We are talking about the difference between the structures of borneol and isoborneol (see the structures of both compounds in the link referenced below). Both are bicyclic molecules with the norbornane structure at their cores. The gem dimethyl group in question is the carbon at the top of the structures with two methyl (CH3) groups attached to it. The only difference between the two molecules is the spatial orientation of the hydroxyl (OH) group. In borneol, the hydroxyl group is pointed down and away from the gem dimethyl group. In isoborneol, the hydroxyl group is pointed up and toward the gem dimethyl group. Since NMR distinguishes between chemically unique hydrogen atoms, the hydroxyl group in isoborneol affects the methyl group that is pointed toward it but not the methyl group pointed away from it, thus the two methyl groups appear as two different peaks in the NMR spectrum. In the case of borneol, the hydroxyl group is pointed in the opposite direction and therefore exerts essentially no effect on the gem dimethyl group, thus it appears as a single peak in the NMR spectrum.
https://en.wikipedia.org/wiki/Borneol
Friday, November 10, 2017
Explain why the gem-dimethyl groups appear as separate peaks in the proton NMR spectrum of isoborneol although they almost overlap in borneol.
Subscribe to:
Post Comments (Atom)
Why is the fact that the Americans are helping the Russians important?
In the late author Tom Clancy’s first novel, The Hunt for Red October, the assistance rendered to the Russians by the United States is impor...
-
There are a plethora of rules that Jonas and the other citizens must follow. Again, page numbers will vary given the edition of the book tha...
-
The poem contrasts the nighttime, imaginative world of a child with his daytime, prosaic world. In the first stanza, the child, on going to ...
-
The given two points of the exponential function are (2,24) and (3,144). To determine the exponential function y=ab^x plug-in the given x an...
-
The play Duchess of Malfi is named after the character and real life historical tragic figure of Duchess of Malfi who was the regent of the ...
-
The only example of simile in "The Lottery"—and a particularly weak one at that—is when Mrs. Hutchinson taps Mrs. Delacroix on the...
-
Hello! This expression is already a sum of two numbers, sin(32) and sin(54). Probably you want or express it as a product, or as an expressi...
-
Macbeth is reflecting on the Weird Sisters' prophecy and its astonishing accuracy. The witches were totally correct in predicting that M...
No comments:
Post a Comment