Concept explainers
Interpretation:
Structural formulas for all the conjugated, isolated, and cumulated dienes that give
Concept introduction:
Catalytic hydrogenation is the addition of two atoms of hydrogen to a double bond. A compound with two double bonds undergoes catalytic hydrogenation, then there will be addition of four atoms of hydrogen.
This reaction occurs in the presence of platinum, palladium, nickel, or rhodium. One molar equivalent of hydrogen, when added to
Conjugated dienes contain two
Isolated dienes contain two
Cumulated dienes contain two
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ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
- The Wittig reaction can be used for the synthesis of conjugated dienes as the example below, 1-phenyl-penta-1, 3-diene. Propose two different sets of reagents that could be combined in a Wittig reaction to give 1-phenyl-1,3-pentadiene.arrow_forwardAlthough the Diels–Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.arrow_forwardORGANICarrow_forward
- [3] Reaction of either 3-bromo-1-butene or (Z)-1-bromo-2-butene with water under S,1 condition yields the same product. Explain whyarrow_forwardPlease provide the name of the dienes and dienophiles, and their products and explain the reaction that took place in each item.arrow_forwardDraw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form productarrow_forward
- The highly reactive triple bond of benzyne is a powerful dienophile. Predict the productof the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) withcyclopentadiene.arrow_forwardThere is TWO Blanks, what should I put in them?arrow_forwardDraw structural formulas for the product of reaction of cyclopentadiene with dienophile.arrow_forward
- Following is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.arrow_forward74. When piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substituted piperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and 3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene? 1. еxcess CHз!/К2CO3 2. Ag20, H20 3. Д 1. еxcess CHз!/K2CO3 2. Ag20, H20 CH3NCH,CH,CH;CH=CH2 3. A CH2=CHCH2CH=CH2 || `N' H CH3 1,4-pentadiene piperidinearrow_forwardThe following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction 0"C Diels-Alder adductarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning