01:504GFile Details4CH003/UM1: Fundamentals of...IntroductionNaBH4OHC=0HbenzophenonediphenylmethanolKetones are readily reduced to secondary alcohols by reaction with sodiumborohydride. The aim of this experiment is to determine the time required toeffectthe complete conversionof the ketone, benzophenone todiphenylmethanol at room temperature. This investigation may be achievedby isolating and analyzing the reaction product after different reduction times.Infrared spectroscopy affords a convenient method of analysis; by comparingthe IR spectrum of the crude reaction product at different time intervals onewould expect to see the intensity of the hydroxyl absorption peak increaserelative to that of the original carbonyl peak. From this you can deduce theoptimum time for the reduction process at room temperature.ProcedureNote the "reduction time" that the demonstrator assigns to your group.Different groups will be assigned different times, eithert = 2.5 minutes, 10minutes or 30 minutes.Add benzophenone (1g, 0.005mol) and ethanol (10ml) into a 250ml conicalflask and swirl until it dissolves.In a separate small beaker make a solution of sodium borohydride (250mg) inwater (2ml).dissolution if required.You may carefully warm this under a warm tap to helpPrepare a mixture of iced water (80ml) containing 2M hydrochloric acid (20ml)in a 250ml beaker and store it on an ice bath.Test that your stopwatch works and when ready add the sodium borohydridesolution in one go to the benzophenone solution in the conical flask.Immediately start timing and when you get to your assigned time (x minutes)quench the reaction by precipitating out the crude reaction product by additionof the cold acidified water mixture. Transfer the contents of the conical flaskto a 250ml separating funnel and wash with an aliquot of diethyl ether (50ml).Run off the aqueous layer into a clean beaker, and collect the organic etherlayer in a conical flask. Replace the aqueousyer into the sefunnel3and re-extract with a second fresh aliquot of diethylether (50ml). Discard thespent aqueous layer and combine the ether layer in the separating funnel.Wash the ether layer with a fresh aliquot of distilled water (50ml), remove thewashing and transfer the organic layer into a clean 250ml conical flask. Drythe organic layer over anhydrous magnesium or sodium sulphate. Filter offthe drying agent through a fluted filter paper and collect the filtrate directly in around bottomed flask (placed on a cork ring).1 PreviousNext3000DashboardCalendarТо-doNotificationsInboxLO 01:504GFile Details4CH003/UM1: Fundamentals of...ne penzoprienone SolutionImmediately start timing and when you get to your assigned time (x minutes)quench the reaction by precipitating out the crude reaction product by additionof the cold acidified water mixture. Transfer the contents of the conical flaskSolution I One go totheConica TiaSK.to a 250ml separating funnel and wash with an aliquot of diethyl ether (50ml).Run off the aqueous layer into a clean beaker, and collect the organic etherlayer in a conical flask. Replace the aqueous layer into the separating funnel3and re-extract with a second fresh aliquot of diethylether (50ml). Discard thespent aqueous layer and combine the ether layer in the separating funnel.Wash the ether layer with a fresh aliquot of distilled water (50ml), remove thewashing and transfer the organic layer into a clean 250ml conical flask. Drythe organic layer over anhydrous magnesium or sodium sulphate. Filter offthe drying agent through a fluted filter paper and collect the filtrate directly in around bottomed flask (placed on a cork ring).Remove the ether solvent by rotary evaporation under reduced pressure(consult the demonstrator about this technique).The groups need to record the IR spectra of the starting material and thecrude products from each of the different reduction times. Compare andcontrast the spectra and comment upon the optimum time needed to effectreduction under the reaction conditions used.QuestionsOther metal hydrides may be used to reduce-CArDony Lompounds forexample lithium aluminium hydride, Draw the structure and state thenamo of te reaction producrs If this reargen-wre-ueea to reduce eachof the following.b) ethyletnanoate2. Carbon carbon multiple bonds (double or triple) are not normallyreduced by metal hydrides. State the reagents and conditions requiredto bring about reduction of each of the following:а)cyclohexeneсуyclohexaneb)pent-2-yne→ cis-pent-2-ene1 PreviousNext3000DashboardCalendarТо-doNotificationsInboxLO

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2. Carbon carbon multiple bonds (double or triple) are not normally reduced by metal hydrides. State the reagents and conditions required to bring about reduction of each of the following: a) cyclohexene cyclohexane b) pent-2-yne → cis-pent-2-ene

2. Carbon carbon multiple bonds (double or triple) are not normally reduced by metal hydrides. State the reagents and conditions required to bring about reduction of each of the following: a) cyclohexene cyclohexane b) pent-2-yne → cis-pent-2-ene

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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