Orgoman ch9 Q12

[babowc]

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Can someone explain how A results in the product?
I'm not seeing where the extra CH3 attached to the C attached to OH comes from..

Thanks in advance guys!

 

[KyoPhan]

In this case with an ester, it'll add the grignard twice.

For the step by step mechanism: Scroll down to "REACTION OF RMgX WITH AN ESTER"
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch20reactionsesters.html

Acyl halides will also have grignard added twice.
I think anhydride as well(Check on it)

 

[babowc]

In this case with an ester, it'll add the grignard twice.

For the step by step mechanism: Scroll down to "REACTION OF RMgX WITH AN ESTER"
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch20reactionsesters.html

Acyl halides will also have grignard added twice.
I think anhydride as well(Check on it)

Awesome.. I just took Ochem2 and my professor did not bother explaining this. 👎
Thanks a bunch!

I can't find the acid anhydride adding twice, I'll keep looking and report back

 

[Moka11]

For the record the answer was E right? Cause Methyl Lithium should attack once giving the same product.

 

[KyoPhan]

I can't find the acid anhydride adding twice, I'll keep looking and report back

I found it here:
"Grignard reagents will also add to esters. What makes these reactions a little more complicated is that they add twice. The net result (after addition of acid) is a tertiary alcohol. This is also the case for acid halides (acyl halides) and anhydrides."
http://www.masterorganicchemistry.com/2011/10/14/reagent-friday-grignard-reagents/

But I can't find it anywhere else.

 

[babowc]

For the record the answer was E right? Cause Methyl Lithium should attack once giving the same product.

Yup

I found it here:
"Grignard reagents will also add to esters. What makes these reactions a little more complicated is that they add twice. The net result (after addition of acid) is a tertiary alcohol. This is also the case for acid halides (acyl halides) and anhydrides."
http://www.masterorganicchemistry.com/2011/10/14/reagent-friday-grignard-reagents/

But I can't find it anywhere else.

Awesome.. I'll keep that in mind. Thanks again!
I'm just working through the entire Orgo odyssey. Ochem and GC are my weakest subjects, because it's been nearly 2-3 years since I took Ochem 1 and GC1/2.