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- Define about Sigmatropic Rearrangements ?(c) You conducted an experiment involving a hydrohalogenation reaction with starting material A and HBr. Product C was obtained as the major product of the reaction instead of the regioisomer product B which you expected. CH3 CH3 CH3 Br Br + HBr Product B Starting material A Product C (i) Suggest a detailed reaction mechanism to explain the formation of the major product C. (ii) Briefly explain why this unexpected major product C predominated in your reaction. Question 1 Continued (iii) 1,2-elimination of HBr from product C yields a mixture of two alkenes. Draw the structures of the two alkene products and briefly explain using Zaitsev's rule which alkene is the major one.A solution of pure (S)-2-iodobutane ([a] = +15.90°) in acetone is allowed to react with radioactive iodide, 131I -, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°. (a) Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.
- ㅇ (E)- (Z)- ㅇ (R)- ㅇ (S)-a) Explain the regiochemical outcome (i,e major vs minor product formation) for the following reaction: CN CN CN maj or minor b) Use molecular orbital theory to explain in detail the stereochemical outcome for the following transformation: lightConsider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)
- 2444 The following are examples of hetero Diels-Alder. Draw the mechanism and the products. (a) (b) CO2CH3 + + H3CO,CA solution of pure (S)-2-iodobutane ([a] = +15.90°) in acetone is allowed to react with radioactive iodide, 131I -, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°. (a) What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ∆H° for the following reactions. (a) CH3¬CH3 + I2 ¡ CH3CH2I + HI(b) CH3CH2Cl + HI ¡ CH3CH2I + HCl(c) (CH3)3C¬OH + HCl ¡ (CH3)3C¬Cl + H2O (d) CH3CH2CH3 + H2 ¡ CH3CH3 + CH4 (e) CH3CH2OH + HBr ¡ CH3CH2¬Br + H2O
- 6) Provide the enantiomeric Diels-Alder adducts that would form from the following reaction along with the two transition states leading to them: + HO₂CQII: Give the stereochemical outcome for each of the following reactions and assign the stereochemical relationship between the products: (1) Br, CI, KMnO,, Он, Н,о (2) Cold, dilute (3) HBr НСІ Но (4) ZnCl, PCC excess ОН (5) CH,CI, ОН(1) (ii) (iii) (iv) (v) What is the relationship between the compounds [Cl-Ag-SCN]™ and [SCN-Ag-CIJ? Name the compounds whose molecular formulae are given in Question 1(a) (i). Which of the compounds, [Cl-Ag-SCN] and [SCN-Ag-CI], is the more stable? Explain your answer. Draw the boundary surfaces of all 3d orbitals and label these orbitals according to the conventional nomenclature. Clearly draw and label the Cartesian axes. Draw the crystal field splitting diagram for a linear compound, e.g. [Cl-Ag-SCN] or [SCN-Ag-CI], aligned along the z-axis. You only need to indicate the order of the individual d orbitals as a function of the energy. Explain your answer.