The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.

The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter10: Organohalides

Section10.SE: Something Extra

Problem 38AP

See similar textbooks

Related questions

Q: For the following dienes, identify whether the molecules has any cis or trans stereochemistry and…

Q: Luminol dianion is treated with hydrogen peroxide and potassium ferricyanide which results in…

Q: What is the expected rate law and mechanism for this square planar substitution reaction?

A: Given reaction:

Q: i need help analyzing the experiment Experimental Procedures in bullet points Raw Data left blank…

A: The Diels-Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene…

Q: Predict the major product for the following Diels-Alder reaction. Clearly indicate the…

A: Diels-Alder reaction is a cycloaddition of suitable diene and a dienophile to form a six membered…

Q: Predict the product for the following Diels-Alder reaction. сосн,

A: We have given the organic reaction and we have to find the major product of the reaction.

Q: Give the structure(s) of the product(s) of each reaction. Indicate any relative stereochemistry,…

A: Given that : We have to give the structure(s) of the product(s) of each reaction :

Q: Dimethyl azodicarboxylate takes part in a DielsAlder reaction as a dienophile. Write the structure…

A: The solution is given below -

Q: Describe the ground-state electron configuration of the cycloheptatrienyl radical and anion.…

Q: Cyclopentadiene is unusually acidic for a hydrocarbon. Which of the following explains why that is?…

A: The solution is given below -

Q: Draw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction.…

A: The reaction between a conjugated diene and a dienophile (which is an alkene) gives cyclohexene or…

Q: Aromatic compounds also known as arenes or aromatic are chemical compounds that contain conjugated…

A: In this question, we have to find out the correct answer of given problem by the help of the…

Q: two positions of anthracene sometimes react more like polyenes thanlike aromatic compounds.(a) Draw…

A: In case of anthracene, C9 and C10 involve in the diels-alder reaction.

Q: Draw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction.…

Q: Predict the electronic configurations of (a) the benzeneanion, (b) the benzene cation. Estimate the…

A: The benzene anion has 7 -electrons and the benzene cation have 5 -electrons. The electronic…

Q: Select the conjugated diene which cannot undergo the Diels-Alder reaction.

A: The Diels–Alder reaction can be described as a chemical reaction in which a conjugated diene reacts…

Q: Draw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction.…

A: Diels Alder reaction is the cycloaddition reaction between diene and dienophile. This is also known…

Q: For the Diels–Alder reaction, the product's skeletal structure and configuration at the bridgehead…

A: Diels-Alder reaction is a cycloaddition reaction in which diene and dienophile react together to…

Q: Indicate the structures of the dienes and phyllodes that give rise to the Diels-Alder adducts:

A: Diels alder reaction is an example of pericyclic reaction in which diene and dienophile is involved.

Q: The following compound can carry out the Diels-Alder reaction ,dilute the structure of the C4H6…

A: A problem based on spectroscopy, which is to be accomplished.

Q: Which of the following is a sigmatropic rearrangement? *

A: A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one…

Q: Why is the diels alder reaction important? What is a compound that would be not possible to…

A: 1. Diel Alders reaction is important to synthesize cyclic compounds (i.e. cyclohexenes) of different…

Q: When heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen…

Q: What reactants are necessary for the synthesis of the following compound via a Diels-Alder reaction?

A: In the Diels-alder reaction, diene and dienophile undergo thermally-allowed [4+2] cycloaddition…

Q: Predict the product where cyclohexadiene does a Diels-Alder with itself.

A: Diels-Alder reaction : It is a [4+2] cycloaddition reaction between a diene and a dienophile in the…

Q: Draw a structural formula for the product of this Diels-Alder reaction, including the…

A: A reaction of conjugated dienes with double bonded (or) triple bonded compounds known as dienophiles…

Q: а. A Meo CN OMe Meo,C b. A CO̟Et с. Br2 hv

A: "since you have posted a question with multiple sub-parts, we will solve the first three sub-parts…

Q: This is a Diels-Alder reaction between furan + maleic anhydride (endo and exo products). For each…

Q: Perhaps it is unsurprising that cyclohexane and ethanol are reasonable UV solvents, whereas toluene…

A: Here we will discuss about the UV spectroscopy and the solvents used in it.

