/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q12P. Question. Propose a mechanism fo... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Question. Propose a mechanism for the acid-catalyzed condensation of n-propyl alcohol to n-propyl ether, as shown above. When the temperature is allowed to rise too high, propene is formed. Propose a mechanism for the formation of propene and explain why it is favored at higher temperatures.

Short Answer

Expert verified

Answer

The formation of propene from n-propyl alcohol occurred at higher temperatures due to favourable conditions like increased entropy favours dehydration reaction.

Step by step solution

01

Acid-catalyzed condensation of alcohol

In acid-catalyzed condensation, the first step is the acidic proton abstraction of acid by oxygen and converts OH into the water, which is a good leaving group.The second step involves the attack of carbocation by alcohol, and by neutralization reaction, we get an ether compound.

02

Acid-catalyzed condensation of n-propyl alcohol

In acid-catalyzed condensation of n-propyl alcohol, the first step is the abstraction of acidic proton of acid by oxygen which converts the hydroxyl group into the water, a good leaving group. Then, the second molecule of n-propyl alcohol attacks carbocation, which is generated after the removal of water and lastly, the neutralization reaction, which stabilizes the positive charge on oxygen and n-propyl ether, gets formed.

Acid-catalyzed condensation of n-propyl alcohol

03

Formation of propene from n-propyl alcohol

The formation of propene occurs at higher temperatures during acid-catalyzed condensation of n-propyl alcohol, and this is because, as temperature increases, the entropy term becomes important. As the number of molecules increases, entropy also increases. In ether formation, entropy is small due to no net change in the entropy as two molecules of alcohol gives one molecule of ether and one molecule of water. In dehydration, one molecule of alcohol generates one molecule of alkene and one water molecule; thus, entropy increases in the system. The reaction shifts towards dehydration instead of condensation at higher temperatures.

Formation of propene at higher temperatures from n-propyl alcohol

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Question. Glycerol (propane-1,2,3-triol) is a viscous syrup with molecular weight 92g/mol, boiling point 290oC, and density 1.24g/mol. Transforming the three hydroxy groups into their trimethylsilyl ethers (using chlorotrimethylsilane and a tertiary amine) produces a liquid that flows easily, has molecular weight 309g/mol, boiling point approximately 180oC, and density 0.88g/mol. Draw the structures of these two compounds and explain why glycerol has a lower molecular weight but a much higher boiling point and density.

Show the rest of the mechanism for formation of cyclized intermediate in figure 14-6.

Role of squalene in the biosynthesis of steroids. The biosynthesis of steroids starts with epoxidation of squalene to squalene-2,3-epoxide. The opening of this epoxide promotes cyclization of the carbon skeleton under the control of an enzyme. The cyclized intermediate is converted to lanosterol and then to other steroids.

Predict the products of the following reactants. An excess acid is available in each case.

(a) Ethoxycyclohexane + HBr (b) tetrahydropyran + HI

(c) anisole ( methoxybenzene) + HBr

(d)

(e)

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.

(b)Propose a mechanism for this reaction

Show how you would synthesize the following ethers in good yields from the indicated starting materials and any additional reagents needed.

(a) Cyclopentyl n propyl etherfromcyclopentanolandpropan-1-ol.

(b) n-butyl phenyl etherfromphenolandbutan-1-ol.

(c) 2-ethoxyoctanefrom anoctene

(d) 1-methoxydecanefrom adecene

(e) 1-ethoxy-1-methylcyclohexanefrom 2-methylcyclohexanol.

(f) trans-2,3-epoxyoctane from octane-2-ol.

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.