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Analyst Dane 127 126 124 122 120 118 116 114 112 110 se 108 106 104 102 100 98- 96 94 92 4000 3500 Teaching Tuesday, July 05, 2022 12:47 PM 2966-1,293%T 3000 2500 cm-1 Teaching 4999 Sample 4999 By Teaching Dale Tuesday, July 5 2022 2000 150x340-3,11% ST Peton 1241 29 117.3INT PAT 173 18237301111 24 Mo 1654042 153852 13003m 1. INT 1500 My 16,2 124 P 821093 VKY The Mans 106 ONT CHANT 101 10 855 30cm 100% 1000 415 500400 # Questions to be Addressed in Your Results/Analysis 1) From the spectral data (H, IR, MS) you were given, identify the structure of your product. Explain why you chose your particular product based on the spectroscopic data. You will not receive full marks for determination of the unknown unless you explain why. 2) Based on your IR data, how would you rate the purity of your product? Are there any significant impurities, and if so, what is/are it/they? Postlab Questions 1) The reaction you actually perform in this experiment has some complexity in the mechanism, but you can analyze a simple two step version. Draw the arrow-pushing mechanism of the condensation reaction to form an imine using methylamine and acetaldehyde. 2) Draw the arrow-pushing mechanism of the second step of the reductive amination mechanism to convert the imine from Q1 to an amine using sodium borohydride. 3) Reductive amination is an important reaction in biology that is used to install nitrogen onto biomolecules. Name a major class of biomolecules that are prepared via reductive amination? 07105
Experiment 2- Reductive Amination of Unknown Aldehydes and Amines Reading: http://www.organic-chemistry.org/synthe ... /reductive amination.shtm Introduction Containing Molecules Amines are an important class of compounds, finding Figure 1. Biologically-Relevant Nitrogen applications in numerous pharmaceuticals, as well as prominently featuring in many petrochemicals and materials (Figure 1). They are also an important building block for synthetically and medicinally-valuable heterocycles. There are as a result a plethora of synthetic approaches to convert compounds into amines, or to react functional groups with other amines to make more complex amine products. Amines can themselves be oxidized into numerous functional groups, such as nitroso, diazo, or nitro groups. An especially important class of reactions related to amines are condensation reactions between amines and aldehydes and ketones. The product imines are also known as Schiff bases. Although Schiff base formation is R-NH₂ 1 Amine Aldehyde Figure 2. Reaction and Subsequent Reaction of Grignards with Esters a) Reductive Amination Between Primary Amine and Aldehyde R-N Imine (Aldimine) b) Reductive Amination Between Secondary Amine and Aldehyde -R -R R R-N- R Iminium R-N R 2 Amine 3 Amine c) Reductive Amination Between Primary Amine and Ketone 0 R₁ R R NH R H -R Reductant FR R-NH 2 Amine R R-NH₂ 1 Amine Ketone Reductant -R Reductant R R-NH. 2 Amine Diphenhydramine Antihistamine O,PO OH NH₂ Sphingosine-1-Phosphate Signaling Lipid Diazepam Anti-Anxiety H₂N OH Glycine Amino Acid reversible, the intermediates can be reduced to generate amines with an additional substituent (Figure 2). Aldehydes are more reactive than ketones in the condensation reaction, and oftentimes very harsh conditions are required to drive condensations with ketones. As such, secondary amines are commonly prepared via reductive amination with aldehydes, but rarely with ketones. Secondary amines are generally not as reactive in these reactions as primary amines, because instead of making an imine, a highly electrophilic iminium is made. Again, dehydrating conditions can be R-N Imine (Ketimine) employed to help drive the reaction forward. Experiment After finishing your degree, you manage to land an interview with a pharmaceutical company. During your interview, you're asked what your favorite chemistry class was, and you mention you really enjoyed
Figure 3. List of Potential Unknowns a) Potential Unknown Amines NH₂ NH₂ NH₂ NH₂ Me Br Of b) Potential Unknown Aldehydes CHO CHO CHO NO₂ &&&& Name CI Unknown Aldehyde Unknown Amine sa a NO₂ Br Sodium Triacetoxyborohydride Dichloromethane CHO CHO CHO NMO₂ Br Br all of the reactions with unknowns that you got to run during your Organic lab (although it always seemed strange that you'd have so many experiments where you had no idea what your compounds were). The HR manager says that she's glad to hear, because the next part of your interview will entail taking an unknown aldehyde and amine, and performing a reductive amination reaction, followed by analyzing the product to determine what your unknowns were. Before you have time to be too upset by this pop quiz, however, you're given a list of the possible unknowns. Shew, that'll make things much easier. Prelab Questions 1) Based on the Material Safety Data Sheets (MSDS) for the compounds, which of the compounds in this experiment is the most hazardous, and why (you have been provided with the most hazardous of the unknowns, consider this to be representative of the whole set)? CHO H Formula ??? ??? مدیم 2) Finish filling in the reagent table and reaction scheme of your particular reaction in your lab notebook (You will have to leave parts of this blank until you determine your unknowns). Figure 4. Generic Reductive Amination Procedure NaBH(OAc) R-NH₂ Mol.-eq. ??? ??? ? CHO Mw ??? ??? NH₂ mmol ??? 222 R CHO Density/Conc. ??? 722 Amount 222 222 163 mg 2 ml ??? ??? ??? ??? ??? Product 3) If the reaction doesn't go to completion, you may have aldehyde starting material present, or you may have the by-product alcohol (from reduction of the aldehyde). How would you identify these impurities most easily by H NMR? 4) How would you identify an aldehyde by IR spectroscopy? Procedure 1. Reaction Set-up
