Sodium Borohydride Reduction of Benzil
6 Pages

Sodium Borohydride Reduction of Benzil

Course Number: CHEM 238, Spring 2008

College/University: UAB

Word Count: 636

Rating:

Document Preview

Sodium Borohydride Reduction of Benzil Raymond Oldham, Michael Lester, Audrey Paulzak CH-238 QZ Introduction: There are several methods to reduce aldehydes and ketones to alcohols. Both primary and secondary alcohols can be created by using complex metal hydrides such as lithium aluminum hydride and sodium borohydride, with ketones reducing to secondary alcohols and aldehydes reducing to primary alcohols. Both...

Unformatted Document Excerpt
Coursehero >> Alabama >> UAB >> CHEM 238

Course Hero has millions of student submitted documents similar to the one
below including study guides, practice problems, reference materials, practice exams, textbook help and tutor support.

Course Hero has millions of student submitted documents similar to the one below including study guides, practice problems, reference materials, practice exams, textbook help and tutor support.

Borohydride Sodium Reduction of Benzil Raymond Oldham, Michael Lester, Audrey Paulzak CH-238 QZ Introduction: There are several methods to reduce aldehydes and ketones to alcohols. Both primary and secondary alcohols can be created by using complex metal hydrides such as lithium aluminum hydride and sodium borohydride, with ketones reducing to secondary alcohols and aldehydes reducing to primary alcohols. Both reagents provide an abundant source of H+ ions that serve as catalysts for the reduction. Between the two reducing agents, lithium aluminum hydride (LiAlH 4) is extremely strong, expensive, and must be used in aprotic solvents. On the other hand, sodium borohydride (NaBH4) is inexpensive and can be used in common solvents such as water and alcohols. Also, all four of the hydrogen atoms can reduce the ketone or aldehyde1. In this experiment, sodium borohydride will be used to reduce diketone benzil in a quick and efficient manner. Table of Reagents: Melting Point (C) 94-95 400 d. -114.3 0 148.5-149.5 137-139 122-123 Molecular Weight (grams/mol) Benzil Sodium Borohydride Ethanol Water Hydrobenzoin (S,S or R,R) Hydrobenzoin (meso) Hydrobenzoin (racemic) 210 37.83 46.07 18.02 214.27 214.27 214.27 Mechanism: O + H H B H H - O + Na O O H BH2 - O - O BH2 H2O O B H2 - O H + HO OH Safety Information: - If any reagents come into contact with your body, wash with plenty of water. - Dispose of excess reagents in labeled containers. Procedure: To begin the experiment, 50.01 mg of benzil and 0.52 mL of ethanol were combined in an Erlenmeyer flask, and swirled gently until the benzil dissolved completely. The vial was then cooled in an ice bath, and 12 mg of sodium borohydride was added to the contents of the flask. The flask was swirled continuously for 10 minutes while the reaction proceeded. It was observed that the solid particles took a couple of minutes to dissolve. After ten minutes, 0.48 mL of water was added drop-wise to the mixture. Foaming occurred at the top of the solution for approximately one minute after the water was added. The mixture was heated a on hot plate until it came to a rolling boil, and then removed from the heat. Approximately 1.78 mL of hot water was added dropwise to the mixture. The amount added was determined by the clarity of the solution. As soon as it turned, and remained, cloudy, the addition of water was terminated. The flask was set aside to cool to room temperature, and allow crystal product to form. Once the solution had reached room temperature, it was placed in an ice bath to further crystallization of the product. The product was then collected through suction filtration. A melting point was determined after the product was completely dry. Results and Discussion: Since benzil is the limiting reactant in our sodium borohydride reduction of a ketone experiment, use the 50.01 milligrams to calculate the expected moles of product for the theoretical yield. Theoretical Yield = 50.01 mg reactant 1 mol reactant 1 mole product 210.22 grams 1 mole reactant 214.27 g product 1 mole product 50.97 mg product Where the "reactant" represents benzil, and "product" represents hydrobenzoin. The percent yield can then be calculated by using the actual weight of product and the theoretical yield. Percent Yield = Experimental weight of product Theoretical Yield 100 = Benzil Hydrobenzoin (meso) Theoretical yield Experimental yield Percent yield Melting Point 50.01 mg 20.02 mg 50.97 mg 20.02 mg 39.28% 136-138 C The product of this experiment was the meso hydrobenzoin, as indicated by the nearly identical melting point to the accepted values given by the lab manual1. REASONS FOR ERROR. DRAWINGS OF DIFFERENT CHIRALITY. 1. R,R AND S,S 2. MESO 3. RACEMIC Questions: 1) Benzil 1,2-diphenylethanedione Benzoin 2-hydroxy-1, 2-diphenylethanone Hydrobenzoin 1, 2-diphenylethane-1, 2-diol O OH Benzoin has the structure 2) 1.00 g Benzil 1 mole Benzil 1 mole NaBH 4 210.22 g Benzil 2 mole Benzil 37.83 g NaBH 4 1 mole NaBH 4 0.0899 g NaBH 4 Reference: 1. "Experiments in Organic Chemistry," R. Hill and J. Barbaro, Contemporary Publishing Company of Raleigh, Inc 3 rd Edition. (2005)

