http://i32.photobucket.com/albums/d5/stewartJames/ochem.jpg

Is this wrong? The second step in particular.

I might be just tired, but I'm sick of wondering....

Ignoring the fact that it's not clear if it's done in acid or base (if it were in acid, there would be a protonation step; if it were base, the ethanol would've been de-protonated), it looks fine to me. LiAlH4 reduces aldehydes, ketones, and carboxylic acids to alcohol (NaBH4 reduces only aldehydes and ketones to alcohols). Sorry if you already knew that; that last sentence was more for my own review :).

I thought...I am not sure, but I thought that LAH will cleave esters...anyone else? which means that the 2nd step might be wrong. where did this come from?

wow nice to see i am not the only one having problems with this one,

here you go,

http://forums.studentdoctor.net/showthread.php?t=432583

that's the best explanation i found so far, and i went with it, anyone else with better explanation help us out, thanks

wow nice to see i am not the only one having problems with this one,

here you go,

http://forums.studentdoctor.net/showthread.php?t=432583

that's the best explanation i found so far, and i went with it, anyone else with better explanation help us out, thanks

Yeah, that double bond is the only thing I could think of why it is different.

Normally LiAlH4 will take ester to two alcohols and carboxylic acid to alcohol, not a geminal diol

Thanks

I thought...I am not sure, but I thought that LAH will cleave esters...anyone else? which means that the 2nd step might be wrong. where did this come from?

Agreed. Kappy Subject Test 5. Problem #6

Ahh Kaplan...:) Thanks for letting us know tRNA. That makes sense about the double bond, lets just hope I would recognize that on the actual test!