Chem210-1 F07 Ex2 p06ca

Chem210-1 F07 Ex2 p06ca - 6 H 10 S - the infrared spectrum...

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6. Compound "X" shown on the right is 4-bromocyclohexanethiol: SH Br Reaction of cis -4-bromocyclohexanethiol with sodium hydroxide (NaOH) in aqueous ethanol gives as one product the compound "Y", which has formula C 6 H 12 OS. The same reaction with the trans -isomer of "X" yields as one product "Z", which also has formula C 6 H 12 OS. Both "Y" and "Z" exhibit prominent peaks at about 3300 cm -1 in the IR "X" In addition, one (and only one) of the isomeric forms of "X" gives a significant amount of another product, "W". "W" has the formula C
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Unformatted text preview: 6 H 10 S - the infrared spectrum of "W" indicates that it does NOT possess an alkene double bond. a) Provide below clear, unambiguous structures for "Y", "Z", and "W" (3 points each) b) Identify which isomer of "X" (the cis or the trans ) gives rise to the formation of "W", AND provide a step-by-step mechanism for that transformation (6 points) H SH HO H H SH H OH "Y" "Z" H H S "W" trans H S Br H "Y" H O-H H S Br H "Y" H Br S H H S "W"...
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This note was uploaded on 02/28/2012 for the course CHEM 210-1 taught by Professor Trzupek during the Fall '08 term at Northwestern.

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