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O H3 C CH3
CH3 CCH3 ClCH2 CH2 Cl C C
H3 C CH3
Propanone 1,2-Dichloro- Cyclopentane 2,3-Dimethyl-
(Acetone) ethane 2-butene
Equivalent Hydrogens
A molecule with 2 or more sets of
equivalent hydrogens gives a different
NMR signal for each set.
Cl Cl CH3
CH3 CHCl O C C
H H
1,1-Dichloro- Cyclopent- (Z)-1-Chloro- Cyclohexene
ethane anone propene (3 signals)
(2 signals) (2 signals) (3 signals)
Chemical Equivalence
How many signals in 1H NMR spectrum?
CH3
1 3 5 4
2
O
O O
O
4
6
1
H NMR CHEMICAL SHIFT RANGES
valence electrons
shield the nucleus
from the full effect
of the applied field
Aromatic Protons, = 7- 8
shield
ed
deshield
ed
ANISOTROPIC FIELD IN AN ALKENE
The double bond is oriented perpendicular to the
external field with electrons likewise circulating 4.5-6.5
at right angles
protons are
Deshielded deshielded
fields add
H H shifted
downfield
C=C
H H
secondary
magnetic
(anisotropic)
Bo field lines
ANISOTROPIC FIELD IN AN ALKYNE
For alkynes the most effective orientation is the external field in
parallel with electrons circulation around the triple bond
1.5 3.5
secondary
magnetic
Shielded hydrogens
(anisotropic)
fields subtract are shielded
field
Aldehyde Proton, 9-10
Electronegative
oxygen atom
The fine structure
The splitting of the groups of resonances into
individual lines is called fine structure.
Relative areas of signals are proportional to the
number of H giving rise to each signal,
(n+1) Rule
Signal Splitting: Spin-Spin Coupling
The signal from a given proton will be split by the
effect of magnetic fields associated with protons on
adjacent carbons
Characteristic peak patterns result from signal splitting
that are related to the number of protons on adjacent
carbons
Signal splitting is not observed between homotopic or
enantiotopic protons
Signal Splitting: Spin-Spin Coupling
The effect of signal splitting is greatest between atoms
separated by 3 or fewer bonds
Signal splitting occurs only when two sets of protons
have different chemical shifts (i.e., are not chemical
shift equivalent)
Two singlet
signals
Signal Splitting: Spin-Spin Coupling
Bo
downfield upfield
neighbour aligned neighbour opposed
At any given time about half of the molecules in solution will
have spin +1/2 and the other half will have spin -1/2.
SPIN ARRANGEMENTS
One neighbour One neighbour
n+1 = 2 n+1 = 2
doublet doublet
H H H H
C C C C