chemists - help a brotha out

[lI1|1!]

6 12 6

[catbirdseat]

So I have this take home quiz...and this one problem I'm not quite sure of. I think the answer is a, but who knows. Originally I thought it was E, however she changed the answers and added an extra carbon to that answer. Any help?

 

It would appear that in this case, two equivalents of Grignard reagent will add across the carbonyl bond. Thus, either A or E might be the answer. The only question being, whether the oxygen resulting from the opening up of the lactone ester bond is methylated or not. I have to think about this some more.

[archenemy]

Dude, you totally cheated and looked at my answer.

[ClimbingPanther]

i've never heard them called "answers" before

[archenemy]

solution?

[archenemy]

doodle?

[tvashtarkatena]

zeelution.

[JayB]

So I have this take home quiz...and this one problem I'm not quite sure of. I think the answer is a, but who knows. Originally I thought it was E, however she changed the answers and added an extra carbon to that answer. Any help?

 

It would appear that in this case, two equivalents of Grignard reagent will add across the carbonyl bond. Thus, either A or E might be the answer. The only question being, whether the oxygen resulting from the opening up of the lactone ester bond is methylated or not. I have to think about this some more.

 

Cool. My first guess was A. Figured the CH3 would wage a nucleophillic attack the carbonyl group and make something that looked like A, but it's been ~14 years since Ochem, so it's all going fuzzy and something tells me I'd get about 25% of the answers right on a multiple choice test with four potential answers for each question...

[Lionel_Hutz]

oops, now everyone knows I'm sasquatch. secret's out.

 

I'da pegged you for a jackalope.

 

You want to peg climbing panther? In exhcange for a jackelope? Take it to the sex thread, you pervs. . .

Edited February 15, 2008 by Lionel_Hutz

[kevino]

Since posting it I concluded it was A because its in a solution of strong acid, H3O. And since the O has a partial negative and the h30 is + it would easily give up a proton, in this case H to make the primary alcohol.

[Mal_Con]

Whoa, it has been a while never used grignard reagents much. Mostly concerned with indol derivatives an such. We would take an nmr and see which groups popped up. Predictions often go awry.

[Choada_Boy]

Since posting it I concluded it was A because its in a solution of strong acid, H3O. And since the O has a partial negative and the h30 is + it would easily give up a proton, in this case H to make the primary alcohol.

 

It seems you've discovered the concept of the Bronsted-Lowry acid, young Padawan.