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- 8.25 From what alkene was the following 1,2-diol made, and what method was used, epoxide hydrolysis or OsO4? 8.26 Predict the products of the following reactions (the aromatic ring is unreactive in all cases). Indicate regiochemistry when relevant. H₂/Pd Or H (a) (b) (c) (d) (e) (f) Br2 Os04 NMO Cl₂, H₂O →? CH₂I2, Zn/Cu meta-Chloroperoxy- benzoic acid ? ? →?3. following reactions. (a) Draw the product(s) including its(their) stereochemistry in each of the H20 (6) Br cI :8=c-H (i) 1. SOCI, OH 2. CH300 HBr (aq.) (iv) (b) Draw a stepwise mechanism for the formation of products in the reaction below. OH Br (c) Device a synthesis of the product from the given starting material for the following transformation. More than one step is required. ÇI HO.4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro- peroxybenzoic acid followed by H30+. Show the reaction intermediates and the final products with correct cis or trans stereochemistry. 4.36 What products would you expect to obtain from reaction of cyclohexa- 1,3-diene with each of the following? (a) 1 mol Br2 in CH2C12 (c) 1 mol DCl (D = deuterium, ²H) (b) 1 mol HCl (d) 2 mol H2 over a Pd catalyst 4.37 Predict the products of the following reactions on hex-1-yne: (a) 1 equiv HBr ? (b) 1 equiv Cl2 ? (c) H2, Lindlar catalyst
- Predict the major product obtained from each of the following reactions. Show the stereochemistry where pertinent. The starting material for the second step reaction will be the product obtained from first step reaction. Use only major product obtained from the first step to proceed into the second step. (4a) OH (4b) Br Br 1. TSCI/Pyridine 2. NaOEt t-BuOK HBr (1 equiv.) 40 °C HCl (1 equiv.) 0 °C-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.12.13 a) Predict the products of the following reactions and draw mechanisms showing their formation. Br₂ NaHCO. MeOH 1) II) IV) HO OH OH Тон OH OH PCC CH₂Cl₂ H₂CrO₂ H₂O, H₂SO₂ H₂CrO H₂O, H.SO
- 7B. (2 reactions (should clearly indicate the stereochemistry). Draw the structure of the product, substrate or condition in the following (a) ОН (b) Ме 1) OsO4 2) NaHSO3 (c) 1) (sia)2BH 2) NaOH/H2O2 H209.22 Predict the products from reaction of 1-hexyne with the following reagents: (b) 1 equiv Cl₂ (a) 1 equiv HBr (c) H₂, Lindlar catalyst (e) H₂O, H₂SO4, HgSO4 (d) NaNH₂ in NH3, then CH₂ Br (f) 2 equiv HCI 9.23 Predict the products from reaction of 5-decyne with the following reagents: (b) Li in NH3 (d) BH3 in THF, then H₂O₂, OH- (f) Excess H₂, Pd/C catalyst (a) H₂, Lindlar catalyst (c) 1 equiv Br₂ (e) H₂O, H₂SO4, HgSO4 9.26 Identify the reagents a-c in the following scheme: = 9.24 Predict the products from reaction of 2-hexyne with the following reagents: (b) 1 equiv HBr (a) 2 equiv Br₂ (c) Excess HBr (d) Li in NH3 (e) H₂O, H₂SO4, HgSO4divls depends oin the moisture content of the reaction mixture. Propose a detailed mechanism for ench of the following steps to account for the observed The outeome of oxidation of alkenes with 1odine and silver acetate to afford stereochemistry of the product HO () 2, 2 RCO2Ag (i1) NaOH (aq) HO HO () 2, RCO2Ag, H20 (11) NaOH (aq) HO
- An inexperienced graduate student treated dec-5-ene with borane in THF, placed the flask in a refrigerator, and left for aparty. When he returned from the party, he discovered that the refrigerator was broken and that it had gotten quite warminside. Although all the THF had evaporated from the flask, he treated the residue with basic hydrogen peroxide. Tohis surprise, he recovered a fair yield of decan-1-ol. Use a mechanism to show how this reaction might have occurred.(Hint: The addition of BH3 is reversible.)*8Chemistry 60. Give the principal product(s) expected, if any, when trans-1,3-pentadiene reacts under the following conditions. Assume one equivalent of each reagent reacts unless noted otherwise. (a) H2O, H3O+ (b) Na+EtO- in EtOH (c) Maleic anhydride heat19. (a) Show the structure of all reactants and products for the bromination of 1,2 dimethylcyclopentene. Show the proper stereochemistry of the products. 1,2-dimethylcyclopentene + Br2/CCl4-----> Products (b) Show the mechanism of the reaction in (a) above.