Lab 5 - Reductive Amination_AdjustedPostlab_2024

I. Look at the MS/MS for paracetamol (a drug), explain the peaks seen at 134 and 110, and draw the structure for the 110 peak. Paracetamòl N-(4-hydroxyphenyliacetamide ESI+, MS/MSs Kky pan_03_c80720211368 1-38 RT: 0.00024 AV 35 N: 107ES T TMSES F ms 12.00g24 00 0 00-10.0g 100g 110.0 CH но 70 (M.H]* 162.0 16 1340 130 100

Please identify compound 1 and compound 2!!! Attached is the H-NMR and IR for both compounds (ignore the IR peaks ~2400).  The experimental melting point for the aqueous layer was 260-261 celcius. The experimental melting point for the organic layer was 76.9-78.7 celcius.  The following was my procedure: IntroductionThe reaction mixture in this experiment contains 4-bromobenzaldehyde, methanol, and aqueous potassium hydroxide. A reaction occurs that produces two organic compounds, compound 1 and compound 2. Both are solids at room temperature. Your task is to isolate, purify, and identify both compounds. A specific procedure is given for preparing the compounds, but you will need to work out the procedures for most other parts of this experiment.Experimental ProcedureThis procedure should produce enough of each compound to complete the experiment; however, in some cases, it may be necessary to run the reaction a second time. Although this experiment can be done individually, it works…

4- Show (draw) or print or bring the 1H-NMR spectra and 13C-NMR spectra for methylphenyl ester.

19. For the following reaction, which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to the product? DMSO A. absorption at 3200-3600 cm should disappear B. absorptions at 3200-3600 cm and 1100 om should disappear C. absorption at 1100 cm should disappear, a new absorption at 3100 cm should appear D. absorption at 1720 cm should appear, absorption at 3200-3600 cm should disappear E. none of these O A O B O D O E

After the reduction of camphor with NaBH4 experiment, you took a 1H-NMR of your product sample. The sample ave the following 1H-NMR singlas with the given integrations (2.314 and 9.497). Determine the product ratio of isoboreneol to borneol in this particular mixture.

3- Show (draw) or print or bring the 1H-NMR spectra and 13C-NMR spectra for diethylETHER.

Post Lab Questions - Synthesis of Fluroscein 3.Explain why there are differences in absorbances (specifically wavelengths) of fluroscein and phenolphthalein. Which one would you expect to be a higher wavelength and why?

2. READ THE DIRECTIONS TO EACH QUESTION CAREFULLY - not following the directions means you get the question wrong! 3. FORMAT YOUR ANSWERS AS DIRECTED - formatting your answers incorrect means you get the question wrong! 4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems: ¹H NMR 12 R ΟΞΟ 11 10 PIC OH R H 9 8 7 ppm 6 OH H C=C-H 5 NH H-C-X H-C-O -OH X = F, Cl, Br (i.e. electronegative atom) 3 -NH 2 H-C-N H-C-S 1 -CH3 -CH₂- C=C-H H-C-C=O -CH H-C-C=C HC-0 0 4000 small range Hrange of values broad peak DID =C-H N-H 3250- 3300 broad with spikes -3300 3500 -O-H broad-3300 -3400 -O-H CEN usually strong N-H CIO C H ₹ -C-H O 2730- 2820 3000- 2 peaks 3100 2850- 2960 O -C-O-H broad-3000 3000 H -CEN 2500 wavenumber, cm-1 2200 <-CICH B 2200 2000 CC H.C. N 1680 000000 H 1600- 1660 0 OR 1730 1710 1600 NR₂ 1650 1500 1000

A student attempted to create the following conjugated compound via a double elimination. The mass spectrum showed the correct compound had been formed. And yet, the IR spectrum should definitive evidence that the wrong compound was formed. Answer using the bold letters. What do you think was formed ? Which functional group? A alcohols B alkyne C ketone D another functional group What peak was lacking from the IR spectrum that should have been there E 1500-1800cm1 F 2000-2500cm-1 G 3000-3500cm1 What peak was present in the IR spectrum that confirmed the wrong product H 1500-1800cm1 I 2000-2500cm1 J 3000-3500cm1 Br 2eq NaOH

