Assignment:
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 butyl pentyl ether via acid-catalyzed dehydration of two alcohols?
(a) What is the skeletal structure of the alcohol with the least number of carbons.
(b) What is the skeletal structure of the desired ether.
Two other ethers will also be produced.
(c) What is 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) What is the skeletal structure of the undesired elimination product with the least number of carbons.
Provide complete and step by step solution for the question and show calculations and use formulas.