Illustrate the carbocation pathway for the following reactions + HCI + CH3-OH + H20 (acid-catalyzed) Present the 3-membered ring pathway for the following reactions. Cl2 Br CH3OH Illustrate the concerted pathway for the following reaction. H2 Pt
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.1) LiAlH4; ) H3O+ will do which of the following reactions? 3-Phenyl-butanoic acid → 3-phenyl-butan-1-ol Benzene → cyclohexane Benzoic acid → benzaldehyde 2-Phenyl-hexanoic acid → benzoic acid and carbon dioxide 2,3-dimethyl-pent-1-yne → 2,3-dimethyl-pent-1-eneProvide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IV
- Q17. Compound 1 can undergo an intramolecular reaction to give cyclic product 2. Using curly arrows, show the mechanism of this reaction – note that the mechanism involves more than one elemental step - and draw the structure of 2; chemical formula is provided as guidance. H2N. C5H9NO CH;OH 21. 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 ------>a) Provide a mechanism that accounts for the product formed in the following reaction. OH CH H" ► 1-ethoxy-1-methyleyclohexane + CH,CH,OH b) Show the structure of the product(s) formed in the following reaction and write the mechanism for the reaction. OH CH + (CH;);COH
- 4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH31) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3Q17. Compound 1 can undergo an intramolecular reaction to give cyclic product 2. Using curly arrows, show the mechanism of this reaction – note that the mechanism involves more than one elemental step - and draw the structure of 2; chemical formula is provided as guidance. H,N. CsHgNO + CH;OH 2
- CH3 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.Step 4: In an acid-catalyzed epoxide ring opening, the epoxide is first protonated and can then be attacked by weak nucleophiles. H HO: :Nuc Nuc Weak nucleophiles such as water and alcohols can react with the protonated epoxide. One of the main differences between base-catalyzed and acid-catalyzed epoxide ring openings is the regiochemical product expected. In an acid-catalyzed reaction, if one of the epoxide carbons is tertiary and the other primary, the nucleophile will attack at the more substituted carbon. If the epoxide is monosubstituted, the nucleophile will attack preferentially at the primary carbon vs. the secondary carbon. Which reaction will not give the indicated product? N 1. CH,CH,O 2. H₂O OH CH₂CH₂OH, H* N CH₂CH₂OH, H 1 CHICH,O 2. H₂O HO HO H- HAddition proceeds preferentially through the most stable carbocation intermediate. At high temperature, 10-20 °C or higher, products equilibrate; and the most stable product predominates (thermodynamic control). At low temperature, 0 °C or lower, there is kinetic control of reaction products. CI CI b Write a mechanism for the first step of this reaction using curved arrows to show electron reorganization. Consult the arrow-pushing instructions for the convention on regiospecific electrophilic attack on a double bond. Arrow-pushing Instructions n →XT H-CI: