The Hodge quote board
photo: Williams Chemistry Dept.
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
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
"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
"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
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
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
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
"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."
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
"...And what do you get? [pause] Three broken fingers. That's what I have
up my sleeve."
"You're not moving atoms, you're just sloshing electrons around in the
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
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
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
On an irreversible reaction:
"All the sand winds up in this end of the hourglass because this reaction
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
"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
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
On the reactivity of a substituted cyclohexane ring with a bulky
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
On ways to make acid chlorides:
"The only arrow you have in your quiver at this point is thionyl
On the SN2 reaction mechanism:
"...pushing the leaving group out of the nest..."
On how enamines are made as intermediates on the way to
"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
"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
"It's like, you go to one stadium, and your friend goes to a different
stadium, and there's no game."
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."
"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
On an unsophisticated text:
"This textbook is fairly low-level pablum."
"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
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
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
"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."