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- 4. (40 pts) Provide the bond line structure and IUPAC name for the major organic product obtained in each step: HBr (1R, 2S) 1,2,2-trimethyl- ---------> A 6-phenylcyclohexanol KOtertBu HOtertBu HBr peroxides Mg ether ethylene oxide H₂O B > C D E Product Bond line structure IUPAC nameCH3 CH3 CH3 CH;=ĊCH,CHCH;OH H2SO4, H3C H3C Referring to the above reaction: 1. Which atom does the H2SO4 first remove? 2. Identify the reaction if it's hydrogenation, hydrohalogenation, etc. 3. Propose a mechanism for the reaction, using the arrow formalism to indicate the flow of electrons.Draw all resonance structures of the radical that results from abstraction of a hydrogen atom from the antioxidant BHA (butylated hydroxy anisole).
- 6. What are the line structures of compounds E and F in the following sequence of reactions? 0 Compound E L NINH,NH, 2. CH₂CH₂Br Compound F H₂O, H₂SO₂ HgSO; CH₂CH₂CCH₂CH₂CH₂1. Draw the structure of all reactants and product for the following reactions. (a) 2-methyl-1-iodocyclopentane + NaOCH3 ------>A (b) A + (1) Hg(OAc)2, H2O/(2) NaBH4 ------>4. The rearrangement reaction shown below was discovered in 1860. (a) Draw a mechanism for this transformation. Draw in lone pairs, use curved arrows to show movement of electrons, and indicate the formal charge on all charged atoms. (b) Explain why this rearrangement occurs. (Hint: What type of intermediate forms?) но он H2SO4 (conc.) Heat (c) The same type of reaction was used to accomplish the transformation below. Draw the mechanism for this transformation as well. OH H2SO4, heat но
- 12. (10 pts) Under the right conditions radical bromination of A produces compound B as shown below (this is termed allylic bromination): hv Br Br2 A B Write a detailed mechanism for the propagation steps of the above radical bromination, showing how the products are formed and that the radical used in the first step is formed in the last step (use curved arrows to show electron flow).(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).Draw all possible resonance
- U, NH, 14.) The shown reaction is an example of: (A) anti addition, forming a Z-alkene (B) anti addition, forming an E-alkene (C) syn addition, forming a Z-alkene (D) syn addition, forming an E-alkene (E) both A and Care true I11. (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).complete the following synthesis
