which electrophilic substittuion reaction is reversible

[jd399]

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1.sulfonation
2.oxidation
3.halogenation
4.acylation
5.hydrogenation

This is from Destroyer #96 orgo.
Please explain ur answer =)

thank u!

 

[dentista123]

sulfonation---addition of SO3H with an acid. I memorized this in OChem II. As for an explanation...well, I can help you out with how I think of it. Not sure how accurate my thoughts are. I think of a tosylate. It's a really good leaving group. All those all those oxygens to stabilize the charge.

 

[pbure9]

sulfonation---addition of SO3H with an acid. I memorized this in OChem II. As for an explanation...well, I can help you out with how I think of it. Not sure how accurate my thoughts are. I think of a tosylate. It's a really good leaving group. All those all those oxygens to stabilize the charge.

Yup all you need to reverse sulfonation is add H+/H2O

 

[jd399]

how does water reverse it?

 

[ethanyoo726]

Here is how water reverses it...

http://web.centre.edu/muzyka/organic/syllabi_tests/sulfonationMech.gif

 

[pbure9]

lol.. ye that explains it... basically what dentista said. It's pretty stable on its own