Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. سلام xylenes, 110 °C

1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3

4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3

The accepted mechanism for a rearrangement reaction is shown below. "Q Ph (1) (ii) Ph Ph HO™ fast Ph Ph HO O™ slow Ph aufae .Ar² LOH HO™ fast Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. HQ Ph (iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining. Ph (iv) Write the predicted rate equation for this mechanism, and show how it was derived. (v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃ labelling experiment that would allow you to distinguish which of the two aryl groups had migrated in this situation. OH AR²0- Ar¹ C C

2) reaction sequences to carry out those transformations. Draw the expected product of each step proposed. Substantial partial credit can be obtained for incomplete or incorrect answers. You may present your solutions on the following blank page if you need the the following reaction transformations, and propose room. H3C CH, H3C CH3 of HN- -NH HO,C Co,H но H,C CH3 CEN OCH3 OCH3

Under acid-catalyzed conditions, epoxides can be opened by a variety of nucleophiles other than water, such as alcohols. In such a case, the nucleophile will generally attack at the more substituted position. Using this information, predict the products for each of the following reactions (a-b): ? 1) RCO-H 2) [H₂SOJ Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. CH₂ Edit Drawing A

(b) Show the mechanism of this reaction using proper arrow push notation. You must show all intermediates, formal charges, and necessary arrows. CH3 CH3 CH3 H20 H2SO4

Mechanism 2. Provide the complete mechanism for the reactions below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. OH H2SO4 (cat) THF OH

(d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + Br

a and b