Epoxide

[SodiumChanel]

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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?

😕😕😕😕😕😕

 

[Moka11]

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?

😕😕😕😕😕😕

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-)

 

[SodiumChanel]

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-)

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?

 

[Moka11]

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?

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

 

[SodiumChanel]

Precisely.

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

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

awesome. thumbs up for you. Thanks so much. Hope you get 25+ on your orgo! 😀