Q: Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the same…

A: The delocalization energy is the extra stability a compound has as a result of having delocalized…

Q: Organometallic compounds such as magnesium and lithium are characterized by the C-M bond. Explain in…

A: Organometallic compounds such as magnesium and lithium are characterized by the C-M bond. They are…

Q: Which of the following is the most plausible product for this Diels-Alder reaction?

A: Diels alder cycloaddition reaction is also called 4+2 cycloaddition. This reaction occurs between…

Q: Please draw out the structures of compound A, B, C, D and E. The formula of Compound A is C5H6.…

A: This is question of reaction mechanism.In this mechanism oxidation, Electrophilic addition reaction…

Q: (c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic…

Q: What kind of compounds are prepared using the Diels Alder reaction?

A: Diels-Alder reaction: The Diels–Alder reaction is a pericyclic reaction (cycloaddition) between a…

Q: which of these cannot undergo a diels-alder reaction as the diene?

A: The 4+2π cycloaddition reaction of compounds is known as the Diels-Alder reaction. The dienophile…

Q: Explain why butadiene sulfone was used in the Diels-Alder reaction with maleic anhydride? Why is…

Q: Draw a structural formula for the product of this Diels-Alder reaction, including all stereoisomers…

A: Diels Alder reaction also known as( 4+2 )π electron cyclo addition.

Q: Why does the diels alder reaction often show high selectivity and predictable stereochemistry?

A: Pi bonds are converted into stronger sigma bonds, the reaction is thermodynamically favourable. The…

Q: The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product.…

Q: Under certain conditions, 1,3-butadiene can function as both a diene and a dienophile. Draw a…

A: The Diels-Alder reaction is a conjugate addition reaction of a conjugated diene to an alkene or an…

Q: Draw an orbital correlation diagram for the suprafacial-suprafacial reaction of an allyl species…

A: We have to draw an orbital correlation diagram for the suprafacial suprafacial reaction of an alkyl…

Q: Which of the structures below is the major product obtained from the following Diels-Alder reaction.…

A: To determine the major product with stereochemistry of the given reaction.

Q: involves

A: This question is related to diels alder reaction.

Q: In the dehydrohalogenation of bromocyclodecane, the major product is cis -cyclodecene rather than…

A: In the dehydrohalogenation of bromocyclodecane, cis-cyclodecene and trans-cyclodecene are formed.

Q: H3C CH3 H3C. CH3 CH3 Br H3C Br

Q: Indicate how each of these compounds could participate in a Diels-Alder reaction. COOH COOH

Q: cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical…

Concept explainers

UV Visible Spectroscopy

Spectroscopy refers to the absorption or emission of light or other radiations by matter. When a substance or chemical absorbs light or radiation, they reach an excited state followed by de-excitation or emission of the light or radiation forming distinct spectra. UV-visible spectroscopy or ultraviolet-visible refers to the absorption and emission in the ultraviolet and visible regions of the electromagnetic spectrum.

Question

The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete
the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.
Select
Draw
Rings
More
Erase
C
160 °C
+
24h

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1 Diels-Alder reaction

VIEW

Step 2 Product

VIEW

Step 3 Conclusion

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Which constitutional isomer represents the product of this Diels-Alder reaction?
The Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.
Predict the product(s) of the following Diels-Alder reaction. Include stereochemistry if appropriate.
Uemura and coworkers studied a time dependent Diels-Alder reaction which first formed the endo product as the major organic product and with time produced the exo product (J. Org. Chem. 2018, 83, 9300−9304). Show the endo and exo product for the reaction below. Which is the thermodynamic product and which is the kinetic product? Explain your reasoning.
The bicyclic alkene P can be prepared by thermal electrocyclic ringclosure from cyclodecadiene Q or by photochemical electrocyclic ringclosure from cyclodecadiene R. Draw the structures of Q and R, andindicate the stereochemistry of the process by which each reactionoccurs.
The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R. Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.
Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.
Predict products of each Diels-Alder reaction (including stereochemistry)
This is a Diels-Alder reaction between ethylene and cis-1,3-butadiene. For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.
Define about Sigmatropic Rearrangements ?
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alderadduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and abroad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings ofanthracene reacted as a diene
What product(s) would be obtained from the Diels-Alder reaction of transCH3CH=CHCO2Et with EACH of the following dienes:(a) 1.3- Butadiene(b) Isoprene(c) Cyclopentadiene________________________________