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Let's take another approach to that last reaction from the previous problem... Below is a similar reaction scheme, but this time, you are given the ¹H-NMR spectrum of the final product. If you interpret the spectrum correctly, then you should be able to identify the correct product from list below (enter your answer in the space provided only use the product number for your answer: 1, 2, 3, etc.). Then, answer any follow-up questions a. 6 2H 6 Br Product 1 t 5 5 Br Br Luxe Product 4 Product 2 4 S Product 3 3 PPM NBS light i. The 2 hydrogens (2H) at 5.7 ppm chemical shift represent those attached to what functional group? PPM 6H m 2 ii. The 3 hydrogens (3H) at 1.6 ppm chemical shift are split. What do we call this splitting pattern? iii. Which one of the products above matches the ¹H-NMR below (note: integration is not provide on purpose but you are given the splitting patterns) (Simply answer by entering the correct product number: 1, 2, 3, etc.)? 2 3H S Br Product 5 1 1 t 0 0

Let's take another approach to that last reaction from the previous problem... Below is a similar reaction scheme, but this time, you are given the ¹H-NMR spectrum of the final product. If you interpret the spectrum correctly, then you should be able to identify the correct product from list below (enter your answer in the space provided only use the product number for your answer: 1, 2, 3, etc.). Then, answer any follow-up questions a. 6 2H 6 Br Product 1 t 5 5 Br Br Luxe Product 4 Product 2 4 S Product 3 3 PPM NBS light i. The 2 hydrogens (2H) at 5.7 ppm chemical shift represent those attached to what functional group? PPM 6H m 2 ii. The 3 hydrogens (3H) at 1.6 ppm chemical shift are split. What do we call this splitting pattern? iii. Which one of the products above matches the ¹H-NMR below (note: integration is not provide on purpose but you are given the splitting patterns) (Simply answer by entering the correct product number: 1, 2, 3, etc.)? 2 3H S Br Product 5 1 1 t 0 0

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.1: Nuclear Magnetic Resonance Spectroscopy
Problem 2P
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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 11 10 R C=O ... OH R 'H 9 8 7 H ppm 6 OH C=C-H 5 NH H-C-X H-C-O -OH -NH X = F, Cl, Br (i.e. electronegative atom) 3 2 H-C-N H-C-S -CH3 -CH₂- C=C-H H-C-C=O -CH H-C-C=C HC-0 0 4000 DIO small range range of values broad peak =C-H N-H 3250- 3300 broad with spikes -3300 3500 -O-H broad-3300 -3400 O-H -CN usually strong N-H CO =C H H 2730- 2820 3000- 2 peaks 3100 1 H -C-H 2850- 2960 O 0 -C-O-H broad-3000 3000 -CEN 2200 -CICH ← 2200 2500 wavenumber, cm-1 2000 C H.C. N н 1680 0.00 0.00 0.00 H 1600- 1660 O C. OR 2 :ں 1600 1500 1000
Transcribed Image Text: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 11 10 R C=O ... OH R 'H 9 8 7 H ppm 6 OH C=C-H 5 NH H-C-X H-C-O -OH -NH X = F, Cl, Br (i.e. electronegative atom) 3 2 H-C-N H-C-S -CH3 -CH₂- C=C-H H-C-C=O -CH H-C-C=C HC-0 0 4000 DIO small range range of values broad peak =C-H N-H 3250- 3300 broad with spikes -3300 3500 -O-H broad-3300 -3400 O-H -CN usually strong N-H CO =C H H 2730- 2820 3000- 2 peaks 3100 1 H -C-H 2850- 2960 O 0 -C-O-H broad-3000 3000 -CEN 2200 -CICH ← 2200 2500 wavenumber, cm-1 2000 C H.C. N н 1680 0.00 0.00 0.00 H 1600- 1660 O C. OR 2 :ں 1600 1500 1000
a. Let's take another approach to that last reaction from the previous problem... Below is a similar reaction scheme, but this time, you are given the ¹H-NMR spectrum of the final product. If you interpret the spectrum correctly, then you should be able to identify the correct product from list below (enter your answer in the space provided - only use the product number for your answer: 1, 2, 3, etc.). Then, answer any follow-up questions 6 2H 6 NBS light Milline Br butter Product 3 Br Product 1 t 5 5 Product 2 4 S 3 PPM 4 Br Product 4 3 PPM i. The 2 hydrogens (2H) at 5.7 ppm chemical shift represent those attached to what functional group? 6H ii. The 3 hydrogens (3H) at 1.6 ppm chemical shift are split. What do we call this splitting pattern? iii. Which one of the products above matches the ¹H-NMR below (note: integration is not provide on purpose but you are given the splitting patterns) (Simply answer by entering the correct product number: 1, 2, 3, etc.)? 3 2 2 3H S Br Product 5 1 1 t 0 0
Transcribed Image Text:a. Let's take another approach to that last reaction from the previous problem... Below is a similar reaction scheme, but this time, you are given the ¹H-NMR spectrum of the final product. If you interpret the spectrum correctly, then you should be able to identify the correct product from list below (enter your answer in the space provided - only use the product number for your answer: 1, 2, 3, etc.). Then, answer any follow-up questions 6 2H 6 NBS light Milline Br butter Product 3 Br Product 1 t 5 5 Product 2 4 S 3 PPM 4 Br Product 4 3 PPM i. The 2 hydrogens (2H) at 5.7 ppm chemical shift represent those attached to what functional group? 6H ii. The 3 hydrogens (3H) at 1.6 ppm chemical shift are split. What do we call this splitting pattern? iii. Which one of the products above matches the ¹H-NMR below (note: integration is not provide on purpose but you are given the splitting patterns) (Simply answer by entering the correct product number: 1, 2, 3, etc.)? 3 2 2 3H S Br Product 5 1 1 t 0 0
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