Organic Chemistry Lab (CHE 276)
Final Exam Information & Study Guide
Fall 2011
Fi nal E xa m:
Dat e:
Friday, December 16, 2011
Tim e:
10:15 am -12:15 pm
Ro o m:
last name begins with A – K:
Grant Auditorium (Law)
last name begins with L - Z :
Gifford Auditorium (HBC)
Office H o ur s for Fi nal Ex a m We e k:
Prof Totah and TAs will hold office hours as usual through 5:00 pm on Thursday, 12/15.
R ule s for the Ex a m:
1. Students must take the exam in the room to which they are assigned (above).
2. Backpacks, coats, hats, etc. must be brought to the front of the room.
3. Please sit every other seat.
4. All hats must be removed.
5. No cell phones, calculators, blackberries, iPODs, etc. are allowed. These items must be turned off and
put away if you bring them to the exam room.
6. Once the exam begins you may not leave until you finish & hand in your exam. Please plan accordingly!
7. You are required to do your own work. You may not consult with others, use any notes, or outside
materials during the exam.
8. Cheating in any form will not be tolerated. If you cheat on the final you will receive an F in the course. A
letter reporting the incident will also be submitted to the Dean in accordance with the academic integrity
policies of Syracuse University.
9. The final exam will not be returned. You may use pencil or blue/black ink when completing the exam. Do
not use red.
10. You must show a photo id when you turn in your exam.
11. Failure to comply with the rules of the exam may result in your expulsion from the exam room.
Organic Chemistry Lab (CHE 276)
Final Exam Information & Study Guide
Fall 2011
A bo ut t he Fi nal :
The final exam is comprehensive and will cover material encountered in experiments 1 - 9. This is a closed
book, written exam. The format is short answer. Below is a general overview of the important topics we
have covered in each experiment. This overview is by no means exhaustive, but may help you to identify
areas of study. This final exam will test your ability to interpret experimental data, and your understanding
of general concepts & the theory behind the techniques we have learned over the course of the semester.
You may be asked to execute simple calculations of the type we have encountered this semester. No
calculators will be required (nor are they allowed). You should also have a general understanding of the
reactions we ran this semester. Be sure to look over the questions that accompanied each lab report.
Answers are posted on the course web site.
Some topics that stand out when looking over the material include the following:
Ex p 1: T hi n La ye r Ch r om at o gr ap hy
basic technique of TLC  dos and don'ts
relationship between the stationary & the mobile phase
factors that influence separation & rate of elution
substrate interactions with the mobile phase
solvent polarity
visualization of TLC plates
Rf values
definition
effect of TLC plate length, solvent polarity, compound functionality
calculation
utility of TLC
Ex p 2: R ec ry stal liz ati o n & M elti n g P oi nt
basic technique of recrystallization  dos and don'ts
use in the purification of solids
good vs. bad recrystallization solvents
collecting crystals
% recovery calculation
basic technique of melting point  dos and don'ts
use of melting point to identify compounds
melting point as an indicator of purity
factors than influence melting point
Ex p 3: D ist ill ati on
basic technique of distillation  dos and don'ts
simple vs. fractional distillation
utility
apparatus
temperature vs. time behavior
phase diagrams
theory of separation
(over →)
Ex p 4: E xtr acti o n
basic technique of extraction  dos and don'ts
distribution coefficient
separation of mixtures
protocols for separating weak/strong organic acids, organic bases, neutral compounds
reactions that allow separation
identifying organic vs. aqueous layers
use of IR to distinguish carboxylic acids & phenols
Ex p 5: C ol um n Ch r om at ogr ap hy
basic technique of column chromatography  dos and don'ts
background & theory
basis for separation
order of elution
relationship to TLC
use of IR to identify ketones
Ex p 6: D e hyd r atio n & G a s Ch r om at ogr ap hy
dehydration of alcohols
reaction & mechanism
yield calculations
identification of limiting reagent
theoretical yield
percent yield
gas chromatography
basis for separation
interpreting the chromatograph (including relevant calculations)
retention time
determining component ratios
use of IR to distinguish alcohols & alkenes
Ex p 7: S ynt hes is o f a n Al ky n e fr o m a n Al ke ne
bromination & dehydrobromination reactions
yield calculations
as above (exp 6)
overall yield
use of TLC to evaluate reaction success
Ex p 8: Nucle o ph ilic Su bstit uti o n
predict SN1 vs SN 2 reactivity based on structure, leaving group, reaction temperature; solvent polarity
with NaI in acetone
with AgNO3 in ethanol
side reactions
Ex p 9: Is olat io n & Ide nti fic ati o n o f a n U n kn o wn
review techniques (as above)
use of IR to distinguish carboxylic acids & phenols
use of IR, mp and tlc to identify an unknown