Question

NEED HELP WITH B) C) D) E) F) and G) that apply to the spectra below.

OTHER ANSWERS ARE THERE TO SUPPLEMENT

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1400 - 1200- -11.40 D 1000 - 800 Response - MiVolts -12.07 W Height: 72 mm Width: 9 mm 800 T T Height: 125 mm Width: 8 mm 400

5. Using the GC mentioned in question 4 and the values listed on the chromatogram for the height and width (at half height) of each peak, calculate the percent composition for each product (A, B and C). Be sure to show your work.

Area of peak A = 125 x 8 = 1000mm2

Area of peak B = 72 x 9 = 648mm2

Area of peak C = 10 x 6 = 60mm2

Total peak area = 1708mm2

Percent composition of A = (1000/1708) x 100% = 58.5%

Percent composition of B = (648/1708) x 100% = 37.9%

Percent composition of C = (60/1708) x 100% = 3.5 %

6. The products corresponding to each peak on the GC are the ortho, meta, and para isomers of the nitrated product shown in the scheme for reaction 1. These isomers were isolated, and a proton NMR was taken for each.

a) Fill in the table below to assign each isomer (ortho, meta, para) to its proton NMR.

Spectrum For Peak A on GC For Peak B on GC For Peak Con GC Isomer Ortho Nitro Toluene Para Nitro Toluene Meta Nitro Toluene

b) Which area of the spectrum did you focus on and which key piece of information (chemical shift, integration, or splitting pattern) helped you decide which spectrum belonged to which isomer? Please explain your responses. Please explain the following chemical shifts below with integration and splitting pattern and explanation for each (if they're correct).

c) Using your answers to question 5 and 6a, what percent of the mixture obtained in reaction 1 is the ortho isomer?

d) What percent of the mixture obtained in reaction 1 is the meta isomer?

e) What percent of the mixture obtained in reaction 1 is the para isomer?

f) Could we have used Mass Spectrometry after the GC analysis (GC-MS) to identify which peak on the GC was which isomer? Why or why not?

g) Could we have used IR to differentiate between the ortho, meta, and para isomers? Why or why not?

Peak A

Proton NMR Spectrum for Peak A on Gas Chromatogram: ЗН 1H 2H 1H 9 8 7 6 5 3 2 0 PPM Expansion of downfield signals: 1H 2H 1H

7.3 ppm Ha 2.5 ppm CH3 7.5 ppm Hb 7.5 ppm Hc Hd 7.9 ppm

Peak B

Proton NMR Spectrum for Peak B on Gas Chromatogram: ЗН 2H 2H 9 8 5 3 0 PPM Downfield signals are both doublets.

7.5 ppm Ha 8.2 ppm 2.3 ppm H3C. Hb O 7.5 ppm Ha Hb 8.2 ppm

Peak C

Proton NMR Spectrum for Peak Con Gas Chromatogram: 3H 2H 1H 1H 9 8 7 6 3 2 0 PPM Expansion of downfield signals: 2H 1H 1H ted

2.3 ppm CH3 7.5 ppm 8.05 ppm Hd. Ha 0 7.45 ppm Hc Hb 8.1 ppm

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