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site map read first about course lab manual appendix

Lab I

Lab II


Lab IV

Lab V

Lab VI



Lab IX

Lab X

Lab XI


Lab XI: Designer Experiment--Part Deux! or reDUX?!
Pre-lab Work

After consulting with your instructor about the success of your original Designer lab and any possible changes and/or improvements that can be done to it, please submit your New and Improved Designer Lab Plan Worksheet no later than NOON on Friday, July 5th. Please include your original Designer Lab Plan Worksheet and TPC to the new and improved Designer Lab-Part Deux Worksheet with the new TPC as well.

Similar to your original Designer Lab worksheet, your new and improved plan should include:

  • the overall reaction that you will be doing
  • the purpose or reason for the experiment and/or the chemistry question you want to answer and how it differs from your original Designer Lab
  • a list of the possible products
  • how you will analyze your products
  • a TPC which includes the amounts of reagents you will be using, all of your expected products, and their theoretical yields.
  • What changes were made to your original Designer Lab.

Pre-lab Questions:
(Please turn in the answers to these questions when you arrive to lab.)

1. Please state your new purpose and hypothesis for your new and improved Designer Lab.
2. If your experiment goes as planned, what are the products that you hope to produce? What are the most likely masses (i.e.-M+ and likely large fragments) that you expect to see in your product's MS data?

This lab is intended to be A SECOND CHANCE!

Following the scientific method, we always hope to improve upon the results of a past experiment or design an experiment that elaborates on what our first experiment has already shown us. Rarely do you get the chance to improve or investigate any lab reaction further, yet this lab will give you just that chance.

Again, modeling your new and improved experiment after the Competing Nucleophiles lab and with consultation with your instructor, each student will be doing her own individual experiment to try and answer her original question about nucleophilic substitution or elimination reactions OR a slightly different, but related question to their original Designer Lab.

Please make sure to meet with your instructor to ensure that your new experimental procedure is an improvement over your original Designer Lab procedure.

Experimental Work


  • To obtain new information from your new and improved designer experiment.
  • To see if your new or modified hypothesis, or your predicted outcome of the experiment, is correct.
  • To answer your chemistry question.

Experimental Procedure

Since each student will be performing her own experiment, there are no specific laboratory instructions. Things to keep in mind are:

If you have any trouble identifying any of your products,
please see your instructor immediately!
[You need time to generate your oral presentation and you can’t do that until you know what you made in both your Designer labs.]

Post-lab Questions...Oral Presentation during our last lab!

Plan to speak for about 5-10 minutes/person.  Your presentation should be sufficiently interesting to retain the attention of the other students!  You may use overhead transparencies, PowerPoint, other visual aids and even your audience...Be kind!  :)  
Be creative…and funny noises during your PowerPoint presentation do not count as ‘creative!’

The presentation should include information from BOTH Designer Labs:
An Introduction which includes:
--The chemical reaction(s) you attempted to do in lab and the type of mechanism you thought your reaction(s) would go through, i.e.-Sn1, Sn2, E1 or E2.
--Why you chose your reaction(s).
--What question you were trying to answer with your reaction(s) (Purpose).
--What answer you thought you would get with your reaction(s) (Hypothesis).
--Any unusual procedural step(s) that were performed in your lab (i.e.-any significant procedural step that was NOT in the Competing Nucleophile lab procedure.
A Results section which includes:
--A labeled GC of your reactants and a labeled GC of your products from each lab.  [Please label each peak with the structure of the compound responsible for the GC peak.  (Please bring your MS analysis, BUT…do NOT show us your wonderful analysis of your MS data for each GC peak…unless you are asked for it by one of your audience members.  Otherwise, we’ll take your word for your identification of the compounds in your GC!)
--Any other data that helps support what took place in your reaction(s), i.e.-FTIR data of organic starting materials versus organic product.
A Conclusion section which includes:
--A review of your original hypothesis and 'new and improved' hypothesis
--An explanation of the chemistry that actually took place in both your experiments.

Lastly, as in lecture, class participation matters.  Everyone must ask at least one question to a presenter throughout our lab. If you think your instructor didn't hear your question...ask more than ONE! :)

Your 'Designer Lab Conclusion' will be your presentation materials (i.e.-overheads, PowerPoint slides, puppets, etc...) which contain your complete analysis and conclusions of both your Designer labs.  Please email them to your instructor. 


Here are the chemicals that are available for your Designer Experiment:

Alcohols: 1-heptanol, 2-heptanol, cyclohexanol, 2-methyl-2-hexanol, 1-nonanol, 2-nonanol, 1-methylcyclohexanol, 2-methylcyclohexanol, benzyl alcohol, phenethyl alcohol, sec- phenethyl alcohol, 2,4-dimethyl-3-pentanol, 3-hexanol, 3,3-dimethyl-2-butanol, trans-2-hexen-1-ol

Alkyl Halides: bromocyclopentane, chlorocyclopentane, bromocyclohexane, chlorocyclohexane, iodocyclohexane, 1-chloroheptane, 1-bromoheptane, 1-iodoheptane, 2-bromoheptane, bromomethylcyclohexane, 1-bromo-2-ethylhexane

Acids and Bases: 18M sulfuric acid, 12M hydrochloric acid, 15M phosphoric acid, glacial (100%) acetic acid, 12M potassium hydroxide, saturated sodium bicarbonate

Salts and Drying Agents: ammonium chloride, ammonium bromide, ammonium iodide (Do not mix this with sulfuric acid!), potassium acetate, sodium bromide, sodium chloride, sodium iodide (Don't mix with sulfuric acid!), anhydrous magnesium sulfate, silver nitrate in ethanol, sodium ethoxide in ethanol

Solvents: dimethylformide [DMF] (a polar organic aprotic solvent), tetrahydrofuran [THF] (another polar organic aprotic solvent), water, acetone, hexanes, methylene chloride, diethyl ether, ethanol, methanol

**NOTE: Do not mix ammonium iodide or sodium iodide with sulfuric acid!!!**

**If you wish to order a chemical NOT on the list of chemicals above,
please contact your instructor immediately!**

Designer Lab Proposal Form--Part Deux:

Please model your procedure after the Competing Nucleophiles Lab. This must be a synthetic reaction!! Do not do a test tube lab as was done in the Alkyl Halide lab!!


Lab day:

Question to be answered and how it differs from original question:




Equation for expected reaction (use ChemDraw to write your reaction):


Predicted Major product (Show ChemDraw structure):


Predicted Minor product(s) (Show ChemDraw structures):


Do you expect the reaction to go SN1__ SN2___ Elimination___ Other___ (explain):


Instruments to be used to analyze my product:


Please include a completed TPC
with the appropriate amounts of each reactant, their chemical properties, and theoretical yield, if applicable.

(Use similar molar quantities as in the
Competing Nucleophiles or the Dehydration Labs.)