PROBLEM AND PUZZLE
You have been recently hired by Jelly Belly Canada to replace the
former flavor chemist, Joe Blow. Joe was let go from the company
because he did not maintain his lab notebook properly, and seldom
documented his chemistry and formulations. You have been hired on
a trial basis and will be hired permanently only if you can help
unravel some of Joe’s flavor mysteries.
On your first day, you open the lab door, and are shocked by
all the clutter and unlabeled vials. Each vial has a unique smell. On the wall you also see a
generic and cryptic saponification procedure (see below). After countless days of gathering the
requisite spectra, you are now ready to solve the structures of the unknowns. What is a
structure consistent with the attached spectra and your assigned unknown and how would you
synthesize it???
PRESENTATION AND SUBMISSION OF DATA
Your first and last name (based on the table above) dictate your unknown number. You will be
working in a Royal Society of Chemistry (RSC) Template. Templates have specific font style for
each field. Carefully cut and paste into the document or you may inadvertently change the
fields, and hence lower your mark.
All chemical structures need to be drawn using ChemBioDraw (downloadable for free after
registering with your Ryerson email) at
https://www.cambridgesoft.com/Ensemble_for_Chemistry/ChemDraw/
DETERMINING YOUR UNKNOWN CODES
Last Name Unknown First Name Mass (g) of
Unknown
A A A ‐ E 1
B B F ‐ L 2
C‐D C M ‐ Z 3
E‐F D
G‐L E
M‐P F
Q‐S G
T‐Z I
Therefore the unknown code for Bryan Koivisto
would be
E1
Your template should incorporate only the following headings and information. Delete
any non‐essential fields (DO NOT DELETE THE MASTHEAD), and follow the template
instructions EXPLICITLY for full marks
Title – be brief, but descriptive
Author ‐ you
Address – Ryerson University, full address
Abstract – The following paper presents the structural identification of a unique and unknown
flavoring used in the preparation of X‐flavored jelly beans by the Jelly Belly Company. In addition,
this work also proposes a synthetic scheme for the synthesis of the flavoring.
Introduction
‐ to be done last
‐ no more than 250 words, provide some background information about your unknown molecule
once you know what it is. (I would like to learn something too, and I do not want a rehash of
Wikipedia – Scifinder would be best)
‐ show a ChemBioDraw picture of your unknown and call this Figure 1.
‐ In one sentence state the object of vLab 1.
Synthesis
‐ starting from any hydrocarbon (and using the reactions previously taught in CHY142) present a
reasonable synthetic scheme (Scheme 1) for the synthesis of your unknown flavor. Be sure to
use ACS document style with your ChemDraw
‐ accompany your figure, by writing a 100‐150 word paragraph describing your reaction
sequence, and why you chose this route.
Results and Discussion
‐ Using Chemdraw, simulate your 1H‐NMR spectrum, and include this as Figure 2,
‐ In less than 100 words explain why this NMR is consistent with your unknown molecule
Summary and Conclusions
‐ Two sentences about the successful characterization and synthesis of your molecule
Experimental
‐ Using the mass provided for your unknown, calculate the highlighted quantities and rewrite the
procedure below for your unknown.
Saponification of unknown: In a 100 mL single neck RBF, water (50 mL), the unknown (x g, y
mmol) and a stoichiometric amount of potassium hydroxide (x g, y mmol) were combined. The
reaction was refluxed for 2 hours, and cooled to room temperature. The water mixture was then
extracted with diethyl ether (2 x 25 mL). The ether was discarded, and then the water layer was
acidified using excess concentrated HCl (5 mL). The water layer was then extracted a second time
with diethyl ether (2 x 25 mL), and the ether extracts dried over using magnesium sulfate.
Removal of the volatile solvent, yielded the desired product (x g, 75.9%)
References
‐ At least two references (most likely from your introduction) are to be included in ACS format.
OTHER THINGS
1. Your total submission should not exceed two pages, but should be longer than 1 page
2. All chemdraws should be 80% of their original ACS style chemdraw size.
Spectra for ALL unknowns are on the following pages
UNKNOWN A
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C6H12O2
1H‐NMR
13C‐NMR
UNKNOWN B
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C7H14O2
1H‐NMR
OTHER INFORMATION
13C‐NMR
UNKNOWN C
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C7H14O2
1H‐NMR
13C‐NMR
UNKNOWN D
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C9H10O2
1H‐NMR
13C‐NMR
UNKNOWN E
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1715 cm‐1, 2800 cm‐1
Chemical Formula from HR‐MS: C5H10O2
1H‐NMR
13C‐NMR
UNKNOWN F
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C9H10O2
1H‐NMR
13C‐NMR
UNKNOWN G
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C7H14O2
1H‐NMR
13C‐NMR
UNKNOWN H
Mass of sample:
Code on vial:
Diagnostic IR Peak Listing: 1725 cm‐1
Chemical Formula from HR‐MS: C9H10O2
1H‐NMR
13C‐NMR
