Organic Chemistry, 6th edition Paula Yurkanis Bruice

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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.