Find millions of documents on Course Hero - Study Guides, Lecture Notes, Reference Materials, Practice Exams and more. Course Hero has millions of course specific materials providing students with the best way to expand their education.

Below is a small sample set of documents:

UAB - CHEM - 238
Sodium Borohydride Reduction of Benzil Raymond Oldham, Michael Lester, Audrey Paulzak CH-238 QZIntroduction: There are several methods to reduce aldehydes and ketones to alcohols. Both primary and secondary alcohols can be created by using complex
UAB - CHEM - 238
Y1dUE 1ft-i. til. 5DMPUFlIED CORRELATION TABU:TYPE OF VIBRATIONC-H Alkanes -CH 3 -CH zAiken" (stretch) (bend) (bend) (stretch) (bend) Aromatics (stretch) (out-of-plane bend) (stretch) Alkyne Aldehyde Alkane Alkene Aromatic Alkyne Aldehyde Ketone Ca
Indiana - PSYCH - 102
P102 Exam 1 Review Notes Important definitions and concepts Chapter 1 (Lectures 1 and 2) -Psychology: the scientific study of the mind and behavior. -Behavior: observable response and actions. -Mind: internal processes and states that cannot be obs
Indiana - BUS-X - 100
1) Balance of payments deficit occurs when a. The net outflow of $ from a country exceeds the net inflow of $ from abroad. 2) Bonus Question what is the current index/value of the Dow Jones industrial avg. will be between 900 and 1200 (just find the
Indiana - BUS-X - 100
X-100 Study GuideStatement of Cash Flows explains financial changes that occur in a company from one accounting period to the next. Balance Sheet shows the company's financial position on a particular date. Balance of Payments the inflow and outf
Indiana - BUS-X - 100
X100 Key WordsTime management basic management of time is the need to know what time it is and what's on your agenda for the day. Qualification of candidate for promotionManagement styles Autocratic - Makes decisions alone - Intolerant of input fro
Indiana - BUS-X - 100
Marketing Marketing Plan conception, pricing, promotion, and distribution Marketing Mix combination of the "4 P's" of marketing: Product, Price, Promotion, and Distribution Market Segmentation dividing the total market into groups with similar cha
FIT - CVE - CVE 2080
Lab #3: Taping Over Uneven GroundJanuary 29, 2008; February 5, 2008 Gustavo Quiroz Victoria Nicastro, Ashley Dawn Chastain, Tim CVE 2080 Construction Measurements Lab Section 02Introduction: The purpose of this lab was to learn how to tape accura
UAB - CHEM - 238
The Aldol Condensation Preparation of Dibenzalacetone Raymond Oldham, Michael Lester, Audrey Paulzak CH-238 QZIntroduction This reaction gets its name from the reaction of a conjugate base of an aldehyde or ketone with the carbonyl group of either
UAB - CHEM - 238
The Diels-Alder Reaction Michael Lester, Raymond Oldham, Audrey PaulzakCH 238-QZIntroduction A Diels-Alder reaction is an example of an type of reaction called a cycloaddition reaction. This reaction is the process of combining the conjugated -sy
UAB - CHEM - 238
The Perkin Reaction Synthesis of a-Phenylcinnamic Acid Michael Lester, Raymond Oldham, Audrey Paulzak QZ-238Introduction The Perkin reaction is a condensation reaction similar to the aldol condensation reaction, except that it is between an aromati
UAB - CHEM - 238
CH 236 Final Exam Study Guide This guide is a list of major points that you should know from each experiment. You should read through all of the technique sections and the experiment sections in your lab manual that are listed in the syllabus. Also u
UAB - CHEM - 238
Audrey Paulzak Pre-LAB Experiment 6 PREPARATION OF DIPHENYLACETYLENEINTRODUCTION: A standard method for creating a carbon-carbon triple bond is demonstrated in this experiment. Add bromine to the carbon-carbon double bond of an alkene, followed by
FIT - CVE - CVE 2080
Lab #4: Differential Leveling02/05/08, 02/12/08 Gustavo Quiroz Ashley Dawn Chastain, Victoria Nicastro CVE 2080 Construction Measurements Lab Section 02Introduction: The purpose of this lab was to determine the elevation differences that were in
S. Indiana - BIOL - 105