Draw the correct structure from the MS, 1H NMR, 13C NMR, and IR data given below. Both of the peaks on the 1H NMR spectrum are doublets (J = 2.5 Hz) and the integration ratio is 1:1.

co select file Post-Lab Questions HW1. The following 'H NMR was taken for benzaldehyde. What diagnostic change(s) in the spectrum do you anticipate seeing for the NMR of the methyl cinnamate product? 12 11 10 9 Wittig Reaction 8 7 31 6 Name: 5 3 2 ppm th F12 } ]

5. Draw the structure that corresponds to the peaks labeled A – E for the mass spectrum of heptane. Circle and label the base peak, M* peak, and M+1 peak. 100- 80- 60- 40 20 Relative abundance A B с E 0 D- 20 40 60 80 100 120 m/z 6. Answer the following questions based on the mass spectrum shown below. Mal-Lippolis, Nesle CHEM 2423 Spring Mx mass spectrometry on The Mes Spectromex mass spectrometer Digital Resources for X S digitalnorton.com/47385 AppImported from Google Google Maps Dogle.com Som experiments Home Gym WOC Sign your a € CH16HW Rel. Intensity MASS SPECTRUM 100 80 60- 40 20- 35% 0.0+ 20 40 60 80 100 120 m/z NIST Chemistry WebBook (http://webbook.nist.gov/chemistry) lippolisn@wcjc.edu SUBMIT ANSWER A. Which peak is the base peak? B. Which peak is the molecular ion? c. What is the M + 1 peak? D. What is the M + 2 peak? E. What heteroatom exists in the above mass spectrum? F. What is the molecular formula?

Label all relevant peaks that are above the fingerprint region (>1500 cm-1) in all the IR spectra given below with the functional group that those peaks are representative of (make sure not to forget the aldehyde C–H bonds, which many IR charts do not list). Based on the table you completed with predicted Diagnostic IR peaks for each compound, and based on the IR spectra you had labeled, match each compound with its spectrum.

Look at the structure of ethyl acetate in your notebook. In which region of the 13C spectrum of ethyl acetate would you NOT expect any peaks?     a.0 - 50 ppm b.50 - 100 ppm c.100 - 160 ppm d.160 - 220 ppm

Properly annotate the NMR spectra of your unknown alcohol TFA ester. Make sure that you draw the structure of your parent alcohol on your spectra.

24. How can IR spectroscopy help to monitor the following reaction? OH e PCC a. What structural features distinguish the reactant from the product? b. What structural features would NOT help in distinguishing the two structures? C. What would you look for in the IR data of both structures? d. How would you know when the reaction was complete?

5. IR spectra: Identify and label the peaks relevant to your compound. R of 4-Aminophenol HIT-NO-1628 6CORE- I P-AMINOPHENOL 80BS-NO-1520 ER-NIDA-03620 : KBR DISC CHNO 2000 1000 VE Ral ID 1 I011 as 027 10 3141 19 3284 26 2001 48 2814 42 1476 12 138 41 1256 10 1240 11 1214 36 1170 29 1152 60 3160 52 a033 39 3007 43 2684 57 2596 36 2495 46 972 18 947 41 921 46 092 62 B46 62 752 13 707 se 647 sa 524 28 6IB 41 H2N- OH 2964 44 2920 42 I0IS 46 I612

What fragment is responsible for the base peak in the MS spectra of 4-phenyl-2-butanone, 1-phenyl-1-butanone, and 1-phenyl-2-butanone

Imagine that you were given an unidentified aldehyde and performed another Wittig reaction in lab. Use the given data to answer the questions below and identify your original aldehyde. 8 5 R A H 7 + 15 1 C/O (C6H5)3P- Below is shown the ¹H spectrum for the pure alkene product of this experiment. Interpret the signals to identify "R" by assigning each hydrogen by chemical shift, multiplicity (splitting), integration, and any other significant features. 6 A B -5 NaOH 4 PPM (b) One possible alkene product is shown in the reaction above. Draw the other alkene product R 3 H 2 + (C6H5)3PO 2 1 6 1 (a) Label which proton in the product above corresponds to each signal A and B. Explain your assignment and what this tells you about the "R" group. (c) What was your aldehyde starting material? (What is "R"?) 1

Part A - Multi-step Synthesis (n-butanol → 1-Bromobutane) 1) IR: discuss the IR, specifically how you can tell you made butyl bromide from n-butanol. Label and discuss key peaks on your spectrum. 2) NMR: assign peaks; discuss splitting and integration values.

