WITTIG REACTION. Solo Experiment 2 Individual Lab Report (due at 12:00 pm one week after the lab is performed)

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1 WITTIG REACTION Solo Experiment 2 Individual Lab Report (due at 2:00 pm one week after the lab is performed) Last Name: Atique First Name: Anika TA Name: Davin Date Lab Performed: 2/26/204 Date Lab Submitted: 5/2/204 Group A, B, or C: B Comments for Grading TA: (Please indicate if you performed the lab on a day other than your regularly scheduled day and/or with a TA other than your regular TA). Page Limit: report must not exceed FIVE pages (including this page) (Please see General Lab Report Guidelines for detailed descriptions of all other requirements) ** Deductions for handwritten report/structures/graphs and exceeding page limit **

2 ** Late penalty is 2 marks per day late ** 2

3 Experiment 3: Wittig Reaction Lab Report Guidelines Include the following in your report (in the following order, use provided table):. Objective: ( mark) What is the purpose of this experiment? The purpose of this lab is to make an alkene, ethyl cinnamate using a stabilized ylide and benzaldehyde via wittig reaction 2. Introduction: (2 marks) Brief description of the concept/reaction studied Wittig Reaction and its impact/importance The first step in witting reaction is the synthesis of the ylide. We can either have stabilized or nonstabilized ylide and this depends on whether there is an electronegative element in the moleculein conjugation to stabilize the negative charge on the carbon. To make the ylide a phosphine, Ph3P, is reacted with an alkyl halide (tertiary alkyl halide doesn't work) and a SN2 reaction takes place. Then we use a base to deprotonate the carbon bonded to Ph3P to obtain the ylide. The base used depends on the acidity of the proton bonded to the carbon, the presence of an electron withdrawing group makes the proton more acidic so we can use a weaker base such as NaOH, KOH etc. In the absence of an electron withdrawing group we use a stronger base like NaH, NaNH2 etc. In the witting reaction the ylide reacts with an aldehyde or ketone to form an alkene and phosphine oxide. A stabilized ylide will give us the trans alkene which is the thermodynamic or more stable product and the nonstabilized ylide will give the cis alkene which is the kinetic product. Witting reaction is important because it allows us to couple two carbon fragments together to form a new C=C bond. Alkenes are very important starting material for a lot of industrial reaction. Also, witting is specific for aldehydes and ketones this allows us to carry out the reaction in the presence of other functional groups in the molecule. 3. Reaction Scheme: (2 marks) Bal anced chemical equation and data [molar mass, concentration, density, volume, mass, moles, etc as appropriate including theoretical yield] for reactants and products

4 Materials Benzaldehyde Ylide Hexanes Alkene Molar Mass/ g Quantity 0.00mL 0.348g ml Density/ (g/ml) Moles Theoretical yiled 0.76g 4. Procedure: (2 marks) Summary of lab procedure what YOU did, include KEY observations be concise! I added 0. ml benzaldehyde and.348 g ylide to a 25mL round bottomed flask. Mixed the contents until the ylide dissolved and a white precipitate appeared and then added 7 ml hexane. I swirled the flask and then did gravity filter to remove the precipitate and obtain the solution. The solution was collected in another 25 ml round bottom which I had previously weighed. I evaporated the solution using a rotary evaporator until all the hexane was removed and little beads of clear liquid was stuck to the flask. I took the final weight of the flask to find the yield. Lastly, I did an IR of the product. 5. Results: (5 marks) a. Table : Yield and Physical Properties Crude Wittig Product Yield (g).60g Yield (%) 9% Appearance While liquid b. Figures: IR and NMR Spectra i. IR Spectrum of Wittig product attach and label important stretching frequencies 4

5

6 ii. H NMR Spectrum of Wittig product assign the major peaks labeled on the NMR (A E) by filling out the following table (as an example the aromatic signals are already filled out). Label the Hs on the structure below as HA, HB, HC, HD, HE (HB already done!). Scan/upload annotated spectrum show your calculation for coupling constants on the spectra. Label A B C D E Peak Position (ppm) Multiplicity doublet multiplet doublet quartet triplet Coupling Constant(s) Hz Observed Integration Number of Hydrogens Discussion: (8 marks) a. Discussion of Yield chemical reasons for less than 00%? Acetone was used to rinse out the flask before the reaction so, some of the ylide could have reacted with the acetone to give a different alkene as a side product, as a result not all the ylide reacted with the benzaldehyde and we got an yield less than 00% b. Discussion of Product Data evidence for correct product i. Analysis of IR spectrum diagnostic signals? The CH stretch for benzaldehyde alone wouldn't have peaks below 3000 because it only has SP2 hybridized orbitals. However the IR spectrum of the product shows peaks below 3000, this is due to the SP3 orbitals of the ethyl portion of the ester in the alkene product. The CO peak in the IR is in the 200 region, this is also characteristic 6

7 of as ester, if it was only the benzaldehyde the peak would have been closer to 00. The carbonyl peak is also higher than it would have been for an aldehyde alone. ii. Analysis of H NMR spectrum diagnostic signals that indicate trans alkene has been formed The coupling constant for the protons A and C are 6.4 and 5.84 respectively. this is characteristic of a trans alkene. If the product was cis then the value would have been in the 50 region. For trans it's 28. ALSO, identify the compounds responsible for the minor peaks in the H NMR spectrum (ie. the peaks not labeled AE), chemical shifts listed below: 0.02 ppm benzaldehyde (HCO) 7.26 ppm solvent d3 cfloroform ppm cis ethyl cinnamate ppm cis ethyl cinnamate.26 ppm hexanes 0.88 ppm hexanes c. Mechanism detailed mechanism for the Wittig reaction of your reactants

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