Lewis structure dimethyl sulfoxide

Polar structures must be used for compounds containing an atom in a higher valence state, such as sulfur or phosphorus. Thus, if we treat sulfur in dimethyl sulfoxide (DMSO) formally as a divalent atom, the calculated index, 0, is compatible with the structure in Figure 1.12. We must use only formulas with filled valence shells that is, the Lewis octet rule must be obeyed. 

Example 1.5. Write two possible Lewis structures for dimethyl sulfoxide, (CHj)2SO, and calculate formal charges for all atoms in each structure. 

A formal total synthesis of ( )-morphine has been achieved by adopting the above synthetic route (Scheme 18). The tetrahydropyridine 91, prepared from the reaction of A/ -methyl-4-piperidone with 2,3-dimethoxy-phenyllithium, followed by dehydration, was converted to the bicyclic en-amine 92 by treatment with the ylic dibromide. Kinetic protonation of 92 with perchloric acid gave the trans-fused immonium salt, which upon dissolution in methanol equilibrated to the thermodynamically prefered cis isomer 93. Treatment of 93 with diazomethane brought about the formation of the aziridinium salt 94, which was readily transformed into the a-amino aldehyde 95 by its oxidation with dimethyl sulfoxide. It is also worth noting that the Komblum oxidation of aziridinium salts leads to the construction of a-amino aldehydes efficiently. Lewis-acid-catalyzed cyclization of 95 afforded the morphinan carbinol 96 in 80% yield. Successive mesylation and reduction of the mesylate derived from 96 with LiBEtjH afforded morphinan (97) in excellent yield. In this instance, direct conversion of 93 to 97 by treatment with diazomethane gave approximately 1 % of the desired product. Lemieux-Johnson oxidation of 97 under acidic conditions furnished the ketone 98, which was previously transformed into ( )-morphine by Gates. In order to confirm the structure of 98, its conversion to the known... 

Dimethyl sulfoxide (DMSO) has been used as an anti-inflammatory mb for racehorses. DMSO and acetone seem to have similar structures, but the C=0 carbon atom in acetone is planar, while the S=0 sulfur atom in DMSO is pyramidal. Draw correct Lewis structures for DMSO and acetone, predict the hybridizations, and explain these observations. 

Write a Lewis structure and determine the molecular geometry of dimethyl-sulfoxide (DMSO), (0113)280. Draw a sketch of DMSO acting as a ligand in the NAMI anticancer complex. 

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