Orbital configuration of carbocation (figure 6.3 tButyl cation) energy diagram of a reaction, function of catalyst; intermediates, (enthalpy, activation energy) Markovnikov regioselectivity Anti-/syn-addition
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- A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.5. Classify the following reagents as either nucleophiles or electrophiles: Zn? CH;NH, , HS , OH; , CH;COOH , H,SO,Electron pairs CH3 .. Erase H3C - С — СІ: H3C – S- CH3 CH3 CH, CH3 THF/H,0 + H,C--CH, CH C- CH CHs CH, Use curved arrows to write the first step of this nucleophilic substitution mechanism. :ö: | :ö:
- 7. Complete the following reactions of alkenes and alkynes by provi missing reactant, reagent or product. Do not rewrite the reaction requiredENVVIEW top [References] Draw the structure(s) of the major organic product(s) of the following reaction. Ag,0 / aqueous THF,0° • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. . .None
- Is the reaction stereoselective? Does the reaction of bromine with trans-cinnamic acid involve syn-addition, anti-addition, or both? Explain your reasoning.11) a) How many different molecules containing one double bond can be used to synthesize 4-methyl-4-heptanol (as the major product) via acid catalyzed hydration with H2SOe and H20? Draw them all below. b) Are any of the structures in part (a) trisubstituted alkenes? If so, redraw it/them below. c) Label (if possible) the structure(s) in part (b) as either Z or E double bond isomers. Bonus Question: ) Recently, the Gademann research group from the University of Zurich, completed the synthesis of (+)-Peyssonnosol, a complex natural product (shown below on the left) which contains seven stereocenters. Briefly describe what the "(t)" symbol in front of the synthesized natural product name means. Me., Me, Me Me HO. Me Me Synthesized ()-Peyssonnosol Starting Materials Used inSynthesis11. (24 pts) (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal mole-, for H-Br is 88 kcal mole and for H-H is 104 kcal mole. hv Н-Н + Вr-Br 2 Н-Br (b) Calculate the overall AH for the above propagation steps (show all work).
- 2) (4pts) Classify each reaction as addition, elimination, substitution, or rearrangement. A) CH;CH2B LIOH CH;CH2OH LiBr B) CH;CH2CH,Cl CH-CH-CH2 + + HCl C) CH;CH=CH2 H2 CH;CH2CH3 Verdana 10pt B IU A va) How many different molecules containing one double bond can be used to synthesize 4-methyl-4-heptanol (as the major product) via acid catalyzed hydration with H2SO4 and H2O? Draw them all below. b) Are any of the structures in part (a) trisubstituted alkenes? If so, redraw it/them below.11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).