BIOLOGY 105 Spring 2008 Syllabus Instructor: Mr. Chandler WalkerText: Human Biology Concepts and Current Issues 4th Edition Michael D. Johnson Lab Manual Human Biology Concepts and Current Issues 4th Edition B. - Atsma & S. Hsu E-mail address: cwa
S. Indiana - BIOL - 105
BIO 105 EXAM 2 Study Guide Spring 2008 (Walker) Exam 2 will be held next Wednesday, March 5th. It will be similar in format to Exam 1, so bring number 2 pencils. The exam will cover Chapters 7, 8, and 9. Chapter 7 C.V. System: Blood Learn the diffe
SUNY Buffalo - ECO - 181
Comparative Advantage: The Basis for ExchangeMBMCMB MCComparative Advantage: The Basis for ExchangeWhat Do You Think?Do the Nepalese perform their own services because they are poor or are they poor because they perform their own servi
FIT - CVE - CVE 2080
Lab #5 Differential Leveling-Part 22/18/08, 2/25/08 Gustavo Quiroz Ashley Dawn Chastain, Victoria Nicastro CVE 2080 Construction Measurements Lab Section 02Introduction: The purpose of this lab was to use a self level and a rod to be able to take
Missouri (Mizzou) - ART HISTOR - 3000
3/6/08 19th cen Art Notes I. Jericho a. Synthetic artist- combines several different strands of artistic activities b. Died young- not tons of paintings c. Trains with Gerand, takes it upon himself to learn through experience (unconventional, based o
SUNY Buffalo - ECO - 181
Economic Growth, Productivity, and Living StandardsMBMCMB MCIntroduction"Which would you rather be? An ordinary, middleclass American living today, or the richest person in America at the time of George Washington?"Copyright c 2007 by Th
SUNY Buffalo - ECO - 181
Measuring Economic Activity: GDP and UnemploymentMBMCMB MCIntroduction"Real GDP, the value of goods and services produced in the U.S., grew at an annual rate of 1 percent in the fourth quarter."Copyright c 2007 by The McGraw-Hill Compani
FIT - CVE - CVE 2080
Lab #6 Topographic Survey of the Traverse Course2/19/08, 2/29/08 Gustavo Quiroz Ashley Dawn Chastain, Victoria Nicastro CVE 2080 Construction Measurements Lab Section 02Abstract: The goal of this lab was to calculate elevations at points on a gri
Incarnate Word - HIST - 1301
Survey of World History to 1550 Professor John Boswell 5 December 2006 The Great Mortality Kelly, John A. The Great Mortality. New York: Harper Perennial, 2005. The Great Mortality serves to inform readers of the movement and destruction of the Black
Incarnate Word - EDUC - 2305
Foundations of Education Dr. David Campos 14 February 2008 Critique #1 Source: Intrator, Sam M. "The Engaged Classroom." Educational Leadership 62.1 (2004): 20-24. In this article, Sam Intrator discusses what teenagers are currently experiencing in t
Missouri (Mizzou) - ART HISTOR - 3000
Anthropology Notes 1/23/08 I. Scientists a. Lamarck: introduced the taxonomic distinction between vertebrates and invertebrates. His theory that the acquired characteristics of a species could be inherited by later generations was a forerunner to Cha
Missouri (Mizzou) - ANTHRO - 2050/2
Notes for Exam 2 3/10/08 I. Human Variation and Disease a. How does using an evolutionary perspective help us to understand human disease? b. How do you use an evolutionary perspective? c. Human disease ecology: Understanding the role of environmenta
Missouri (Mizzou) - ART HISTOR - 3000 WI
Contemporary Art Notes Avant-garde: Minimalist art: 60s (same time as pop art) Marriage of reasons? Repitition to composition: principle determined by set of instructions/algorithm, strong and hand made component, painted in black leaving lines expos
FIT - CVE - CVE 2080
QUIZ 10 1. What are two types of horizontal curves? Spiral, circular 2. What type of curve will cause increasing centifugal force if the vehicle maintains constant speed? (This answer was not corrected on the quiz I am typing up. Look it up so you ca
FIT - CVE - CVE 2080
QUIZ 11 1. Vertical curves are typically what type of curve? Parabolic 2. What methods are available to layout a vertical curve? Offset tangent 2. What does BVC, VPI, and EVC stand for? Beginning Vertical Curve Vertical Point of Intersection Ending V
FIT - CVE - CVE 2080
