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The Hodge quote board

a portrait of Hodge
photo: Williams Chemistry Dept.

J. Hodge Markgraf (1930-2007) was a chemist who talked like a down-to-earth poet. While Prof. Markgraf's gift for colorful language and unlikely analogies defies easy description, it may suffice to say that he's probably the only organic chemist to have described the Hofmann rearrangement in terms of the musical Guys and Dolls, or to have likened lithium aluminum hydride to a Gatling gun.

In the spring of 1995, Prof. Markgraf's organic chemistry students at Williams College were so taken with the way their professor expressed himself -- the way that (as one student put it) "he mixes metaphors as if they were drinks" -- that they started writing down some of his most memorable and off-the-wall comments. Among the highlights, organized by topic:

Exams & Homework

Labs & Research

Nomenclature & Structures

Reactions & Reagents

Miscellany


Exams & Homework

On how students fared on a recent test:
"Unfortunately, not all of you were above average."

On how he can't give away the answers to the final exam:
"It's not like the problem sets, where I can lead you by the hand up to the trough and put your head under the water."

On the vernal equinox:
"You should all know how to spell 'moiety.' I may put that on the final exam. See, the vernal equinox occurs, and all this learning just falls to you ... upon you ... on you."

On a student admitting an error in the correction of an exam:
"I have marked it on the final tally, but I shall not forget your Honest Abe ethical quality."

On how to attack the short-answer questions at the end of exams:
"Shoot from the hip with both guns firing."

On easy or straightforward problems:
1. "Down the middle of the fairway."
2. "A fat one right across the plate."
3. "Set up the dominoes."
4. "Crank the handle."

On nomenclature problems:
"I could fire 'em up, and you could shoot 'em out of the sky."

On designing problem sets:
"Writing these problem sets is like shooting at the moon. You don't shoot where the moon is now, you shoot where it will be three weeks from now."


Labs & Research

On how gas chromatography works:
"It's like a pig going through a python."

Upon dropping glassware:
1. "Markgraf, you hacker!"
2. "Markgraf, you buffoon!"
3. "Markgraf, you ninny!"

On progress in research:
1. "Think of it as an ascent of Everest, or that other one, where you may not get to the top, but you've established a base camp, and now you're sending out little expeditions...."
2. "Think of it as the moon-shot program, where you may not be the one who actually gets to the moon, but you were involved in one of the earlier flights. It's still important...."

On how calculations are easier than experiments:
"Paper chemistry is cheap."

On a misleading write-up of lab work:
"If you were writing a manuscript, they'd pounce all over you, and the last thing you want is to get pounced [on] by a pure and applied chemist."

Approaching the end of the semester:
"There are only three sets of prelab/postlab questions, and you're approaching sunset legislation on those."

On labs that are set up ahead of time versus labs requiring that you do everything yourself:
"It's like a Duncan Hines cake mix. You bring it home, mix it up, and by gosh you've got muffins. And they're the same muffins you got last week and the same muffins you get next week. And some people call that cooking! But scratch is always better. Scratch is always better."


Nomenclature & Structures

On the two ends of a long-chain molecule:
"...flopping around like a big sombrero..."

Trying to demonstrate an inversion of configuration by bending his fingers back:
"...And what do you get? [pause] Three broken fingers. That's what I have up my sleeve."

On tautomerism:
"You're not moving atoms, you're just sloshing electrons around in the wave tank."

On a hard-to-describe, easy-to-draw compound:
"The audio is long, the video is short."

On R and R' notation:
"We better put the prime on so you know who came to the dance with whom."

On pKa's:
1. "Unless you pull up the flap and see what I have under my sleeve, you'd think these pKa's would be identical."
2. "You should have some seat-of-your-pants ... in-your-bones feeling about pKa's. I'll put some flesh on those bones in Chapter 22."

On making complex organic molecules:
"All of a sudden, you're up to C-14, H-something, O-something, and you've got your open-toed sandals on, and you're counting fingers and toes...."


Reactions & Reagents

On the Claisen rearrangement:
"It's like those time-lapse photography fluorescences of flowers blooming. Everything unfolds at the right time."

On free-radical chain reactions:
"It's like the Rockettes' chorus line, where all the legs go up at once, or all the Fred Astaire canes come down at once."

