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Experiment 6

Experiment 6

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Published by Bartholomew Szold

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Published by: Bartholomew Szold on Oct 09, 2012
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CHEM 2311L/2411LLab Report Cover SheetName: _________________________TA: Doug Jackson/ Matt McKinley/ Tom IrvinDate: _________________________Experiment: _____________________________________________________Pre-lab
(25 points)Title ____________ (2 points)Introduction ____________ (13 points)Table of Reagents ____________ (5 points)Safety Information ____________ (5 points)
(20 points)Procedure/Data/Obs. ____________ (5 points)Data Sheet ____________ (5 points)Quality Data/Spectra ____________ (10 points)Recorded
(50 points)Results/Spectra, Discussion ____________ (35 points)and ConclusionsCalculations ____________ (10 points)Answers to Questions ____________ (5 points)
Discretionary Points
(5 points) ____________` (5 points)
____________ (100 points)
TA Comments:
Dehydration of Alcohols
One important way to form alkenes in organic synthesis is by dehydration of analcohol precursor. The dehydration reaction proceeds under thermal conditions inrefluxing acid through a carbocation intermediate.The thermal conditions for this reaction are high temperature and a long reactiontime. Under these conditions, if multiple products are possible, then the more stableproduct should be the major product and predominate. The more stable product is known
as the “Zaitsev Product.”
It is not known to what degree the Zaitsev Product will predominate in thereaction. In other words, it is not able to predict what the product percentage will be inthe final product of a reaction.The goal of this experiment is to dehydrate 3-methyl-3-pentanol to form alkeneproducts in some unknown ratio. Proton nuclear magnetic resonance spectroscopy willbe used to determine the ratio by looking at the relative proton integration. Using the
integrated spectra of the product mixture, the product distribution (% of each product)will be determined for the final sample.NMR instruments rely on large magnetic fields to align nuclear spins in a way tomake them detectable to a probe. Every proton of a compound in a different chemicalenvironment gives a different H NMR signal because every position in a compoundexperiences a shielding effect due to its electron cloud. The chemical shift of thespectrum is affected by several things, the close a proton is to an electron withdrawingatom, the greater the shift, the proximity to a double bond or aromatic ring.
Table of Reagents
 Name Structure MolecularWeightBoilingPointMeltingPoint3-methyl-3-pentanol102.174 g/mol 122.4 °C -23.6 °CPhosphoric Acid 98 g/mol 158 °C 42.35 °C
Always lab goggles during the experiment. Remember to never heat a sealedapparatus. Phosphoric acid is corrosive, so in addition to goggles, gloves are required.The starting material and products of the experiment are flammable so avoid any sourcesof ignition.

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