Given that norbornadiene can be prepared by reaction of chloroethylene with 1,3-cyclopentadiene, followed by treatment of the product with sodium ethoxide. The overall scheme is to be written and the two kinds of the reactions involved are to be identified. Concept introduction: In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction. The reaction takes place in endo manner. On treatment with bases, organic halides dehydrohalogenate to yield alkenes. To write: The overall scheme for preparing norbornadiene by reacting chloroethylene with 1,3-cyclopentadiene, followed by treating the product with sodium ethoxide and to identify the two kinds of the reactions involved.

Question

Want to see the full answer?

Answer 1

Question

Chapter 14.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that norbornadiene can be prepared by reaction of chloroethylene with 1,3-cyclopentadiene, followed by treatment of the product with sodium ethoxide. The overall scheme is to be written and the two kinds of the reactions involved are to be identified.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction. The reaction takes place in endo manner.

On treatment with bases, organic halides dehydrohalogenate to yield alkenes.

To write:

The overall scheme for preparing norbornadiene by reacting chloroethylene with 1,3-cyclopentadiene, followed by treating the product with sodium ethoxide and to identify the two kinds of the reactions involved.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Please help me calculate the undiluted samples ppm concentration. My calculations were 280.11 ppm. Please see if I did my math correctly using the following standard curve. Link: https://mnscu-my.sharepoint.com/:x:/g/personal/vi2163ss_go_minnstate_edu/EVSJL_W0qrxMkUjK2J3xMUEBHDu0UM1vPKQ-bc9HTcYXDQ?e=hVuPC4

Provide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) H₁₂C C(CH3)3 C=C H3C CH3 CH3CH2CH CI CH3 Submit Answer Retry Entire Group 2 more group attempts remaining Previous Next

Arrange the following compounds / ions in increasing nucleophilicity (least to most nucleophilic) CH3NH2 CH3C=C: CH3COO 1 2 3 5 Multiple Choice 1 point 1, 2, 3 2, 1, 3 3, 1, 2 2, 3, 1 The other answers are not correct 0000