Making Ethers - Alcohol Condensation Practice Problems
A good way to prepare a symmetrical ether, such as dipropyl ether, is by heating alcohol with sulfuric acid.
Determine how you would synthesize ethyl isopropyl ether.
Using (R)-1-deuterio-1-pentanol as the starting substrate, determine how to prepare (S)-1-deuterio-1-methoxypentane.
One of the products, when an excess of propylene oxide reacts with hydroxide ion, is tripropylene glycol. Provide a possible mechanism for the given reaction.
A good way to synthesize a symmetrical ether like dipropyl ether is to heat an alcohol with sulfuric acid. Explain why it is not recommended to synthesize an unsymmetrical ether such as butyl isopropyl ether in this manner.
Which of the given ethers could be produced directly from alcohols with the highest yield?
Acid-catalyzed condensation is impractical for the synthesis of the unsymmetrical ether shown below. Explain why this is true.
isopropyl propyl ether, (CH3)2CH−O−CH2CH2CH3
Acid-catalyzed condensation of an alcohol gives 2,3,5,6-tetramethyl-1,4-dioxane.
(i) What alcohol undergoes acid-catalyzed condensation to give 2,3,5,6-tetramethyl-1,4-dioxane?
(ii) Suggest a plausible mechanism for the synthesis of 2,3,5,6-tetramethyl-1,4-dioxane.