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Dr. Glaser's Visualization Center
To accompany Bruice, Organic Chemistry, 3/e, Chapter 11

Theme Molecule Name Chemical Formula
Thionyl Chloride Route to Alkyl Halides thionyl chloride (S) OSCl2
Thionyl Chloride Route to Alkyl Halides pyridine (S) C5H5N
Thionyl Chloride Route to Alkyl Halides pyridine, protonated (S) C5H5NH+
Structures of Sulfonyl Chlorides and Sulfonate Esters methanesulfonyl chloride (S) Me-SO2-Cl
Structures of Sulfonyl Chlorides and Sulfonate Esters methanesulfonate methylester (S) Me-SO2-OMe
Structures of Ethers "ether" (S) Et-O-Et
Structures of Ethers tetrahydrofuran (THF) (S) C4H8O
Structures of Ethers propylene oxide (S) C3H6O
Structures of Ethers benzene oxide (S) C6H6O
Structures of Thiol Derivatives methanethiol (S) Me-SH
Structures of Thiol Derivatives dimethylsulfide (S) Me-S-Me
Structures of Thiol Derivatives trimethylsulfonium cation (S) SMe3+
Structures of Benzene Derivatives chlorobenzene (S) C6H5Cl
Structures of Benzene Derivatives phenyllithium (S) C6H5Li

[a] All structures were optimized at the correlated level MP2(full)/6-31G*.