4. Using curved arrows, draw a reaction mechanism and predict the products. Lewis Acid-Base Reaction a) :N + Bronsted Acid-Base Reaction b) + AICI3

Rank the molecules in decreasing (strongest to weakest) acidity. Include ALL resonance structures with arrows and explain reasoning for rank.

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

6. Clearly label the Lewis acid and Lewis base in each reaction. Fill in all lone pair electrons on the reactants and products, and use curved arrows to show the mechanism of the reaction. Identify formal charges on the product(s), if not already noted. 4.x-x H st H-A-H H CH, CI fo -H AIH₂ MgBr

Rank the structures from most acidic (1) to least acidic (3). A B с A =C-H [Choose ] [Choose ] [Choose ] H H H < H I

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