5. NMR analysis: Triphenylmethanol| Draw the full structure of the product. Show all bonds to the hydrogens. Label the different sets of hydrogens (i.e. Ha. Hb, H1, H2, etc) based on which ones are equivalent and which ones are not. Assign each set of hydrogens with a specific signal on the spectrum. Create a table that summarizes: the chemical shift, integration, multiplicity, proton assignment, and justification of each signal.

(b) One possible alkene product is shown in the reaction above. Draw the other alkene product that could form from a modified Wittig, the Horner-Emmons reaction (p387). (c) What was your aldehyde starting material? (What is "R"?) 1

2) On spectra 2 are the mass, IR and 13 C and 1 H NMRspectra of an organic compound.a) From these spectra, determine the structure of the molecule. Rememberto ignore the triad in the 13 C NMR spectrum at 7 ppm that comes from theNMR solvent. b) Draw the structure of the molecule and label each hydrogen with a letter(A, B, C...). Then fill in the peak assignment table below.  hydrogen chemical shift integration splitting pattern couples to

DEPT-135 DEPT - 90 DEPT - 45 T 200 CDS-03-521 180 4/5 160 140 - H₂CO T 120 75% + 100 ppm U 80 LL 60 40 20 0

Q8. How would you distinguish the following molecules using IR and Mass Spectrometry? Please label at least two differences for IR and two for MS. Please draw the mechanism for the formation of fragments which can distinguish the two molecules via mass spectrometry. HO

i) You did the following reaction, worked up in Ethyl Acetate and Water. NaBH 6=6 CH₂Cl₂ solvent Did your reaction work? What are the extra peaks in the NMR spectrum? 10 Chem Shift 1.27 2.03 2.35 3.65 4.15 4.61 5.28 7.11 7.25 9.54 Integral 0.036 0.035 1.53 0.50 OH 0.023 1.03 0.005 1.01 1.05 0.003 Multiplicity triplet singlet singlet singlet (removed by D20 shake) quartet singlet singlet doublet PPM doublet singlet

The three compounds hexane, 2-methylpentane, and 3-methylpentane correspond to the three mass spectra shown. Match each compound with the spectrum that best fits its structure on the basis of the fragmentation patterns. 100 MS Draw the structure corresponding to spectrum A. Select Draw Rings More Ful 50 C 0 20 40 60 100 A mlz 100 MS Lul 50- 0 0 20 40 60 B m/z 100 MS 50 d 0 20 40 60 80 100 m/z Draw the structure corresponding to spectrum B. Select Draw Rings More C Relative abundance ( 80 80 100 Erase Erase C Q2 Q Draw the structure corresponding to spectrum C. Select Draw Rings More C ✓ Erase

2. Draw the ¹H NMR spectrum of 1-Methoxyhexane and solve the structural formula. Then answer the following questions about your ¹H NMR spectrum of 1-Methoxyhexane. A. Handwritten illustration of the spectrum B. Analysis/ Interpretation a. How many types of H (signals)? b. What types of H (chemical shift)? c. How many H of each type are there (integration)? d. What are the connectivity (coupling patterns), show the solution? C. Solve the structural formula

Draw high resolution NMR spectra of the following compounds. Go to SDBS database and verify the spectra. Also, find IR spectra of each compound. 1. Ethanol 2. Acetic acid 3. Benzene 4. Ethyl acetate 5. Acetone 6. Diethyl ether 7. Dimethyl ether 8. Propanol- 9. Propanal

A student ran the reaction shown here separately using two different bases: once with NaOH and again with LDA. When NaOH was used, the organic product's UV-vis spectrum had a Amax of ~220 nm. When LDA was used, the product's spectrum had a max of -180 nm. In both cases, the formula of the organic product was C,H10. Explain. Br Base ? A