Chemistry Everday for Everyone

Sherlock Holmes and the Nebulous Nitro

Thomas G. Waddell and Thomas R. Rybolt
Department of Chemistry, University of Tennessee at Chattanooga, Chattanooga, TN 37403

The following story describes a chemical mystery “Lestrade,” Holmes said, “If you don’t mind, please
with an emphasis on knowledge in basic organic chem- run through the particulars of the case once more, for
istry, scientific observation, and reasoning skills. This is Watson’s benefit. In fact, I myself should like to review
the eighth article in a series presenting a scientific prob- the salient events.”
lem in mystery form in the context of the popular and “Gladly, Mr. Holmes,” replied the Inspector.
beloved characters Sherlock Holmes and Dr. Watson (1– “Grounder was stabbed, Dr. Watson, in the back of the
7). There is a break in the story where the reader (stu- neck as he sat at his desk at the university. His back
dents and teachers) can ponder and solve the mystery. was toward the door and the door was unlocked but usu-
Sherlock Holmes provides his solution in the paragraphs ally kept closed. So, anyone could have done it easily
following this break. enough. We briefly considered that he was murdered by
a colleague or administrator in retribution over that
The Story fraudulent research scandal. But that case is years old
Autumn in London had become my favorite time of now and Grounder had worked in humiliation and iso-
the year. On this particular afternoon, one that would lation for so long.
end with tragic news, I had been returning from a medi- “And, moreover, here’s the kicker. We have many wit-
cal case on Vauxhall Bridge Road. Under the bluest of nesses from his Organic Chemistry class who testify that
skies, I walked the last few blocks toward 221B Baker after the last quiz he publicly and angrily accused one
Street through crisp golden leaves. The subject of mur- of the students of cheating…looking at another’s paper.
der was furthest from my mind. As I entered our flat, He told the class that, later in the day, he would report
ready to engage Sherlock Holmes in a vigorous discus- that person to university authorities for instant expul-
sion of the qualities of the season, I was met instead with sion. Professor Grounder was murdered in his office be-
the sound of Holmes’ voice and the sight of Inspector fore any such report was filed.”
Lestrade reclined in my own chair before a crackling fire. Holmes’ chin rested on his chest and he made no
Holmes held some manuscript rolled in his fist and response as Lestrade continued.
tapped the chair with it as he spoke. “One more thing, Mr. Holmes. Dr. Grounder’s adjoin-
“C. Loring Jackson is a Harvard graduate, Inspec- ing laboratory was vandalized at the time of the mur-
tor. He studied with Bunsen at Heidelberg and with der. There was much broken equipment, and his valu-
Hofmann at Berlin. I have read that he has carried out able research samples of natural products were smeared
significant studies with substituted aromatic halogen on the walls, as if in a violent fit of anger.”
compounds in which the halogens were readily replace- “Who was the accused student?” I inquired.
able by negative ions owing to strongly electron attract- “We have no way of knowing, Dr. Watson, since he
ing groups.” did not reveal the name to his class or to anyone else.
“I am very sorry to have asked, Mr. Holmes,” re- Of course, if we could identify that student, we would
turned the sallow Lestrade, shaking his head in bewil- have ourselves a prime suspect with opportunity and mo-
derment. “But surely that information is not relevant to tive.”
the present situation.” Holmes, now tapping his cheek with the collection
“Perhaps not, Inspector,” Holmes replied, “but… Ah! of rolled papers, remarked in a casual manner, “If luck
Here is the faithful Watson! is with us, there may be a way to discover the dishonest
“Watson, join us here by the fire. I trust that you do student, Lestrade.”
not mind if Lestrade occupies your chair for the time “How can that be, Mr. Holmes?” Lestrade questioned.
being?” The rat-faced policeman looked up at me and Holmes unrolled the manuscript and flattened the
blinked one eye feverishly. stack of papers on his lap. “Watson, these are the stu-
“I do not mind,” I replied coldly. dent quizzes from Dr. Grounder’s Organic Chemistry
Holmes’ tone suddenly became grim. “Watson,” he class. The inspector was thoughtful enough to bring them
said, “Dr. Floyd Grounder has been murdered.” along this afternoon. They might prove informative.”
“Murdered? Grounder? That chemistry professor? Lestrade rocked forward in my chair. “They might,
Holmes, who would ever want to murder a chemistry sir. But I don’t see how. There are 25 students in the class
professor?” and there are 25 quiz papers. As I see it, there are, there-
“Hah!” ejaculated Lestrade. I had momentarily for- fore, 25 suspects. A bit of a challenge even for you, Mr.
gotten that he was present. Holmes!”
As my initial recoil faded, I soon remembered the “We shall see, Inspector, we shall see. Now, if you
dishonored Professor Floyd Grounder. A few years ago, will excuse Watson and me, we will look into this little
he had emerged as the guilty party in the unfortunate problem with pleasure. Perhaps in a day or two I shall
Fraudulent Ketone case (2) in which Holmes, by identi- ring you up at the Yard.” Lestrade stood up, and with a
fying the dishonest researcher, spared the reputations nod in my direction and with his coat under his arm, he
of Grounder’s innocent colleagues, the Chair of Natural departed, closing the door behind him none too softly it
Science, and one of the world’s greatest universities. Now seemed to me.
Grounder had been murdered and Sherlock Holmes was “Now, Watson,” Holmes said, rubbing his hands to-
once again in consultation with Scotland Yard, as he had gether. “Let us have a look at these quizzes.” He handed
been so many times in our years together. me the top paper and I read the single question:

