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posted by  Ally Jay on 11/16/2008 7:22:18 PM  |  status: Live  

Orgo help needed! please =]

Course Textbook Chapter Problem
Organic Chemistry N/A N/A N/A
Question Details:
Synthesizing ethers via acid-catalyzed condensation reactions has limited usefulness. The conditions (sulfuric acid and heat) are also conducive to elimination products. Primary alcohols will undergo dehydration to ethers at lower temperatures than dehydration to alkenes. Secondary and tertiary alcohols will give predominantly alkene products at the same temperature primary alcohols condense to give ethers. Primary alcohol condensation to ethers is also only useful when the ether is symmetric. The following question is to demonstrate the mess you would get if you tried to synthesize an asymmetric ether via acid-catalyzed dehydration. What two alcohols would you use if your goal was to synthesize hexyl pentyl ether via acid-catalyzed dehydration of two alcohols?


(a) Draw the skeletal structure of the alcohol with the least number of carbons.





(b) Draw the skeletal structure of the desired ether.





Two other ethers will also be produced.
(c) Draw the skeletal structure of the undesired ether with the least number of carbons.





Two elimination products will also need to separated out of the product mixture.
(d) Draw the skeletal structure of the undesired elimination product with the least number of carbons.

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posted by Nicholas(MND) on 11/17/2008 11:30:56 PM  |  status: Live
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Ally Jay's comment:
"THANKS! =D"
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