Question
D-Arabinose, can someone please analyze its Carbon and Proton NMR?

abundance 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 20.0 70.650 2170.507 170.135 169.878 77.299 770
abundance ........20...3.0...40...50... ...6.0 . 7.0 8.0 2.132 2005 2070 - 2014 2.046 15.02
0 0
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Answer #1

CHOM HO H Hah Hstructure of D-arabinose clearly says it all . The C1 which is directly attached to oxygen by double bond is very much dishielded and gives a shift near 170 ppm , the carbon next to carbonyl carbon is also deshielded but not as much as carbonyl carbon remaining carbons comes under 50 ppm bonded to other carbons and deshielding decreases as distance decreases .

Similarly in H NMR the aldehyde proton is very much deshielded due to electron withdrawing property of carbonyl group . The next desheilded proton is the alpha proton which will give doublet . Hydrogen bonded to C3 will show double doublet and shift will be less than alpha proton . The hydrogen bonded to remaining carbon will show decrease in chemical shift with their corresponding coupling according to the number of neighboring hydrogen atom near 2 ppm . The OH protons resonate at different frequency above 5 ppm

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