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When the alkyl bromides (listed here) were subjected to hydrolysis in a mixture of ethanol and water (80% EtOH/20% H2O) at 55°C, the rates of the reaction showed the following order:
(CH3)3CBr ˃ CH3Br ˃ CH3CH2Br ˃ (CH3)2CHBr
Provide an explanation for this order of reactivity.
 

 

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When tert-butyl bromide undergoes SN1 hydrolysis, adding a “common ion” (e.g., NaBr) to the aqueous solution has no effect on the rate. On the other hand, when (C6H5)2CHBr undergoes SN1 hydrolysis, adding NaBr retards the reaction. Given that the (C6H5)2CH+ cation is known to be much more stable than the (CH3)3C+ cation (and we shall see why in Section 15.12A), provide an explanation for the different behavior of the two compounds.
 

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Give structures for the products of each of the following reactions:
 

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Give structures for the products of each of the following reactions:
 

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Give structures for the products of each of the following reactions:
 

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Give structures for the products of each of the following reactions:
 

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Give structures for the products of each of the following reactions:
 

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When ethyl bromide reacts with potassium cyanide in methanol, the major product is CH3CH2CN. Some CH3CH2NC is formed as well, however. Write Lewis structures for the cyanide ion and for both products and provide a mechanistic explanation of the course of the reaction.
 

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1-Bromobicyclo[2.2.1]heptane is extremely unreactive in either SN2 or SN1 reactions. Provide explanations for this behavior.
 

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(b) Consider the opposite problem, that of carrying out a substitution reaction on a tertiary alkyl halide. Use as your example the conversion of tert-butyl chloride to tert-butyl ethyl ether. What experimental conditions would you employ to ensure the highest possible yield of the ether?
 

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(a) Consider the general problem of converting a tertiary alkyl halide to an alkene, for example, the conversion of tert-butyl chloride to 2-methylpropene. What experimental conditions would you choose to ensure that elimination is favored over substitution?
 

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Explain the following observations: When tert-butyl bromide is treated with sodium methoxide in a mixture of methanol and water, the rate of formation of tert-butyl alcohol and tert-butyl methyl ether does not change appreciably as the concentration of sodium methoxide is increased. However, increasing the concentration of sodium methoxide causes a marked increase in the rate at which tert-butyl bromide disappears from the mixture.
 

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Many SN2 reactions of alkyl chlorides and alkyl bromides are catalyzed by the addition of sodium or potassium iodide. For example, the hydrolysis of methyl bromide takes place much faster in the presence of sodium iodide. Explain.

 

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Draw a three-dimensional representation for the transition state structure in the S N2 reaction of N=C:- (cyanide anion) with bromoethane, showing all nonbonding electron pairs and full or partial charges.
 

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Write mechanisms that account for the products of the following reactions:
 

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Write mechanisms that account for the products of the following reactions:
 

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Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (h) CH3CO2- (-OAc) or OH -


 

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Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (g) H2S or HS-

 

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Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (e) H2O or H3O+

 

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Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (b) CH3O- or CH3CO2- (-OAc)

 

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Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (a) CH3NH- or CH3NH2


 

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Consider the reaction of I - with CH3CH2Cl, (e) If [I -] = 0.2 mol L-1 and [CH3CH2Cl] = 0.2 mol L-1?

 

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Consider the reaction of I - with CH3CH2Cl. (d) If [I -] = 0.2 mol L-1 and [CH3CH2Cl] = 0.1 mol L-1?

 

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Consider the reaction of I - with CH3CH2Cl. (c) If [I -] = 0.1 mol L -1 and [CH3CH2Cl] = 0.2 mol L-1?

 

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Consider the reaction of I - with CH3CH2Cl.(b) What is the reaction rate if [I -] = 0.1 mol L-1 and [CH3CH2Cl] = 0.1 mol L-1?

 

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