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For each of the single, pure compounds given to the right, provide a name. Be sure to designate R/S and E/Z when necessary


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There are only four constitutional isomers with molecular formula C4H9NO2 that contain a nitro group (–NO2). Three of these isomers have similar pKa values, while the fourth isomer has a much higher pKa value. Draw all four isomers and identify which one has the higher pKa. Explain your choice. 

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Consider the following reaction:

(k) Will the rate be affected by an increase in temperature?

 

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Consider the following reaction:

(j) How will the rate be affected if the concentration of hydroxide is doubled?

 

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Consider the following reaction:

(i) Is the reaction first order or second order?

 

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Consider the following reaction:

(h) Is the transition state closer in structure to the reactants or products? Explain.

 

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Consider the following reaction:

(g) Draw the transition state of this process, and identify its location on the energy diagram.

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Consider the following reaction:

(f) Would you expect an increase in temperature to have a significant impact on the position of equilibrium (equilibrium concentrations)? Explain.

 

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Consider the following reaction:

(e) Is ΔG for this process positive or negative?

 

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Consider the following reaction:

(d) Would you expect ΔSsys for this process to be positive, negative, or approximately zero?

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Consider the following reaction:

(c) Would you expect this process to be exothermic or endothermic? Explain.

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Consider the following reaction:

(b) Identify the two characteristic arrow-pushing patterns that are required for this mechanism.

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Consider the following reaction:

(a) Draw the curved arrows showing a mechanism for this process.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

 

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

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Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

 

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Under basic conditions (catalytic MeO in MeOH), compound 1 rearranges through the mechanistic sequence shown below to a propellane-type isomer 5 (J. Am. Chem. Soc. 2012, 134, 17877– 17880). Note that MeO– is catalytic in that it is consumed in the first step of the mechanism and regenerated in the final step. Provide curved arrows consistent with each mechanistic step and the resonance structure of 2 that is the greatest contributor to the resonance hybrid.

 

 

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Draw curved arrows for each step of the following mechanism:

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Compound has been prepared and studied to investigate a novel type of intramolecular elimination mechanism (J. Org. Chem. 200772, 793–798). The proposed mechanistic pathway for this transformation is presented below. Complete the mechanism by drawing curved arrows consistent with the change in bonding in each step. 

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Indolizomycin is a potent antibiotic agent produced by a microorganism called SK2-52. Of particular interest is the fact that SK2-52 is a mutant microorganism that was created in a laboratory from two different strains, Streptomyces teryimanensis and Streptomyces grisline, neither of which is antibiotic producing. This raises the possibility of using mutant microorganisms as factories for producing novel structures with a variety of medicinal properties. During S. J. Danishefsky’s synthesis of racemic indolizomycin, compound was treated with triphenylphosphine (PPh3) to afford compound (J. Am. Chem. Soc. 1990112, 2003–2005). The reaction between and then gave compound 4. These processes are believed to proceed via the following intermediates. Complete the mechanism by drawing all curved arrows and identify the arrow-pushing pattern employed in each step. 

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Draw curved arrows for each step of the following mechanism:

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