K Problem 9.b of 28 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting structures, draw the curved electron-pushing arrows for a nucleophilic addition reaction to the carbonyl and draw the resulting intermediate. Be sure to account for all bond- breaking and bond-making steps. :0: 'H ONU CH3 Select to Add Arrows Nu: Select to Draw Product

material 15. Draw a detailed arrow-pushing mechanism for the following t FeBry Bra -Br: + FeBr Sa. Generation of The Electrophile Electrphilic Addition to form Arenium (show the resonance forms of

choose the best reagents to complete the reaction shown below

. Base . The imol 1. The forme e. Bas perfo In 1 Orav cta 1. Steric hindrance is the unfavorable electron-electron repulsion that results when bonds are forced too close to each other. a. Draw the SN2 mechanism using curved arrows for the reaction of bromoethane with Nu:-. siz b. Draw the SN2 mechanism using curved arrows for the reaction of 2-bromopropane with Nu:. vtisizvod c. Given that steric hindrance is unfavorable, predict whether the SN2 reaction of bromoethane or 2- bromopropane would be faster. d. Determine in general the order of reactivity of all alkyl halides in an SN2 reaction (methyl, 1º, etc.)

5. Draw the mechanism arrows for each of the reactions below. (8pts) NaNH2 a. b. C. CI .Cl I NaCN Base Catalyzed Keto-Enol Tautomerization H3O+ HO H₂N CI CN CN H

Lout line a synthesis tor geherating Compand ma as the excusive using Compounds Fan 6. LDA or as your Selečtish ofbases major priduct You may ust only Number es sential Steps as requiree trans farmation the Componnd

Draw the mechanism ffrom benzaldehyde to this using:   i)NaBH4 ii)TsCl, py iii)NaCN iiii)H+, H2O

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2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. b. CN Br Br CH₂ Revised F F

Draw the major product of this reaction. Ignore inorganic byproducts. 1. LDA, -78 °C 2. PHCH2BR (1 equiv) Select to Draw