Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: asd5110 on December 17, 2010, 03:51:46 AM
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Which set of reagents is the best to accomplish the transformation shown above?
A) CH3CH2I/KOH
B) CH3OCH2CH3/H3PO4
C) CH3CH2OH/H2SO4
D) CH3CH2MgBr/ether
E) CH3CH2OK/CH3CH2I
i guessed C but i don't know why the other answer choices wouldn't work
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I think C is wrong because while it fits the requirements of alcohol + acid, it would yield a different isomer. Not sure without actually working the problem out.
Grignard reagents work quite well with epoxide ring openings due to their nucleophilic nature. You might want to give that a shot.
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Grignard wont work. it will attach C2H5 not OC2H5.
Not even A and E as it will give addition if I.
B, C both will work but i guess B will give OCH3 addition rather than OC2H5 addition as major product.
So i think C is most appropriate. :)
correct me if i'm wrong!!!
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C is the correct answer. Many of the other conditions won't even yield the correct product, so you can eliminate them based on that. The reason C is correct is that under acidic conditions, the epoxide will open to yield a carbocation. In the epoxide shown, there are two possible carbocations and one is more stable than the other. You should be able to finish from there.