122. * Predict the products of the following reactions. In (a) and (d), give the intermediate resulting from the rate-determining step and explain why it is formed and controls the outcome of the reaction. c) d) e) a) b) NBS CCI4, A Cl2 heat Br₂, hv NBS CCI4, light NaN(C(CH3)2)2 A Br NaNH, Br A
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- • H2O Based on the reaction above, (a) Outline the reaction mechanism. (b) Sketch the energy diagram. (c) Give the rate equation. (d) Explain what happens to the reaction rate if: The leaving group is changed to I. (0) (a) The solvent is changed to DMF. The alkyl halide is changed to (v) The concentration of the solvent is increased by five-fold answer with proper justification and with good explanationCompound D, shown below, reacts with hydrogen bromide by electrophilic addition. A mixture of two organic compounds, E and F, is formed. CH3 CH₂CH₂ CH3 H compound D HBr Mixture of organic compounds E and F (i) Name the the two organic compounds E and F and show their condensed formula. (ii) Briefly explain the mechanism of the reaction between compound D and hydrogen bromide to form either compound E or compound F. (You can list/state the main steps) (iii) Which compound, E or F is the major product?a) propose an outline of a possible mechanism for the conversion of a to b. provide illustrations as necessary. b) provide or suggest an explanation for the regioselectivity of "b" formation. x₂ CC13 CC14 Cl3C 2 eq. MeO- C
- (b) Describe the hazards of (i) trioxygen: (ii) hydroxide ion; (ii) hydrogen sulfide. (c) Explain why an aqueous solution of sodium sulfide has an odor of hydrogen sulfide. (d) (11) Reduction of H,CCHCHO with NABH4 gives a product different from that of catalytic hydrogenation (H2 /Ni). What are the products?2. (a) The solvolysis reaction of compound 2A in acetic acid generated two major products 2B and 2C. Answer the following questions: (i) Draw the reaction mechanism for the for mation of 2B and 2C. (ii) Interestingly, researchers also observed the formation of 2D as a minor product. Propose a plausible mechanism to explain the formation of 2D. LOTS CH3COOH LOAC LOAC + AcO 2A 2B 20 2D (minor)4b)Give the mechanisms for the following:
- Answer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrows9) A student described the following reaction as "I brominated it then added bulky base with heat". . A What would the different products be for the following different brominating reagents? NBS, Br₂, HBr, HBY/ROORdivls 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