ADA practice test 2009 #99 Ochem

[monsieurwise]

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I cannot figure out how to do this the synthesis of antispasmodic spasmolytol problem. I have attached a picture.
The answer they gave is C.
Thanks everyone!

 

[cmF]

What the hell? This was definitely not in Chad's videos. It appears to be correct though. This page shows the exact same reaction towards the end (do control + F to search).

 

[monsieurwise]

What the hell? This was definitely not in Chad's videos. It appears to be correct though. This page shows the exact same reaction towards the end (do control + F to search).

Thanks for the link =). But it doesn't say why C is the right choice instead of D... This problem really scare the heck out of me, coming from an easier version of the DAT.
Did anyone find an answer?

 

[monsieurwise]

Hmmm I think it's a 2 part problem. First is the opening of the epoxide, and then Fischer esterification because we see that there is a carbon between the O can the aromatic ring. There's no way to do that in D.
Thanks cmF, how did you manage to find that random pdf haha. You must be a Google god =).