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NMR data Summary NMR solvent: DMSO-d6 'H NMR: Spliting (Multiplicity) Chemical Shift Integration 1H 1H 9.67 singlet singlet doublet doublet singlet 9.17 7.37 2H 6.72 2.00 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 1 "N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the 'H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the HN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'HISN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 1"C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of the carbon of the methyl group. Step 5: Look at the 'H"C HSQC spectrum - Use this spectrum to assign the chemical shifts of the aromatic carbon atoms that are bound to a proton; confirm your assignment of the methyl carbon. Make a note concerning the carbon atoms that are not bound to a hydrogen atom. Step 6: Look at the 'HC HMBC spectrum - assign the chemical shifts of the aromatic carbon atoms that are not bound to a proton.

NMR data Summary NMR solvent: DMSO-d6 'H NMR: Spliting (Multiplicity) Chemical Shift Integration 1H 1H 9.67 singlet singlet doublet doublet singlet 9.17 7.37 2H 6.72 2.00 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 1 "N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the 'H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the HN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'HISN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 1"C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of the carbon of the methyl group. Step 5: Look at the 'H"C HSQC spectrum - Use this spectrum to assign the chemical shifts of the aromatic carbon atoms that are bound to a proton; confirm your assignment of the methyl carbon. Make a note concerning the carbon atoms that are not bound to a hydrogen atom. Step 6: Look at the 'HC HMBC spectrum - assign the chemical shifts of the aromatic carbon atoms that are not bound to a proton.

Principles of Instrumental Analysis
Principles of Instrumental Analysis
7th Edition
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Chapter19: Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
Problem 19.23QAP
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NMR data Summary NMR solvent: DMSO-d6 'H NMR: Splitting (Multiplicity) Integration Chemical Shift 9.67 singlet 1H singlet doublet 9.17 7.37 6.72 2.00 1H 2H doublet singlet 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 15N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the 'HSN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'H1SN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 13C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of the carbon of the methyl group. Step 5: Look at the 'H13C HSQC spectrum - Use this spectrum to assign the chemical shifts of the aromatic carbon atoms that are bound to a proton; confirm your assignment of the methyl carbon. Make a note concerning the carbon atoms that are not bound to a hydrogen atom. Step 6: Look at the H®C HMBC spectrum – assign the chemical shifts of the aromatic carbon atoms that are not bound to a proton.
Transcribed Image Text:NMR data Summary NMR solvent: DMSO-d6 'H NMR: Splitting (Multiplicity) Integration Chemical Shift 9.67 singlet 1H singlet doublet 9.17 7.37 6.72 2.00 1H 2H doublet singlet 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 15N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the 'HSN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'H1SN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 13C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of the carbon of the methyl group. Step 5: Look at the 'H13C HSQC spectrum - Use this spectrum to assign the chemical shifts of the aromatic carbon atoms that are bound to a proton; confirm your assignment of the methyl carbon. Make a note concerning the carbon atoms that are not bound to a hydrogen atom. Step 6: Look at the H®C HMBC spectrum – assign the chemical shifts of the aromatic carbon atoms that are not bound to a proton.
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