Question

What happens to cyclohexene when reacted with 1) PhCOOOH 2) EtLi, then H3O 3) PCC

Answer 1

can i help

Answer 2

@jlmurden

Answer 3

I'm pretty sure that the first step involves formation of an epoxide.

Answer 4

lithium reagents would probably add into our epoxide like this.

this is just one of those things where carbon is actually the more electronegative element so the negative charge will be on carbon, not lithium. this is a great way our carbon can add to our epoxide which is highly reactive.



take a look carbon actually dumps its electrons onto oxygen and we're left with an oxygen anion like this.



the acid in the second step is called a work up/ quench to make sure our reaction has gone to completion.

The result here is an alcohol.



PCC is a mild oxidant, you use it if you want to reduce primary/secondary alcohols down to aldehydes or ketones.

secondary alcohols become ketones, primary alcohols become aldehydes with PCC.

of course aldehydes would be more reactive because the carbonyl C=O is more available for attack by a nucleophile.