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Chem 210-1 F07 Ex2 p06c

Chem 210-1 F07 Ex2 p06c - another...

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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
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Unformatted text preview: another product, "W". "W" has the formula C 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)...
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