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- 5) Provide the expected mechanism for the following reaction. Please show all intermediates and use arrows to show the movement of electrons (you do not have to show transition states). (1 pt) ii CI NaOH (2 equiv)5. Which product is formed in the following reaction? OH KCrO, 77 OH (e) (b) (c)Draw structural formulas for the isomeric carbocation intermediates formed on treat- ment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of the isomeric carbocations forms more readily. CH₂CH3 (a) H₂C=C (c) CH3 CH3 (b) (d) H₂C-CH=CH-CH3
- What is the correct sequence of steps for the following transformation? Step 1 Step 2 HO (a) HBr, followed by H20 (b) H2 over Lindlar's catalyst, followed by H2O/H,SO4 (c) H2O/H2SO4/H&SO4, followed by HBr (d) H2 over Pd/C, followed by H20 Which structure corresponds to the missing step in the reaction mechanism for the conversion of the alkene/alcohol to the cyclic ether? HC! H20 + H;O OH OH OH (a) (b) (c) (d)Write the appropriate reagents, conditions and products for the following transformations, in a single step. OH II HNO, ? (1) H,SO,The accepted mechanism for a rearrangement reaction is shown below. "Q Ph (1) (ii) Ph Ph HO™ fast Ph Ph HO O™ slow Ph aufae .Ar² LOH HO™ fast Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. HQ Ph (iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining. Ph (iv) Write the predicted rate equation for this mechanism, and show how it was derived. (v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃ labelling experiment that would allow you to distinguish which of the two aryl groups had migrated in this situation. OH AR²0- Ar¹ C C
- 58. What is the major product of this reaction? Br₂ H3O+ (A) (C) (A) 59. What is the product of this reaction after neutralization? (B) (C) Br or Br (D) HN-CH3 C -CH3 (B) (D) NH₂ Br CH3 N-CH3 HN-CH₂ H3O H₂O Br (C) (A) HO (B) 61. Which conversion is energetically favorable? ok-ob H bi (D) bi - سمه ? (A) (D) ia 62. What starting material will genera product with the given reaction s 1. NaOEt in ethanol HO 2 HO 요. 2. 3. H₂0, H₂O, heat OH OEt 63. What is the monomeric ur polyhydroxy- biodegradab (A) A (C)101. The major product formed in the following reaction sequence GHI Br (a) (b) (i) Br₂, H₂O (ii) H2SO4,A 'Br Br (c) All Bowl Chemistry Br (d)Which of the following is a major product of the reaction sequence below? Br (1) HNO3/H,SO4 NO2 Br (A) H3CO. (B) H3CO (2) Na CH,0 CH:OH OCH3 Br NO2 Br (D) (C) OCH3 NO2 Compound C O Compound B Compound D Compound A
- Treatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.3. Propose the product/s synthesized from following reaction: (a) CHC-CHCH, + HBr ČH, ÓH (b) Propose what reagent you can use to increase product yield and to avoid carbocation rearrangement to occur in 3(a)?(b) Write out the product(s) for the reactions below. Analyze the compounds (i) and (ii) below and classify which one reacts faster. Explain your answer. (ii) H OH SO3 H₂SO4 HNO3 H₂SO4