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.

Curved arrows are used to illustrate the flow of electrons. Using the provided resonance structures, draw the curved electron- pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond- breaking and bond-making steps. I I I I :O: f

3. What type of bond cleavage (homolytic or heterolytic) would you expect the following bonds to undergo? Write the bond cleavage process using the curved arrow convention for each.   Show the step-by-step process. Do not use shortcut methods. Make it as detailed as it can be. Encode (not hand-written)!

This structure has a lower pKa than usual because the conjugate base of the structure has unusual stability. Using the provided resonance structures, draw the curved electron-pushing arrows to show the deprotonation step. Then, draw the curved electron-pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond-breaking and bond-making steps

Please answer part b and c

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

eq eq M M M ereg 2req 2req 2req X 2req J F3 $ 4 R C V [Review Topics] [References] Draw both resonance structures of the anion formed by the reaction of the most acidic C-H bond of the compound below with base. 4x Include all valence lone pairs in your answer. • For structures having different hydrogens of comparable acidity, assume that the reaction occurs at the less-substituted carbon. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. ✓✓99.81 O 0- F4 . % 5 T G B F5 *** ^ 6 Cengage Learning Cengage Technical Support Y ChemDoodle H N F6 & N& 7 U O J F7 + [ ] در M 8 PrtScn K F8 9 Home O 83°F Sunny F9 L ) 0 End F10 P Previous C PgUp F11 9 ? Next Save and Exit 9:38 AM 7/18/2022 PgDn F12 0 Ins D Back

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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?

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