Draw the structure of the product of the Diels-Alder reaction below. CH3 a CH3 + 8 CH3OC-C=C-COCH3 Fa ICLOCH₂ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it. • If the reaction produces a racemic mixture, just draw one stereoisomer.

Draw the structure of the product of the Diels-Alder reaction below. CH3 a CH3 + 8 CH3OC-C=C-COCH3 Fa ICLOCH₂ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it. • If the reaction produces a racemic mixture, just draw one stereoisomer.

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.33P

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True or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.
Draw the structure of the product of the Diels-Alder reaction below. CH3 O Visited (+ CH3 90-85 + • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it. • If the reaction produces a racemic mixture, just draw one stereoisomer. CH3OC-C=C-COCH3 O [ ] در ? Previous Frail Instructor Save
1. Compare the electron density maps for the two compounds. (They were both created using the same color scale.) There is more electron density around the oxygen in cycloheptatrienone compared to the oxygen in cyclopentadienone. Explain the difference. Cycloheptatrienone Cyclopentadienone 2. One of your labs in CHM2211L uses cyclopentadiene as a reagent in a Diels-Alder reaction. However, before it can be used in that reaction it must be heated and distilled as the compound dimerizes while it is stored. Draw the dimerization reaction in bond line form. 3. Is the following compound aromatic? Detail how it meets or does not meet the qualifications of aromaticity. If it is not aromatic, could it easily be converted into an aromatic compound? How? H CX H
Draw the major product of the following Diels-Alder reaction. Use the Bicyclic ring tool and guide points to draw bicyclic molecules. D + O Click and drag to start drawing a structure. : m 山

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Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown CH3CH2O. Diene + Dienophile Co,CH3 •Consider E Z stereochemistry of alkenes. •Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the sign from the drop-down menu. C. P. opy aste %3D
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1. Consider the Diels-Alder cycloaddition reaction below. D heat H D = deuterium = 2H Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw appropriate resonance structures and explain why only one constitutional isomer is expected to form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to be endo and the other has to be exo.
Draw one enantiomer of the major product of the following Diels- Alder reaction. (Use wedge/dash bonds to indicate the orientation of substituents in the product. Hydrogen atoms on chirality centers must be shown explicitly.) H.
Draw the structure of the product of the Diels-Alder reaction below. H3C CH3 O || O || + CH3OC-CEC-COCH3
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