Epoxide

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SodiumChanel

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10+ Year Member
If I have an epoxide (cyclohexane with no extra substituent) and the reagents are NaOH/H20 - does that produce OH and a ONa substitudent on each side or both OH on each side but in anti addition?

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SodiumChanel said:
If I have an epoxide (cyclohexane with no extra substituent) and the reagents are NaOH/H20 - does that produce OH and a ONa substitudent on each side or both OH on each side but in anti addition?

😕😕😕😕😕😕
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The latter. After the opening the O- will rip away an H from the H2O. (Remember that the NaOH completely disassociates into Na+ and OH-)
 
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SodiumChanel said:
so the answer is a cyclohexane with two substituents:
1) OH from the O from epoxide with H from the water
2) OH from NaOH?
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Precisely.

And just for the hell of it....if it was a syntheses problem starting from a cyclohexene it would be:

1. MCPBA
----------------->
2.NaOH/H2O
 
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