On the rearrangement of an allyl phenyl ether with methyl groups ortho to the ether:
"It's the Patrick Ewing don't move your pivot foot rearrangment."

On reversible reactions:
"It's like Sisyphus -- the boulder rolls down on him, and you're back to starting materials."

On an irreversible reaction:
"All the sand winds up in this end of the hourglass because this reaction is irreversible."

On an ineffectual reagent:
"That molecule couldn't oxidize its way out of a paper bag."

On why five- and six-membered rings form in an enolate condensation:
"With a three-membered ring, the enthalpy is too high. With an eight-membered ring, its entropy is the problem: there's so much wig and wag that the head never meets the tail. With a five-membered ring.... It's like Goldilocks. You get too cold, too hot, and juuust right."

On the synthesis of methyl esters:
"This is dangerous stuff. It brings back memories."

On the Hofmann rearrangement, a lengthy mechanism:
"It's like that thing from Guys and Dolls: the longest-running floating craps game in New York."

On why beta-keto acids can't be isolated:
"Beta-keto acids carry the seeds of their own destruction."

On a preferred reagent:
"This gets the Consumer Reports check-rated."

On the Tollens reagent:
"It has a major limitation. It explodes. But other than that, it's a piece of cake."

On the reactivity of a substituted cyclohexane ring with a bulky axial substituent having 1,3 diaxial interactions with H atoms, versus that of the same ring with the substituent being equatorial:
"[When it's axial] it's like a fat guy in an elevator with a bunch of skinny people. The elevator stops at a floor, and all the skinny people push the fat guy out. [When it's equatorial] it's like the fat guy in an elevator by himself. The door opens, and he can get out whenever he wants to."

On ways to make acid chlorides:
"The only arrow you have in your quiver at this point is thionyl chloride."

On the SN2 reaction mechanism:
"...pushing the leaving group out of the nest..."

On how enamines are made as intermediates on the way to synthesizing something else:
"Enamines are not an end; they are only a mean."

Trying to coax out a response:
"Can you say 'dimethyl copper lithium'? Yes? You can say, and you can make, and you can use it."

On the difference between lithium aluminum hydride and LiAl(O-t-Bu)3:
"Lithium aluminum hydride is like a Gatling gun. It just keeps firing those hydrogens in there."

On how a reaction won't happen if the two reactants don't meet:
"It's like, you go to one stadium, and your friend goes to a different stadium, and there's no game."


Miscellany

Addressing a student:
"Your hair is looking neat today. It looks like your part was measured with a laser."

Welcoming a new chemistry major:
"Glad to have you drop anchor with us."

On tutorials:
"The great thing about this tutorial format is that you really have to wrestle with the material and pin it to the mat in order to learn it."

On an unsophisticated text:
"This textbook is fairly low-level pablum."

On icebergs:
"I'm like an iceberg. I have all this knowledge below the waterline, and I'm just bringing it up above decks."

On how one should learn organic chemistry by seeing common themes rather than memorizing everything:
1. "You don't want to be an interior lineman [in football], down in the trenches. You want to be up in the press box, recognizing the deep pass patterns."
2. "As opposed to French irregular verbs, which are totally memory, with organic chemistry, you can reason your way through things."

Concluding a digression:
1. "End of homily. Time for the hymns."
2. "The take-home message is, you didn't need to know any of that."

On a poorly attended lecture with many unfilled seats:
"Thanks for coming. It looks like we have a Swiss-cheese operation here."

On an incorrect response:
"No, no, no. An Ella Fitzgerald scat song has that: 'No, no, no.'"

On a nearly correct response:
"I got you where I want you, so now I'll ice it down, instead of tweaking sentences at the margins."

On the introduction of new material:
"Some of these functional groups that you haven't seen before.... We'll try to pump up your tires with those."

On how he is relating new material to previously discussed reactions:
"I'm throwing a lot of stuff at you, but I'm trying to anchor you to a lot of buoys along this waterway."

Summarizing what has just been said:
"Let's review the bidding."

Beginning a review session:
"The doctor is in. Five cents, please."

At a review session:
"A follow-up question? Presidential conferences allow that."

On the biology-chemistry basketball game:
"White profs. can't jump."

Clarifying what he means by a distance of "infinity":
"Infinity, in this case, is about six Angstroms."