First Name Last Name NMR IR Tutorial Report Sheet PDF

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CHEM 2120 W21

Part 1: NMR – Chemical Shifts and Equivalent C/H Determine how many different signals will be observed in the 1H-NMR and 13C-NMR for each of the following compounds (identify and indicate which nuclei are equivalent and which are not). [10 marks] Use the drop down menus to answer this question. Below is a sample of how you should answer the question. Sample molecule: CH3CH2CH3 Number of 13C NMR peaks: Number of 1H NMR peaks: Molecular Component Equivalent Nuclei in 13C NMR Equivalent Nuclei in 1H NMR

CH3

CH2

CH3

CH3

CH2

OH

a) CH3CH2OH Number of 13C NMR peaks: Number of 1H NMR peaks: Molecular Component Equivalent Nuclei in 13C NMR Equivalent Nuclei in 1H NMR b) CH3CH2CH2CH2CH2CH3 Number of 13C NMR peaks: Number of 1H NMR peaks: Molecular Component Equivalent Nuclei in 13C NMR Equivalent Nuclei in 1H NMR

CH3

c) 2,2-dimethylpropane 1 4 2 3 Number of 13C NMR peaks: Number of 1H NMR peaks:

CH2

CH2

CH2

CH2

CH3

CHEM 2120 W21

Molecular Component Equivalent Nuclei in 13C NMR

CH3 (1)

CH3(2)

CH3(4)

CH3(3)

C

Equivalent Nuclei in 13C NMR d) 2-methyl-1,3,5-trinitrobenzene (TNT)

2

3

1

4 6

5

Number of 13C NMR peaks: Number of 1H NMR peaks: Molecular Component Equivalent Nuclei in 13C NMR

CH3

C (1)

C (2)

CH2 (3)

C (4)

CH3 (5)

C (6)

Equivalent Nuclei in 1H NMR e) 1,4-dichloro-2,5-diethyl-benzene 1

2 3

4 5

10

6

7 8

9 Number of 13C NMR peaks: Number of 1H NMR peaks: Molecular Component Equivalent Nuclei in 13C NMR Equivalent Nuclei in 1H NMR

CH3 (1)

CH2 (2)

C (3)

CH2 (4)

C (5)

C (6)

CH2 (7)

CH3 (8)

CH2 (9)

C (10)

CHEM 2120 W21

Part 2: NMR – Splitting and Integration Match the three NMR spectra (1H-NMR on bottom and 13C-NMR on top) supplied by your instructor with the three compounds listed below and explain your reasoning, i.e. why the spectrum fits the molecule chosen and not the others (consider both the number of signals and the coupling patterns). [7 Marks]

2-methyl-3-hexanone The spectra set that corresponds to this molecule is: Explanation:

CHEM 2120 W21

2, 4-dimethyl-3-pentanone The spectra set that corresponds to this molecule is: Explanation:

CHEM 2120 W21

4, 4-dimethyl-2-pentanone The spectra set that corresponds to this molecule is: Explanation:

CHEM 2120 W21

Part 3: IR Match the four IR spectra supplied by your instructor with the four compounds listed below and explain your reasoning, i.e. why the spectrum fits the molecule chosen and not the others. [8 Marks]

The spectra that corresponds to this molecule is: Explanation:

Phenacetin

The spectra that corresponds to this molecule is: Explanation:

menthol

The spectra that corresponds to this molecule is: Explanation:

CHEM 2120 W21

para-methoxyphenol

The spectra that corresponds to this molecule is: Explanation:

2,4-dimethyl-3-pentanone...