You will be assigned an aldehyde and an amine by your TA. The mass or volume (for liquids) that you will need to measure for each will be listed on the bottle. Make sure to write this down in your lab notebook! Add your unknown aldehyde, amine, sodium triacetoxyborohydride (163 mg), and methylene chloride (2 mL) (in that order) to a dry 10 mL round bottomed flask equipped with a magnetic stir bar. Transfer the flask to a stirplate and stir the reaction for 2 h. You can use TLC to monitor the reaction. If either the aldehyde or amine is fully consumed, you can stop the reaction early. Keep in mind that you may need to use both UV/Vis and phosphomolybdic acid stain to fully visualize your TLC plate. You can check with TLC every 30 minutes, and the plate should be developed using 1:1 ethyl acetate/hexanes. 2. Isolation and Purification of Product After the reaction is complete, quench with saturated. aq. sodium bicarbonate solution (5 ml) and transfer to a separatory funnel. Add an extra 10 mL dichloromethane to the separatory funnel to make the separation easier. Separate the organic (lower) layer and place it in a 50 mL Erlenmeyer flask. Wash the retained (upper) aqueous layer with 5 mL methylene chloride. Remove the aqueous layer from the separatory funnel, then combine the two organic layers and return them to the separatory funnel. Wash with sat. aq, sodium bicarbonate (5 mL), then brine (5 mL). Transfer the organic layers to the 50 mL Erlenmeyer and dry over sodium sulfate. Remove the sodium sulfate via gravity filtration. Discard the solid and transfer the solution to a preweighed flask or beaker, then evaporate the solvent under gentle heating. Some of the products have low boiling points (~90 "C), so be careful to not evaporate all of your product off while removing the solvent. 3. Analysis of Product Weigh your product, and take the IR. You will be provided with ¹H NMR and MS data on Blackboard. Questions to be Addressed in Your Results/Analysis 1) From the spectral data (¹H, IR, MS) you were given, identify the structure of your product. Explain why you chose your particular product based on the spectroscopic data. You will not receive full marks for determination of the unknown unless you explain why. 2) Based on your IR data, how would you rate the purity of your product? Are there any significant impurities, and if so, what is/are it/they? Postlab Questions 1) The reaction you actually perform in this experiment has some complexity in the mechanism, but you can analyze a simple two step version. Draw the arrow-pushing mechanism of the condensation reaction to form an imine using methylamine and acetaldehyde. 2) Draw the arrow-pushing mechanism of the second step of the reductive amination mechanism to convert the imine from Q1 to an amine using sodium borohydride. 3) Reductive amination is an important reaction in biology that is used to install nitrogen onto biomolecules. Name a major class of biomolecules that are prepared via reductive amination?
Analyst Dane 127 126 124 122 120 118 116 114 112 110 se 108 106 104 102 100 98- 96 94 92 4000 3500 Teaching Tuesday, July 05, 2022 12:47 PM 2966-1,293%T 3000 2500 cm-1 Teaching 4999 Sample 4999 By Teaching Dale Tuesday, July 5 2022 2000 150x340-3,11% ST Peton 1241 29 117.3INT PAT 173 18237301111 24 Mo 1654042 153852 13003m 1. INT 1500 My 16,2 124 P 821093 VKY The Mans 106 ONT CHANT 101 10 855 30cm 100% 1000 415 500400 # Questions to be Addressed in Your Results/Analysis 1) From the spectral data (H, IR, MS) you were given, identify the structure of your product. Explain why you chose your particular product based on the spectroscopic data. You will not receive full marks for determination of the unknown unless you explain why. 2) Based on your IR data, how would you rate the purity of your product? Are there any significant impurities, and if so, what is/are it/they? Postlab Questions 1) The reaction you actually perform in this experiment has some complexity in the mechanism, but you can analyze a simple two step version. Draw the arrow-pushing mechanism of the condensation reaction to form an imine using methylamine and acetaldehyde. 2) Draw the arrow-pushing mechanism of the second step of the reductive amination mechanism to convert the imine from Q1 to an amine using sodium borohydride. 3) Reductive amination is an important reaction in biology that is used to install nitrogen onto biomolecules. Name a major class of biomolecules that are prepared via reductive amination? 07105
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