Organic Chemistry

574 CHAPTER 14 NMR Spectroscopy

Problems

41. How many signals are produced by each of the following compounds in its

a. NMR spectrum? b. NMR spectrum?

1. 
   
   
   
   3. 
      
      
      
      5. 
         
      
      
      
      
   
   
   
   


2. 
   
   
   
   4. 
      
      
      
      6. 
         
      
      
      
      
   
   
   
   


3. Draw a splitting diagram for the proton and indicate its multiplicity if

a. b.

43. Label each set of chemically equivalent protons, using afor the set that will be at the lowest frequency (farthest upfield) in
    the NMR spectrum,bfor the next, etc. Indicate the multiplicity of each signal.

a. c. e.

b. d. f.

44. Match each of the NMR spectra on page 575 with one of the following compounds:

CH 3 CH 2 CCH 2 CH 3

O

CH 3 CH 2 CCH 3

O

CH 3 CNO 2

CH 3

CH 3

CH 3 CH 2 CH 2 NO 2 CH 3 CH 2 NO 2 CH 3 CHBr

CH 3

1 H

CH 3 CH 2 CH 2 CCH 2 Cl ClCH 2 CH 2 CH 2 CH 2 CH 2 Cl

O

CH 3 CH 2 CH 2 OCH 3

ClCH 2 CCHCl 2

CH 3

CH 3

CH 3 CHCCH 2 CH 2 CH 3

CH 3

O

CH 3 CHNO 2

CH 3

1 H

Ha CCCX

Ha

Ha Hb Hc

XX

Jba=Jbc Jba= 2 Jbc

Hb

O

C

O

OCH 2 CH 3

Cl

O

O

CH 3 OCHCH 3

CH 3

1 H 13 C