Question about a OCHEM synthesis problem?

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p15tolpete

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  1. Pre-Pharmacy
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This is for a problem I had on my test in Organic 1. I know its not PCAT but was curious to see if what I did was correct and figured students studying for their PCAT's would have ochem fresh on their mind. I had never practiced a synthesis that didnt split into smaller parts.

http://imageshack.us/photo/my-images/713/img0785nf.jpg/
img0785nf.jpg
 
Everything looks fine except for the second step. A strong base (like NaH) should be used instead of an acid, deprotonating the alcohol, leaving an insoluble salt O-(Na+), which will then SN2 attack the carbon directly attached to Br (of the 3-(2-Bromoethyl) substituent) to form the cyclic ether.

Adding acid to the first product will result in the alcohol being protonated and therefore a water molecule will leave and an alkene will form instead within the cyclohexane structure.
 
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