H NMR Problems: - How Many Unique Proton Environments Are There in

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H NMR Problems
• How many unique proton environments are there in:

CH3CH2Br CH3CH2Br 2 environments

CH3 CH3
CH3OCH2CH2CHCH3 CH3OCH2CH2CHCH3 5 environments

CH3 CH3 CH3


H C H
C C
4 environments
C C
H C H
H
H NMR Problems
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CH3 CH3 CH3 CH3


C C C C
CH3 H CH3 H

4 environments

CH3CH2 CH2CH3 CH3CH2 CH2CH3


C C C C
H H H H

3 environments

Symmetry Simplifies Spectra!!!


O
CH3CCH3
OCH3 CH3

O
CH3COCH3
1
H NMR Problems
• Predict the splitting patterns (multiplets) for each proton
environment in the following:
singlet

singlet
CH3CHBr2
doublet

doublet

CH3OCH2CH2Br triplet

triplet

triplet
ClCH2CH2CH2Cl
triplet

quartet
O CH3 quartet
CH3CH2COCHCH3
quintet

septet
CH3

CH3
O
CH3COCH2CH3 OCH2

CH3
(2H) (3H) (3H)
CH3

OCH2
CH3 CH3

O
OCH2 CH2
CH3CH2COCH2CH3

CH3 CH3

OCH2 CH2
.
ethyl C6H12O2
butanoate

O CH3 CH3

CH3CH2CH2COCH2CH3

CH2
OCH2

CH2
CH3

CH3

O
CH3CCH2CH3 CH2

CH3

CH3

CH2
CH3

H H
O
H
H
CH3C H

H
H H

CH3

H
C H
C C
H H C C
H C H
H
H
CH3
CH3CH2CH2OH

CH2

CH2 O
OH

CH3

CH2

CH2 O
OH
CH3

CH2
CH3CH2CH2CH2OH CH2 O
CH2

OH

CH3

CH2 O CH2
CH2
OH
CH2
and CH3
CH2
CH3CH2CH2CH2CH2OH CH2 O

CH2

OH

CH2 CH3
and
CH2
CH2 O

CH2
OH
CH3

CH3
H
H
H
H
H
H H H other Hs

CH3

HH other Hs
H
CH3

CH2
CH3CH2CH2Br
CH2

CH3

CH2

CH2
H2C=C=CHCH2CH2OH
CO2H
H3C O
N CCH3
H 3C
O
H3C NHCCH3
C C

HC H
O

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