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1) Consider respect the to following substitution reactions and associated rate data and discuss increase the rate mechanism and two that (i.e. would analyze decrease the data). it for Also, each propose reaction. two solvents briefly that would SPh2 Nu Nu + SPh2 Ph = Phenyl Rate of reaction (105 k, St1) of nucleophiles (Nu) with PhCH,StPh Nucleophile: AcO Cr PhO HO PhS Rate: 3.9 4.0 3.8 74 107 Nu CH3Br CH3Nu Relative rates of reaction (water = 1) of nucleophiles (Nu) with MeBr: Nucleophile: AcO CI PhO HO PhS Rate: 900 1100 2000 1.2x104 5x107 2) Provide mechanistic rationale for the following two transformations and discuss. CI CI MeOH O CI O OMe OH HCl CI O 3) of dimethyl sulfate. product(s), Please any, provide mechanistic rationale, including movement Predict the if when phenol is treated with sodium hydroxide in of the electrons presence and resonance structures (note: none of these compounds are solvents). OH KOH (MeO)2SO2 4) Which reaction is best suited for the preparation of the following ether: (CH3)SCOCH2CH3 (B)CH3CH2MgBr+(CH3)3COH (C) CH3CH2Br + (CH3)3COK (D) (CH3)3CMgBr + CH3CH2OH or water, using arrow pushing, indicate the mechanism by which this common intermediate 5) Both of these amines undergo a similar reaction in either the presence of sodium hydroxide forms and draw its structure. In determining the structure of this intermediate, consider the chemistry he structures of the two products, consider the reactivity of sodium hydroxide and water and the of the functional groups on these molecules and how they might react. In determining substitution reaction mechanisms that they each promote. Draw of each product, and discuss. a mechanism for the formation Me N(Et)2 (Et)2N CI CI Me Similar intermediate NaOH, H2O Product 1 Product 2 6) Please provide the product(s), if any, of the following reactions. If there is more than one product, indicate which will be major and which will be minor. Also, using mechanistic rationale, discuss the relative rates of reaction of these two sube tituted cyclohexanes. NaOPr NaOPr Br

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Organic Chemistry Questions
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