1. Organic Chemistry, 6th edition Paula Yurkanis Bruice
Chapter 14
NMR Spectroscopy
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

2. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
14.4
How many 1H NMR resonances would be expected for the following compound? 3 4 5 6 8
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

3. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
14.4
How many 1H NMR resonances would be expected for the following compound? 3 4 5 6 8
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

4. Which of the following protons gives a 1H NMR signal at 4.6 ppm?
14.7
Which of the following protons gives a 1H NMR signal at 4.6 ppm? 2 3 1 2 3 4 5 4 5 1
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

5. Which of the following protons gives a 1H NMR signal at 4.6 ppm?
14.7
Which of the following protons gives a 1H NMR signal at 4.6 ppm? 2 3
1 – 2.4 ppm
2 – 6.8 ppm
3 – 7.2 ppm
4 – 4.6 ppm
5 – 3.2 ppm 4 5 1
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

6. Predict the splitting pattern for:
14.10
Predict the splitting pattern for:
In order of protons a, b, c:
Doublet, doublet, singlet
Multiplet, triplet, singlet (the Cl splits “a”)
Triplet, multiplet, triplet
Triplet, triplet, singlet
All singlets (they are so similar)
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

7. Predict the splitting pattern for:
14.10
Predict the splitting pattern for:
In order of protons a, b, c:
Doublet, doublet, singlet
Multiplet, triplet, singlet (the Cl splits “a”)
Triplet, multiplet, triplet
Triplet, triplet, singlet
All singlets (they are so similar)
The N+1 rule is obeyed. No splitting is observed between protons “b” and “c”.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

8. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
14.10
Which of the following pure compounds would fit the splitting pattern and shift of the 1H NMR spectrum?
Br-CH2CH3
Cl-CH2CH2-Br
Br-CH(CH3)2
Cl2CHCH2-Br
HO-CH2CH3
water
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

9. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
14.10
Which of the following pure compounds would fit the splitting pattern and shift of the 1H NMR spectrum?
Br-CH2CH3
Cl-CH2CH2-Br
Br-CH(CH3)2
Cl2CHCH2-Br
HO-CH2CH3
Pure “E” would show additional splitting.
water
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

10. Which of the following compounds best fits the 1H NMR spectrum?
14.11
Which of the following compounds best fits the 1H NMR spectrum?
triplet
multiplet
quartet
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

11. Which of the following compounds best fits the 1H NMR spectrum?
14.11
Which of the following compounds best fits the 1H NMR spectrum?
Only “D” has the correct CH2 shift and integral ratios.
triplet
multiplet
quartet
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

12. How many 13C resonances are expected from this compound?
14.19
How many 13C resonances are expected from this compound? 5 7 8 10 11
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

13. How many 13C resonances are expected from this compound?
14.19
How many 13C resonances are expected from this compound? 1 4 5 7 8 10 11 3 1 2 5 6 4 5 7 8
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.