Stereoselective reduction of camphor lab report

Loperamide is a peripherally selective opioid available without a prescription used to suppress diarrhea. You will need a special microscale kit, which you will obtain from your TA at the beginning of the lab period and return at the end.

Ege, Chapter 10,12,13; Microscale Techniques In this experiment you will convert a chiral alcohol into its chiral diastereomer using a scheme involving oxidation to the ketone followed by stereoselective reduction to the diastereomer using sodium borohydride: The iodine then reacts with the starch in the test paper to produce the characteristic purple colour of the starch-iodine complex.

All the steps are irreversible. Sodium borohydride was slowly added in portions and the mixture was heated. While the basic principles and operations are the same as those in the macroscale experiments that have been used so far in the course, the techniques and equipment employed for sample manipulation, reactions, extractions, distillation, recrystallization, etc.

Alan Shusterman, Reed College. IR spectroscopy is particularly useful in determining the functional groups in a compound, and thus, is incredibly helpful in determining whether the reduction product formed.

The bottom-ide attack pushes the alcohol OH group into an energetically unfavorable axial position. Overall, this reduction reaction of camphor into isoborneol was completed relatively successfully. Newman projections for the cis sodium borohydride reduction product.

Dissolve this solid in methylene chloride then add anhydrous sodium sulfate to remove any water in solution. After extensive analysis of 1H-NMR spectra, IR spectra, and melting point measurements, it is clear that sodium borohydride favored the trans product over cis product in a ratio 2.

This carbonyl group is the main difference between the lab data and literature data but this only means that the reaction did not go to completion but the reaction still proceeded. Therefore, this demonstrates that the product has a hydroxyl component as in isoborneol and borneol.

The IR spectrum of the starting material contains a characteristic peak at Conclusion The purpose of this experiment was to investigate the stereoselectivity of various hydride reducing agents. This forms the thermodynamically favored product. Looking down carbon two-carbon one left and carbon one-carbon six right.

L-Selectride is a bulky, sterically hindered reducing agent, and thus, does not have the ability to attack from the top face of the starting material.

Reduction of Camphor

By dividing the integration for the trans peak by the integration for the cis peak, the relative ratio of trans to cis product was determined to be 2. The IR spectrum of the hydride reduction product exhibits a broad peak at The ethyl acetoacetate contains both a ketone and an ester functional group.

Dissolve this solid in methylene chloride then add anhydrous sodium sulfate to remove any water in solution. All the steps are irreversible. In many cases opioids are a successful long-term care strategy for those with chronic cancer pain.

Hence, it can only be used in anhydrous, nonhydroxylic solvents like THF or diethyl ether.Place 2 mL of methanol in a 10 mL rb flask, and add g of camphor. Swirl until the camphor dissolves, and then add g of sodium borohydride. CAUTION. Do not add the borohydride all at once; divide it into four or five portions and add over a period of about five minutes, with swirling.

if the reduction was stereospecific by measuring the optical rotation of the starting material and product(s).

If the reduction was stereospecific, optically pure (+) or (-) camphor should form only (+) or (-) borneol, or only (+) or (-) isoborneol, with no loss of optical purity.

Hydride Reduction Reactions: A Stereoselective Adventure

In this experiment, you will start with either (+) or (-) camphor. Here is the best resource for homework help with CHEMISTRY Orgo 1 at University Of Massachusetts, Boston. Find CHEMISTRY study guides, notes, and stereoselective reduction of camphor 3 pages.

TLC lab Iodination of Salicylamide Lab Report 3 pages. lab report 3 chem doc. The starting material, camphor, has been used for centuries in religious ceremonies as a symbol of consciousness and in traditional Chinese medicine to help reduce pain.1 Research has focused on 5/5(2).

Mar 29,  · Camphor is a pleasant smelling bicyclic ketone that can be reduced by a hydride reducing agent.

Reduction of Camphor

The carbonyl carbon is a prochiral center in that reduction to the alcohol will create a chiral center on that Resolved. Results and Discussion: Based off of the data, both isoborneol and borneol were synthesized from the reduction of camphor as seen in the gas chromatography data so the experiment was successful.

The camphor had an incense-like smell and the isoborneol–borneol mixture had a similar odor.

Stereoselective reduction of camphor lab report
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