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(a)
Interpretation:
The mechanism and the major product of the given reaction is to be drawn, without considering the stereochemistry.
Concept introduction:
The two new sigma bonds fomraton take place by joining a conjugated diene and a dienophile is known as the Diels-Alder reaction (also known as [4+2] cycloaddition). The product is a six-membered ring. The Diels-Alder reaction is concerted, that is, the process of bond breaking and bond formation occurs simultaneously. For a Diels-Alder reaction to take place, the diene must be able to attain the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly regioselective and stereospecific. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.
(b)
Interpretation:
The mechanism and the major product of the given reaction is to be drawn, without considering the stereochemistry.
Concept introduction:
The two new sigma bonds fomraton take place by joining a conjugated diene and a dienophile is known as the Diels-Alder reaction (also known as [4+2] cycloaddition). The product is a six-membered ring. The Diels-Alder reaction is concerted, that is, the process of bond breaking and bond formation occurs simultaneously. For a Diels-Alder reaction to take place, the diene must be able to attain the s-cis conformation. Diels-Alder reactions cannot take place with the diene in the s-trans conformation. Electron-donating groups attached to the diene and electron-withdrawing groups attached to the dienophile facilitates the reaction. These reactions are highly regioselective and stereospecific. Substituents that are cis to each other about the carbon-carbon double bond of the dienophile end up cis to each other in the new ring that is produced. Otherwise, the substituents end up trans to each other in the ring. Substituents attached to the terminal carbons of the diene end up cis to each other in the new ring that is produced if the double bonds of the diene are both cis or both trans. Otherwise, the substituents end up trans to each other in the ring. When the diene and dienophile are both unsymmetric, two isomeric products can be produced.
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Chapter 24 Solutions
Get Ready for Organic Chemistry
- 7. Draw a curved arrow mechanism for the following reaction. HO cat. HCI OH in dioxane with 4A molecular sievesarrow_forwardTry: Convert the given 3D perspective structure to Newman projection about C2 - C3 bond (C2 carbon in the front). Also, show Newman projection of other possible staggered conformers and circle the most stable conformation. Use the template shown. F H3C Br Harrow_forwardNonearrow_forward
- 16. Consider the probability distribution p(x) = ax", 0 ≤ x ≤ 1 for a positive integer n. A. Derive an expression for the constant a, to normalize p(x). B. Compute the average (x) as a function of n. C. Compute σ2 = (x²) - (x)², the variance of x, as a function of n.arrow_forward451. Use the diffusion model from lecture that showed the likelihood of mixing occurring in a lattice model with eight lattice sites: Case Left Right A B C Permeable Barrier → and show that with 2V lattice sites on each side of the permeable barrier and a total of 2V white particles and 2V black particles, that perfect de-mixing (all one color on each side of the barrier) becomes increasingly unlikely as V increases.arrow_forward46. Consider an ideal gas that occupies 2.50 dm³ at a pressure of 3.00 bar. If the gas is compressed isothermally at a constant external pressure so that the final volume is 0.500 dm³, calculate the smallest value Rest can have. Calculate the work involved using this value of Rext.arrow_forward
- Nonearrow_forward2010. Suppose that a 10 kg mass of iron at 20 C is dropped from a heigh of 100 meters. What is the kinetics energy of the mass just before it hits the ground, assuming no air resistance? What is its speed? What would be the final temperature of the mass if all the kinetic energy at impact is transformed into internal energy? The molar heat capacity of iron is Cpp = 25.1J mol-¹ K-1 and the gravitational acceleration constant is 9.8 m s¯² |arrow_forwardell last during 7. Write the isotopes and their % abundance of isotopes of i) Cl ii) Br 8. Circle all the molecules that show Molecular ion peak as an odd number? c) NH2CH2CH2NH2 d) C6H5NH2 a) CH³CN b) CH3OHarrow_forward
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