Answer all parts of the question please. ง 6) The compound provided below was found to occur via an SN1 mechanism in the presence of a strong nucleophile NASH which have a high electron density. You are required to justify this mechanistic approach based on several potential stabilizing factors in the structure. You are to clearly show hybridization orbitals, electron-pushing arrows to signify any stabilizing factor. Add lone pairs when applicable.

Please answer part b and c

3. An alkene can be converted into an ether in the three mechanistic steps shown below. Complete this mechanism by: Draw curved arrows to indicate the flow of electrons for each step. Lone pairs are omitted for clarity but be sure to include lone pairs on atoms that are involved in bond formation/breaking. Draw the reaction intermediates in the appropriate boxes. Include all nonzero formal charges. Classify each step of the mechanism using the boxes below each arrow as one of the following: acid- base proton transfer (AB), nucleophilic attack (NA), elimination (E), or rearrangement (R). + H-OMe H-OO + MeOH + MeOH + H-OMe H-OO 48

Rationalize the formation of compound B using the arrow-pushing formalism. Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created. H: EXP CONT Submit Request Answer Br: H UN Br 6:46 PM

Use the curved-arrow formalism to show how the electrons flow in the resonance form on the left to give the one on the right. Make the ends of your arrows specify the origin and destination of reorganizing electrons. Arrow-pushing Instructions Submit Answer m H Try Another Version 2 item attempts remaining a Use curved arrows to show how the alkene below will react with HCI. Make the ends of your arrows specify the origin and destination of reorganizing electrons. Arrow-pushing Instructions NA ↔XT H H

2. Shown below are two molecules that contain functional groups that you will study in great detail in C342 (engne and enol, see below). Each of these molecules can act as either a carbon nucleophile or a carbon electrophile. Draw all of the significant resonance structures of each of these molecules, and provide the resonance hybrid of each. Based on the partial charges on the resonance hybrid, indicate whether you would expect each to be a carbon nucleophile or carbon electrophile. a. An "enol" - means it contages an alkene "epe" next to an alcohol "gl" OH Resonance structures: Resonance hybrid: Carbon nucleophile or carbon electrophile?

Don't provide hand written solution.

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

H Select to Add Arrows H H H H H Li Ⓒ Li Ⓒ Problem 3 of 21 Please select a drawing or reagent fr

1. For the four structures provided, Please answer the following questions in the table below. a. Please draw π molecular orbital diagram (use the polygon-and-circle method if appropriate) and fill electrons in each molecular orbital b. Please indicate the number of π electrons c. Please indicate if each molecule provided is anti-aromatic, aromatic, or non- aromatic TT MO diagram Number of π e- Aromaticity Evaluation (X choose one) Non-aromatic Aromatic Anti-aromatic || ||| + IV