QUIZ 9 1. Name some equipment used in construction surveys. GPS receiver, level, tape 2. How can you stake out a pipeline, when construction requires you to dig up the location where the pipeline will be placed? Use offsets 3. When staking out a buil
FIT - CVE - CVE 2080
QUIZ 5 Chapter 9 1. Name three methods that traverse angles can be measured. Interior angles Deflection angles Angles to the right A2 Azimuths 2. What two types of measurements must close to determine if a traverse closes? Angular closure/geometric c
FIT - CVE - CVE 2080
QUIZ 6 1. What is a sounding? Depth measurement from the surface of water to the bottom. 2. What is a breakline? Topographical survey that deligates between 2 intersections thus promoting the same slope and a uniform grade. 3. Topographic surveys req
Clemson - ECON - 352
SUNY Buffalo - ECO - 181
Workers, Wages, and Unemployment in the Modern EconomyMBMCMB MCIntroductionWhat Do You Think?Has everyone benefited equally from economic growth and increased productivity?Copyright c 2007 by The McGraw-Hill Companies, Inc. All rights
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 5Section 5.11. a. b. c. P(X = 1, Y = 1) = p(1,1) = .20 P(X 1 and Y 1) = p(0,0) + p(0,1) + p(1,0) + p(1,1) = .42 At least one hose is in use at both islands. P(X 0 and Y 0) = p(1,1) + p(1,2) + p(2,1) + p(2,2) = .70 By summing row probabi
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 6Section 6.11. a. We use the sample mean,x to estimate the population mean .^ =x=b.xi 219.80 = = 8.1407 n 27We use the sample median, ascending order).~ = 7.7 (the middle observation when arranged in x1860.94 - ( 219.8) 27 s =
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 7Section 7.11. a.z 2 = 2.81 implies that 2 = 1 - (2.81) = .0025 , so = .005 and the confidencelevel is 100 1 -()% = 99.5% .b. c.z 2 = 1.44 for = 2[1 - (1.44)] = .15 , and 100(1 - )% = 85% .99.7% implies that = .003 , 2
Oklahoma State - ANSI - 3423
Write your name on the back of the last pageExam 3 November 5, 2004 ANSI3423 Animal Genetics(60) MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) After a region of DNA has been replicated,
Oklahoma State - ANSI - 3423
Write your name on the back of the last pageExam 1 September 17, 2004 ANSI3423 Animal GeneticsMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) A genetic cross in which the inheritance of t
Oklahoma State - ANSI - 3423
Write your name on the back of the last page Exam 2 October 8, 2004 ANSI3423 Animal Genetics MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) The mitochondrial genome contains genes that enco
Oklahoma State - ANSI - 3423
Write your name on the back of the last pageFinal Exam, Dec. 15 2004 ANSI3423 Animal GeneticsMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which of the following is a characteristic of r
Oklahoma State - ANSI - 3423
Chapter 14 Study GuideThe material in this page is only a guide to help you prepare for the exam. You are responsible for knowing material covered in the class and for having read the relevant chapter in the text.Concepts to know: alpha helix, ami
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 8Section 8.11. a. b. c. d. Yes. It is an assertion about the value of a parameter. No. The sample median~ X is not a parameter.No. The sample standard deviation s is not a parameter. Yes. The assertion is that the standard deviation of
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 9Section 9.11. a.E (X - Y ) = E( X ) - E (Y ) = 4.1 - 4.5 = -.4 , irrespective of sample sizes.V ( X - Y ) = V (X ) + V (Y ) =of2 12 2 (1 .8) (2.0) = .0724 , and the s.d. + = + m n 100 100 2 2b.X - Y = .0724 = .2691 .c.A norm
Pittsburgh - PSY - 0010
Exam 4 Study Guide Chapter 14- Stress & Health Behavioral medicine- an interdisciplinary field that integrates behavioral and medical knowledge and applies that knowledge to health and disease. Health Psychology- a subfield of psychology that provide
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 10Section 10.11. a. Ho will be rejected iff F.05, 4,15 = 3.06 (since I 1 = 4, and I ( J 1 ) = (5)(3) = 15 ).The computed value of F isf = 3.06 , Ho is not rejected. The data does not indicate a difference in the mean tensile stre
Pittsburgh - ECON - 0100
