soothed me little. I was undeserving. I had given my all and still missed that question, while I was sure Jane had blown through it. Maybe I would be the one leaving as someone stronger took my Jane away from me the way Ben took someone else’s Erin. Later I called my mother and asked her to go on Blackboard to see what grade I earned on that test – I could have checked myself, but I didn’t feel like doing so. She hung up to check the internet, then called me back saying, “I’m sorry. You’d best find another career.” Really, she did. For a moment I must not have even heard her. That moment my mind wandered back to the first day of school, when I had sworn that I’d succeed in this class. Back then the rules of the game were clear: equivalent exchange. And that’s what I did: I had given, given up everything, time, effort, and friends, and I received nothing. Where’s the damn equivalence? I had done all that I could. It just wasn’t enough.


Number 9 (12 points): Draw the reaction product(s) of 1-methylcyclohexene with 1) BH3 and 2) NaOH, H2O2. Depict the entire reaction mechanism of this reaction sequence. (Hint: You hadn’t seen this before, so go figure.) Cue the evil laugh.

I grinned at the prompt before me. I grinned at every question that tried to be difficult. After all, this is Jane we’re talking about, and since when did I ever fear a test? Martin had good reason to, even Ben maybe, but I was different.

Everyone else was wracking their brains for whatever scraps of information they could remember. I meanwhile was scrolling down the Wikipedia article “Hydroboration-oxidation reaction”. Reading with my eyes closed. Suspended in nothingness, these lines of text rushed past me from right to left. They were like shimmering beads and strings of light like silk. After the words came diagrams, first a blur and then resolving to crystal clarity as I shifted my gaze to each part in turn. The images had been well-preserved. Having the internet at one’s disposal at times like these was a game-breaker, but that didn’t mean I wasn’t going to use it.

I had not studied this reaction before. Most reactions I came across I had no idea what they were. Even the most basic reactions, with atoms that could be counted on two hands, featured enough mechanisms to warrant a whole hour of lecture – and we’ve only had around two dozen hours of lecture so far this semester. God knows how many possible reactions could be classified as organic chemistry. No, I hadn’t studied this reaction before. But I had seen something similar once when I was surfing the Web. Just a glance, but it was enough.

Now I started learning this subject for the first time. In my mind’s eye I saw the molecules as white points of light before a backdrop of eigengrau. Now stay put and don’t haze, I commanded the image, as I opened my eyes, took up my pen and started scribbling down with precision every minute detail. Electron pushing, free-radical pushing, free-radical bromination… As my thoughts wandered, the image before me contorted and Technicolor streaks of something called “the propagation step of free-radical bromination” materialized in its place. Pay attention, I ordered. It took me a good thirty seconds of staring at the image I had conjured, to comprehend what it was I was looking at. Then I put words to the page, drew my glyphs. There. I was done.

The secret to classes like this one wasn’t to study your ass off every night. It was to have an indelible memory.

Martin, sitting to my left, was on the verge of tears and biting back the acrid flood of emotional torment about to pour forth like a reservoir behind the dam. I knew this because he wasn’t writing anything, had spent most of the past ten minutes staring at the page, looking around and glimpsing my way. I always had that nagging suspicion that his studying so hard was him trying to compensate for something. Most likely that was a very poor memory. Those two deep breaths he took just now underscored him not breathing at all the past minute. He must be one of many students now being traumatized by Orgasmic – I mean Organic. I hoped he’d do well, even though I knew that hope was in vain.

After the bell rang, I put away the novel I was reading. A few friends approached me. “That test was difficult, eh? Especially number nine. I mean, when had we ever learned something like that. How’d you think you did?”

I teleported through time, to when we were getting our graded tests back already, and I flipped to the second page where my score was written in red – way above the mean. “Yeah, I know right? No idea how to do that one.” Are you kidding me? That one was practically verbatim off the Web. “The test practically killed me.” Actually, I killed it.

I was alone with my secret, at once terrible and precious, a truth best shared with no one less they thought the lesser of me - not even him. Unlike me, everyone else was oblivious to what they were seeing, what I was doing, and it pained me that it must remain so.

As I closed my novel, click. As I got out of my seat and wrapped my jacket at my waist, click click. As I stepped to leave, click, click, click… unconsciously I took pictures of the world of dazed pre-med students about me, capturing them, scratching their heads or burying their eyes in their hands, in perfect detail on my camera. It may beget me neither photo nor film, but with it I had in a few years built up a wealth of snapshots greater than all the photos taken by the students of the university combined. Snapshots of all the websites I have ever visited, of all the pages of all the books I have ever read, of all the experiences I have ever had, all accessible with but a thought.

I waited at the entrance for him to come out. Ten minutes after I was done, his exam flew into the box with the others. Then we clasped hands as we usually do, weaving our way through the throng of faces. We shot each other grimaces of dismay, leaned on each other too. Here, my actions spoke, take solace that I am still by your side today, even as your future flees from you. He says nothing; men don’t like showing weakness, even at times like these where a good splatter of tears would work miracles, but how could I tell him that? He didn’t have to say anything; that moment I knew how many questions he had missed, and which ones. I knew this because he barely looked at me, because he walked far slower than usual, because his clammy hands felt cold to the touch, because the pulses that went quick through his hand were to the tempo of those of a man running, fleeing from pursuing nightmares, from the unfortunate truth. We went home, with only the anguished discussions of exam problems piercing the silence. The blue skies rained tears in remembrance for all those once bright-eyed pre-med students, for they had lost their way.

As for me, the flash photography never stopped.

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