/*! 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} Q8P Which of the following alkenes w... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 14: Q8P (page 436)

Which of the following alkenes would you expect to be good Diels鈥揂lder dienophiles?

Short Answer

Expert verified

Compound (a) Acryloyl chloride is a good dienophile.

Compound (b) methyl pent-4-enoate is a not good dienophile.

Compound (c) cyclohexene is a not good dienophile.

Compound (d) cyclohex-2-enone is a good dienophile.

Compound (e) cyclo-3-enone is a not good dienophile.

Step by step solution

01

Dienophile

Dienophiles react with diene through 4+2 cycloaddition, forming the cyclic adduct product.

Dienophile reactivity depends on the following factor:

  • Electron-withdrawing group
  • Weak pie bond
  • Release ring strain
02

Compound (a) Acryloyl chloride dienophile

Good dienophiles have an electron-withdrawing group (EWG) conjugated with an alkene double bond.

Compound (a) Acryloyl chloride has the carbonyl group, the electron-withdrawing group. It is also in conjugation with a double bond of the alkene part; therefore, it fulfills both conditions of the good dienophile.

Thus Compound (a) is a good dienophile

03

Compound (b) Methyl pent-4-enoate  dienophile

Good dienophiles have an electron-withdrawing group (EWG) conjugated with an alkene double bond.

Compound (b) methyl pent-4-enoate has the carbonyl group, the electron-withdrawing group, but the carbonyl group is not conjugation with a double bond of the alkene part; therefore, it does not fulfill both conditions of the good dienophile.

Thus Compound (b) is not a good dienophile.

04

Compound (c) Cyclohexene dienophile

Good dienophiles have an electron-withdrawing group (EWG) conjugated with an alkene double bond.

Compound (c) cyclohexene doesn't have any electron-withdrawing group and no conjugation present in the Compound. It does not fulfill any condition of a good dienophile.

Thus Compound (c) is not a good dienophile.

05

Compound (d) Cyclohex-2-enone dienophile

Good dienophiles have an electron-withdrawing group (EWG) conjugated with an alkene double bond.

Compound (d) cyclohex-2-enonehas the carbonyl group, the electron-withdrawing group, and the carbonyl group is conjugated with a double bond of the alkene part; it fulfills both conditions of the good dienophile.

Thus Compound (d) is a good dienophile.

06

Compound (e) Cyclo-3-enone dienophile

Good dienophiles have an electron-withdrawing group (EWG) conjugated with an alkene double bond.

Compound (e) cyclo-3-enonehas the carbonyl cyclo-3-enone has a carbonyl electron-withdrawing group, but the carbonyl group is not conjugation with a double bond of the alkene part; therefore, it does not fulfill both conditions of the good dienophile.

Thus Compound (e) is not a good dienophile.

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 91影视!

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

Give the structures of both 1,2 and 1,4 adducts resulting from reaction of 1 equivalent of HBr with the following compound:

Treatment of 3,4-dibromohexane with strong base leads to loss of2 equivalents of HBr and formation of a product with formula C6H10.Three products are possible. Name each of the three, and tell how youwould use 1H and 13C NMR spectroscopy to help identify them. Howwould you use UV spectroscopy?

Predict the product of the following Diels鈥揂lder reaction:

The 1,2 adduct and the 1,4 adduct formed by reaction of HBr with 1,3-butadiene are in equilibrium at 40 掳C. Propose a mechanism by which the interconversion of products takes place.

Addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures to explain whynone of the other regioisomer is formed.
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Making Measurements

Read Explanation

Chemical Analysis

Read Explanation

Inorganic Chemistry

Read Explanation
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.