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Unformatted text preview: 2 CH 3 NBS, CCl 4 1 CH 2 CH 3 4 CH 2 CH 3 5 Br Br 2 3 3. (12 points) The reaction of methyl bromide with hydroxide ion produces methanol through an S N 2 mechanism. Draw the structure of the transition state. Is the reaction faster in the solvent of H 2 O or DMSO (dimethyl sulfoxide) ? Draw an energy diagram for the reaction in both solvents to rationalize your answer. 5. (12 points) The tosylate (OTos, a good leaving group) of ( 2R , 3S )-3-phenyl-2-butanol undergoes E2 elimination on treatment with sodium ethoxide (Na + -OCH 2 CH 3 ) to yield an alkene. Draw structures of the tosylate (in Newman projection), the transition state of the reaction, and the product. Please show stereochemistry where appropriate. CHCHCH 3 H 3 C OTos Na +-OCH 2 CH 3 Alkene...
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This note was uploaded on 02/27/2010 for the course CHEM CHEM111 taught by Professor Dai during the Fall '06 term at HKUST.
- Fall '06
- Organic chemistry