Under milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.

Under milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.51P: In this chapter, we studied the mechanism of the acid-catalyzed hydration of an alkene. The reverse...

See similar textbooks

Similar questions

1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. Propose a mechanism for this reaction.
Acid-catalyzed dehydration of 3-methyl-2-butanol gives three alkenes: 2-methyl-2- butene, 3-methyl-1-butene, and 2-methyl-1-butene. Propose a mechanism to account for the formation of each product
The acid-catalyzed hydration of 3,3-dimethyl-1-butene gives 2,3-dimethyl- 2- butanol as the major product. Propose a mechanism for the formation of this alcohol
The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
The pyrolysis of acetic esters to give an alkene and acetic acid is thought to involve a planar transition state and cyclic redistribution of (4n + 2) electrons. Propose a mechanism for pyrolysis of the following ester.
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:
What are the three alkenes formed in the acid-catalyzed dehydration of 2-pentanol? Propose the mechanism of their formation.
Starting with acetylene and ethylene oxide as the only sources of carbon atoms, show how to prepare the compound Q.)1,6-Hexanediol
1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol.(a) Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.
Alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzene
When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation. Predict which of the three alkenes is the major elimination product