Vol. 73 No. 12 December 1996 • Journal of Chemical Education 1157

Chemistry Everyday for Everyone

Write a balanced chemical equation illustrating one and I could not help but notice the familiar smile on his
of the numerous aromatic substitution reactions re- face and the gleam in his eye.
cently studied by C. L. Jackson. “Mrs. Hudson will contact the street urchin Wiggins
of our troop of Baker Street Irregulars, and he will in
“C. L. Jackson, Holmes? That name is familiar to me.” turn track down Effie Gaboriau and John Mincing at the
“Indeed it should be, Watson. I was telling Lestrade University. That should not be too difficult and I predict
about him when you came in. I had a brief look at the that at 9:00 tomorrow morning we shall be chatting with
papers before you arrived and Lestrade was asking about these two students before this very hearth.”
him then. Actually, I met C. L. Jackson on the Continent We had our supper early and for the remainder of
some years ago and had the opportunity to be of service the evening Holmes happily worked in his laboratory
to him in a professional manner…before your time, corner, pursuing his current researches into the identi-
Watson. But for now, my friend, with the accompaniment fication of animal saliva, while I labored diligently
of my favorite briar, I shall attempt to track down a mur- through a long and depressing Russian novel.
derer amongst all these formulae and equations.” At the appointed time the next morning, Mrs.
During the next hour, the air of our flat became Hudson knocked and escorted into our lodgings the two
dense with the fumes from Holmes’ acrid pipe, as he re- students from Dr. Grounder’s organic chemistry class
peatedly studied a page then flipped furiously through who had attracted the attention and scrutiny of Sherlock
the student papers. I occupied myself well enough with Holmes. Effie Gaboriau was clothed in an attire of car-
the Times, knowing that with patience (and luck, as nival quality, smelling (albeit faintly) of a strange per-
Holmes had said), any clues present in the examinations fume, undoubtedly inexpensive. She was a girl of small
would be revealed. stature, with long black hair and short blunted fingers.
“Look at this, Watson,” Holmes remarked suddenly. He Her face projected a foul mood. Holmes, in an uncharac-
had removed two pages and smoothed them out on the cof- teristic manner, stooped to kiss her hand, affecting a brief
fee table between us. It is necessary at this point to repro- bow in the process. Effie’s companion, John Mincing, a
duce exactly the quiz papers which I saw before me: dashing young man, dressed smartly in the latest fash-
ion, took the chair offered by Holmes and introduced
himself with an air of confidence.
“We are at a loss as to why we are here, Mr. Holmes.
But, of course, quite curious. Can you enlighten us?”
“I frankly do not have time for this,” added Miss
Gaboriau in an irate tone that matched her expression.
“My class work takes all my time. What is the meaning
of this summons?”
Holmes replied in his most gracious manner. “Be-
lieve me, Miss Gaboriau, when I tell you that your visit
is a matter of great importance. Dr. Watson and I thank
you for your cooperation in coming to see us and we as-
sure you that it will take very little time. I have only
one question to ask each of you and then you may in-
stantly return to your University.”
“Proceed, Mr. Holmes,” replied Mincing.
“Miss Gaboriau,” asked Holmes, “What is the sym-
bol for the element sodium?”
“What!” cried Effie. “You bring me here to ask chem-
istry questions!”
“Answer, please,” Holmes replied courteously.
“N.....a,” she said, spelling the elemental symbol.
Holmes turned to Mincing. “Mr. Mincing, what is a
substitution reaction?”
“Well, I’ve had some difficulties with that concept,
Mr. Holmes. But generally I think that in those cases
some negative unit displaces a Cl on some carbon
atom.”
Holmes stood up immediately. “Thank you again for
coming, Miss Gaboriau, Mr. Mincing. I pray that your
future at the University will be most successful.” The
students, without disguising their astonishment, left
221B without a word. I closed the door after them and
returned to Holmes’ side.
“Holmes, are you mad? I thought that you were in-
vestigating a case of cheating and homicide!”
“My good fellow!” he countered. “Lestrade will be
delighted that we have cleared this up. Perhaps some
promotion in rank will be his reward for our persever-
ance in this matter.
As I looked down upon them without a glimmer of un-
derstanding, Holmes rang for Mrs. Hudson. Upon her Stop Here and Solve the Mystery
arrival at our door he whispered a message in her ear

