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Diastereotopic Hydrogens are Not Chemically Equivalent

We can conclude that when two different sets of protons split a signal, the multiplicity of the signal can be determined by using [Pg.681]

Enantiotopic hydrogens show one NMR signal because they are chemically equivalent. [Pg.681]

Enantiotopic hydrogens are chemically equivalent, so they show only one NMR signal. [Pg.681]

The carbon to which the enantiotopic hydrogens are attached is called a prochlral carbon. If Hq is replaced by a deuterium, the asymmetric center will have the R configuration. Thus, H is called the pro-R-hydrogen. Similarly, H is called the pro-S-hydr en because replacing it with a deuterium would generate an asymmetric center with the S configuration. [Pg.681]

If a carbon is bonded to two hydrogens in a compound that has an asymmetric center, then the two hydrogens are called diastereotopic hydrogens, because replacing each of them in turn with deuterium (or another group) creates a pair of diastereomers. [Pg.681]


We know that diastereotopic hydrogens are not chemically equivalent because they do not react at the same rate with achiral reagents. For example, removal of H and Br to form ( )-2-butene occurs more rapidly than removal of Ha and Br to form (Z)-2-butene because ( )-2-butene is more stable than (Z)-2-butene (Section 10.6). Because diastereotopic hydrogens are not equivalent, the W + 1 rule has to be applied to them separately. [Pg.682]


See other pages where Diastereotopic Hydrogens are Not Chemically Equivalent is mentioned: [Pg.681]    [Pg.681]   


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