a) The following two cyclobutenes 4 and 5 can be opened to form diene structures thermally, however one reacts much slower than the other. Which of 4 or 5 reacts faster and which slower, and why? Use suitable diagrams to illustrate your answer. 4 5 b) HARD: Both 4 and 5 can also react photochemically to give one monocyclic product each, isomeric with the starting materials. Draw the structures of the products and rationalize their formation. (HINT: Electrocyclization reactions are NOT involved in the formation of the monocyclic products.)

a) The following two cyclobutenes 4 and 5 can be opened to form diene structures thermally, however one reacts much slower than the other. Which of 4 or 5 reacts faster and which slower, and why? Use suitable diagrams to illustrate your answer. 4 5 b) HARD: Both 4 and 5 can also react photochemically to give one monocyclic product each, isomeric with the starting materials. Draw the structures of the products and rationalize their formation. (HINT: Electrocyclization reactions are NOT involved in the formation of the monocyclic products.)

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.27P: Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both...

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74. 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 piperidine
5. When the diene below is dissolved in THF solvent to which a small amount of H₂SO4 has been added, cyclic products are formed that are isomeric with the reactant. Write a mechanism for the formation of ONE of these cyclic isomers, and include its structure. (In other words, you predict the product structure by going through the mechanism.) Include curved arrows in the mechanism to show bonding changes. yand H₂SO4 THF A cyclic isomer of the reactant
2) Rank the following dienes by how rapidly they will undergo Diel-Alder reactions with ethylene.
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4. Isit possible for the diene shown below to undergo a Diels-Alder reaction with maleic anhydride? Explain.
which of the following general statements is true about the addition of HBr to conjugated dienes (A) At low temperature, the 1,2-adduct predominates (B) At low temperature, the 1,4-adduct predominates (C) At high temperature, the 1,2-adduct predominates (D) Temperature does not affect the outcome of the reaction
d) How many electrons and what conditions are involved in the following concerted reaction? DH A) 4 electrons, an even number of nodes, hv B) 6 electrons, an odd number of nodes, hv C) 6 electrons, an even number of nodes, heat D) 4 electrons, an odd number of nodes, heat f) Which diene below cannot readily undergo Diels Alder chemistry? B. h) The following is dimer formed from two trioses. The trioses are HQ OH OH HO A. D-glyceraldehyde and 1,3-dihydroxyacetone B. L-glyceraldehyde and 1,3-dihydroxyacetone C. D-glyceraldehyde and L-glyceraldehyde D. 1,3-dihydroxyacetone and 1,3-dihydroxyacetone HH answer [
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-A on 2. Which class of pericyclic reactions is the Diels-Alder reaction? What is a (4+ 2) n cycloaddition reaction? Explain •a cycloaddikon where ore reactant moleculee cortriautes 41 ele ctrons & the other a electrans 3. 4. (a) Give the systematic name of the diene in this reaction 15-cis)1,4-diphenyl-1,3-betadiene (b) Calculate the difference in the standard Yree energy, AG° (kJ/mol) between the two major conformations of this diene? (Write the formula and show your work.) = (-617.920458au- AGO Product- reactants k017.9259320 = 0.00S 47444K/ml.005474qu 14.37 KJ/ mol 1au= alas.KLcis) (trans) 5. Give the systematic name of the dienophile in this reaction. Maleie nhydride 6. Give the systematic name of the adduct in this reaction. 7. What is the melting point of your synthesized Diels-Alder adduct 8. Calculate the standard free energy of activation AG # for this reaction (Write the formula and show your work). AG = G75- G°R = (-994.1304ay au)-(-997.194182 au) - 0.039898au= .639898ay•…
1-Explain why the reactivity is more for primary alkyl halide in SN2 and tertiary alkylhalide in SN1 reaction. 2- differentiate between erythro and threo isomers. What are the condition in addition reaction of alkenes to get a erythro products. 3- what is the condition of any compound to be optically active?
Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?