1158 Journal of Chemical Education • Vol. 73 No. 12 December 1996

 Chemistry Everday for Everyone

“Indeed I can, Watson,” Holmes cried. “Did you ob-

Holmes and Lestrade are correct in their as- serve that Effie knew the symbol for sodium?”
sumption that the cheater and the murderer are the “Yes,” I replied tentatively.
same person. This mystery can be solved with sound “Then, in the first line of her answer, why did she
reasoning and with the application of correct organic foolishly write N2+ instead of Na+?”
chemistry principles. Some knowledge of the previ- I looked at the papers again, carefully focusing my
ous Fraudulent Ketone case could be helpful but is attention, and finally saw it. “ From a distance she
not essential. thought that Mincing’s ‘a’ was a ‘2’.”
1. Why was the attention of Sherlock Holmes drawn Holmes answered in a quiet voice. “Excellent,
to the quiz papers of those two students? Watson, excellent,” and with his kind words the warm-
2. What did Holmes learn from examining their an- est feeling I can remember washed my soul.
swers? Holmes rose from his chair and went to the mantle
3. Who cheated on the quiz and murdered Professor above the fireplace for a plug of shag tobacco. “There is
Grounder? a bit more, Watson. Mincing had difficulty with the con-
The following paragraphs contain Holmes’ cept of a substitution reaction, but answered my ques-
chemical solution to this mystery. Compare your so- tion to him in an awkward but correct manner. His quiz
lution with his. answer is consistent. What he crossed out of his product
structure is a Cl, which he did at the end when he real-
ized that the negative unit must displace the Cl. Effie
The Solution had undoubtedly copied the Cl, then later, failing to re-
alize that Mincing had crossed it out, left it in place. Her
“I am sorry, Holmes. It certainly would be less frus- answer makes no sense at all for a substitution reac-
trating to me if I could follow your reasoning on some tion.”
occasion.” “Holmes, could not these symbols tell a different
“My good fellow,” said Holmes with an affectionate story. Might we not interpret the quiz papers in a differ-
smile. “You have always been my Boswell and shall re- ent way?”
main so. You have seen these two student quizzes. What “No, Watson, the tale is clear. But…”—he smiled
remains to be clarified?” playfully at this point—“did you notice how smartly I
“Well, first of all,” I suggested in an injured tone, kissed Effie’s hand upon her introduction? Yes? Well,
“how did you select Miss Gaboriau and Mr. Mincing from Watson, I was only confirming the faint odor of a ter-
twenty-five papers?” pene on her presence. Grounder’s precious research
“Excellent question!” roared Holmes with what I chemicals from the soapwort spider-flower, remaining
thought was undue enthusiasm. “Watson, the quiz ques- after her violent outburst of murder and vandalism. Ter-
tion clearly implies that there were numerous examples penes, Watson, like the oil of lemon, often have intense
from which to select an answer. Now, Miss Gaboriau and and characteristic aromas. Remember the Fraudulent
Mr. Mincing selected the same equation to present. This Ketone case, my good fellow!”
in itself is not suspicious, but coupled to the fact that So I knew then what had happened. “Effie
identical (and rather foolish) mistakes were made by Gaboriau, Holmes, a cheat and a murderer. She would
both students leads me to the inescapable conclusion that have had no trouble stabbing the professor, with no wit-
one student, our murderer, copied from the other, a pre- nesses. Do you still insist upon giving Lestrade credit
sumed innocent.” for your successful resolution of his case?”
“What foolish mistakes are you referring to, Holmes was solemn. “Oh yes, Watson. There is a pas-
Holmes?” I asked, as I held the two test papers closer to sage, older than England, from the Tao Te Ching by Lao
the light of our gas lamp. Tzu, which I like to remember.”
“First of all, Watson, a nitro unit is not –NO3 but The secret waits for the insight
–NO2. This mistake appears in no other paper in the Of eyes unclouded by longing.
class. Secondly, in a reactant line, the (COOCH)2 should Those who are bound by desire
be (COOCH 3)2 as was written correctly in the product See only the outward container.
line. This mistake appears in no other paper, only these
two. Moreover, both students placed the respective for- Literature Cited
mulae at the same positions on the page. Neither do I
find this feature in any other paper. There had to have 1. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1989, 66, 981–982.
been collaboration on this answer.” 2. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1990, 67, 1006–1008.
3. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1991, 68, 1023–1024.
“I see that now, Holmes. Indeed, it is sound reason- 4. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1992, 69, 999–1001.
ing. But you cannot tell who copied the answer from 5. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1993, 70, 1003–1005.
6. Waddell, T. G.; Rybolt, T. R. J. Chem. Educ. 1994, 71, 1049–1051
whom!” 7. Rybolt, T. R.; Waddell, T. G. J. Chem. Educ. 1995, 72, 1090–1092.

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