DAT Destroyer Orgo #19

[mkhan27]

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Question asks: "Glucose can isomerize into fructose when put in base. Which of the below structures represent an intermediate seen during this conversion?" Below is the question and the answer with an explanation. I get what they did with the mechanism and conversion, but my question is if they literally want us to know exact step-by-step mechanism/conversions of reactions for Orgo on the DAT? Thanks in advance everyone!

 

[emminent]

No don't have to worry about mechanisms too much especially not step by step. However chad did say they would throw in very simple mechanisms like asking imitation step for NBS which is Br breaking off of the NBS structure.

So again don't worry about mechanisms but if there is it's pretty simple.

 

[TheEpicFruitCake]

Well, tbh you should probably be able to "guess" the intermediate as the others don't make sense at all. If you didn't know what fructose looked like you're SOL though

A is just no... Base making something positively charged wtf?
B is plausible even if you had no idea what was happening
C is reacting on the wrong end
Eh... D doesn't make much sense but this would be the only other possibility, still not likely
E is fructose, so not an intermediate