ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 27, Problem 27.13P
Show that a thermal suprafacial addition is symmetry allowed in a
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Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reactiontakes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of theproduct isomerizes to the exo isomer at 90 °C.furan: O maleimide:OON H(a) Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.(b) Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.(c) Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled orone that is thermodynamically controlled, or both.(d) Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °C
23. For the alkenes shown below, consider the symmetry properties of the HOMO and the LUMO
and decide whether this concerted cycloaddition reaction is likely to occur.
CH2=CH2
CH2=CH2
Why does a [2+2] cycloaddition reaction require a thermal condition to be
met for initiation?
Chapter 27 Solutions
ORGANIC CHEMISTRY
Ch. 27 - Prob. 27.1PCh. 27 - Problem 27.2
For each molecular orbital in Figure...Ch. 27 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4
(a) How many molecular orbitals are...Ch. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.7PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10P
Ch. 27 - Problem 27.11
What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13
Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18
Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
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- Which of the following dienes have an s-cis conformation, and which have an s-trans conformation? Of the s-trans dienes, which can readily rotate to s-cis?arrow_forwardFor the following dienes, identify whether the molecules has any cis or trans stereochemistry and idenfity the conformation as either s-cis or s-trans, where appropriate. Please also note whether the compound would be reactive in a Diels -Alder reactionarrow_forwardThe 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.arrow_forward
- Which of the following statments is TRUE about the Diels-Alder cycloaddition reaction? The best reactions occur with an electron-rich diene and an electron-poor dienophile. The reaction favors the exo-product. Entropy drives the reaction toward the cyclohexene product. The reaction is not stereospecific with respect to the dienophile stereochemistry.arrow_forwardChoose the correct option. 1. Which of the following reactions best describes the Diels-Alder reaction?A)electrocyclic reactionB)cycloaddition reactionC)sigmatropic reactionD)radical reactionE)nucleophilic substitution reaction 2.Which of the following statements best describes the theory of Conservation of Orbital Symmetry?A)Molecular orbital of the transition state must be similar to that of the reactant.B)Molecular orbital of the transition state must be similar to that of the product.C)Only s orbitals from reactants and products are utilized.D)Molecular orbitals of reactant and product must have similar symmetry.E)Molecular orbitals of reactant and product must have different symmetry. 3.Through what type of single pericyclic reaction did the reaction proceed? 5-methylcyclopenta-1,3-diene to 1-methylcyclopenta-1,3-dieneA)[1,2] sigmatropic hydrogen migrationB)[1,3] sigmatropic hydrogen migrationC)[1,4] sigmatropic hydrogen migrationD)[1,5] sigmatropic hydrogen migrationE)none of the…arrow_forwardWhich of the following statements about cycloaddition reactions is not true? Cycloaddition reactions form a cyclic product with two new bonds. The course of the reaction is determined by the symmetry of the molecular orbitals of the products. Cycloaddition reactions are concerted. Cycloaddition reactions are stereospecific.arrow_forward
- Predict the product where cyclohexadiene does a Diels-Alder with itself.arrow_forwardThe rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forwardThis 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.arrow_forward
- ] Draw the structure of Diels-Alder cycloadduct formed via an endo 3. [a, transition state structure involving the diene and dienophile shown here. [b Formulate the endo transition structure that leads to the product. [c is observed. Does it correspond to a primary or a secondary KIE? Explain. [d. the 'inverse' variety? Explain. -CO2ET ]A KIE ] Is the KIE of the 'normal' orarrow_forwardCompare the relative stability of Dewar’s benzene (bicyclo[2.2.0]hexa-2,5-diene) and benzene with respect to benzvalenearrow_forwardDraw the retro Diels–Alder mechanism for the product shown in Problem 24.50.arrow_forward
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