In the reaction between NaOH and citric acid , the OH on the second carbon doesn't react. Why? Only the three OH's in the carboxyl group react. Why doesn't the OH attached to 2nd carbon react?? If possible, explain with mechanism too...thanks a lot!!

Question

abb0t · Answer

can you sow me the mechanism that shows where you're confused?

anonymous · Answer

In this document, the reaction is given. My doubt is, why doesn't the OH of second carbon react?

abb0t · Answer

There's only one hydroxyl group in citric acid. And, alcohols are NOT good leaving groups, especially when treated with base.