Nicole Ionadi Econ 0100 Recitation Friday at 1 Nmi5@pitt.edu How Far Will Retailers Go to Keep Holiday Business Booming? With the holiday season quickly approaching, one thing is on everyone's mind: shopping for the perfect holiday gift. No one knows
Pittsburgh - ENGCMP - 0200
Nicole Ionadi EngCmp 0200 MWF 2-2:50 Nmi5@pitt.edu McClanahan's Sentences: 1. Whatever had held us together in high school intramural sports, glee club, the senior-class play- was light-years away. 2. Over the next weeks I started taking long drives
Pittsburgh - FR - 0003
Nicole Ionadi La Moderne Histoire FR 003 MWF 12-12:50 Nmi5@pitt.edu L'Anneau d'Amour Il y avait un chmeur qui s'appelle Guy, dans un train. Il essayait arriver une nouvelle place qu'il considrera son maison. Pendant il tait sur le train, il trouvait
Pittsburgh - PSY - 0010
Psychological Disorders -What is normal? \ -What is `abnormal'? / very complex concept.operates on continuum. Thoughts Feelings Behaviors What do we look at when determining normal or abnormal? 1. Violation of or deviation from social/cultural norms?
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 11Section 11.11. a.30.6 59.2 7.65 = 7.65 , MSE = = 4.93 , f A = = 1.55 . Since 1.55 is 4 12 4.93 not F. 05, 4 ,12 = 3.26 , don't reject HoA . There is no difference in true average tire MSA =lifetime due to different makes of cars.b.
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 12Section 12.11. a. Stem and Leaf display of temp: 17 0 17 23 17 445 17 67 17 18 0000011 18 2222 18 445 18 6 18 8stem = tens leaf = ones180 appears to be a typical value for this data. The distribution is reasonably symmetric in appeara
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 13Section 13.11. a.2 ^i is 10 1 - 1 - (x i - 15 ) = = 250 , so s.d. of Yi - Y 5 250x = 15and (xj- x)26.32, 8.37, 8.94, 8.37, and 6.32 for i = 1, 2, 3, 4, 5. b. Nowx = 20 and (xi- x ) = 1250 , giving standard deviation
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 14Section 14.11. a. We reject Ho if the calculated 2 value is greater than or equal to the tabled value of2 , k -1 from Table A.7. Since 12.25 .2 , 4 = 9.488 , we would reject Ho . 05b. c. d.Since 8.54 is not Since 4.36 is not
Clayton - CHEM - 1151L
DATA SHEETDate April 8, 2008 Atmospheric Pressure Mass of Mg Water Vapor Pressure(See Table 1)Name Partner Room .040g Temp Volume H2 21.1mm Hg 41.61mLShannon Polson JustinRoom 23C Temp Volume H2296K .04162LShow your work for each of the c
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 15Section 15.11.H 0 : = 100 vs. H a : 100 . The test statistic is s + = sum of the ranks associated with the positive values of ( xi - 100) , and we reject Ho at significance level .05 if s + 64 . (from Table A.13, n = 12, with / 2 =
Rensselaer Polytechnic Institute - ENGR - 2600
CHAPTER 16Section 16.11. All ten values of the quality statistic are between the two control limits, so no out-of-control signal is generated.2.All ten values are between the two control limits. However, it is readily verified that all but one
Clayton - CHEM - 1151L
REPORT SHEETDate April 8, 2008 Atmospheric Pressure Name Partner Shannon Polson JustinInclude with this report sheet the data sheet and all calculations. Be sure everything is complete. 1. The weather stations give the atmospheric pressure in inch
Clayton - CHEM - 1151L
DATA SHEETDate March 31, 2008 Reactions of Copper Initial weight of copper: 1.004 Name Partner grams Shannon Polson Justin and BrendaFor the following observations, indicate and describe the formation of any precipitates (see your textbook). Also,
Clayton - CHEM - 1151L
REPORT SHEETDate March 31, 2008 Reactions of Copper Include with this report sheet your data sheet. Answer the following questions: 1. Charles ended with less than 100% copper recovered. Assuming that he used the balances correctly and did the mathe
Rensselaer Polytechnic Institute - ENGR - 2600
ENGR-2600 Modeling and Analysis of UncertaintyENGR-2600 Modeling and Analysis of Uncertainty To Access the Detailed Course Outline you can sign on WebCT at:http:/rpilms.rpi.edu/webct/entryPageIns.dowebct If you have trouble signing on, please re