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1. Draw the majar product far the following :-eactions involving Grignard reagents. -1.~MgBr a. -----► b. o ~H 1 · pi-(""MgBr -----► 1. CH3CH2MgBr (excess) c. -------► d. ~MgBr o 1.~H ... e. pi,-/'sr f. g. 1. Mg 2. CH3COCH3 ► 1. 2 Mg 2. CH3C02CH3 ► 1. Mg 2 ethylere oxíde ► -:, For each of the follow'ing. draw a Grignard reagent and a carbonyl compound (formaldehyde. an aldehyde. a ketone, oran ester) from ,vhich lhe alcohol shown would be produced. following acid workup. OH ex. ~ ( C/° BrM~ a. OH ~ < b. PHO~ h'LJ < c. d. e < There are two possible combinations far this one. Draw both possible combinations of carbonyl compound and Grignard. OH ~<--~-- Ph There are three possible combinations far this one. Draw all possible combinations of carbonyl compound and Grignard. OH ~ < Ph Makes this one using an ester as your carbonyl compound < rhae 'lfe \\" ~oluu ,e:; but g ,.-:! at kJ-.t ine Combo One Combo Two Combo One Combo Two Combo Three a. b. 3. Drav,• the mechanisms for the following Grignard reactions. o ~H o ~CH3 1. CH3MgBr ----► OH ~ 1. CH3MgBr (excess) OH ~ Note: Anything inside of brackets [ ] represents something that isn't or can't be isolated. Often something in brackets is an intermediate on the way to something else, and something which forros very briefly but is then carried on to product or returns back to starting material. Often something in brackets is something that never builds up, but is only present in a small equilibrium concentration. l. Draw the.mechanism for acid-catalyzed hydrolysis of the following enol. "enol" [6 ~,~ l H20, H+ 6º 2. Draw the mechanism for base-catalyzed hydrolysis of the following enol. [ 60H] H20, NaOH 6º "enol" ~ 3. Draw the mechanism for the reaction shown. O NaCN ✓H HCI OH ~CN H 2 4. Shown below is an example of a hydrate/k:etone equilibrium. Draw the mechanism for the elimination reaction (A ➔ B). 5. Fact: The conversion from A ➔ B strongly favors the carbonyl product B. But A and B are actually in equilibrium, with a small equilibrium quantity of A present (in the presence of acid and water). Problem: Draw the mechanism for the addition reaction B ➔ A. [ OH l W, H20 Ph+OH - A (A ➔ B) o Ph~ B 6. Shown below is an example of the reaction for making a ketone from a nitrile using Grignard addition followed by an aqueous acid workup/hydrolysis. Draw the mechanism for the addition phase of the hydrolysis (C ➔ D). 7. Draw the mechanism for the elimination phase ofthe hydrolysis (D ➔ E). c~N 1. CH3MgBr J) w l NH j H+ [ NH2 ] H+ Ph..... -- - )l - )l_ -- + A 2. W . H20 Ph CH3 H O Ph CH3 H O Ph CH3 H20 8 2 C 2 OH "imine" o "aminol" E C ➔ D 3 8. Draw the product for the reaction shown. 9. Draw the mechanism for formation of the product. O 1-~MgBr PhA 2. H30+ 10. Shown below is an example of the reaction for reacting aldehydes or ketones with ZNH2 compounds. Draw the final product C for the reaction shown. 11. Draw the mechanism for the addition phase ofthe reaction (A ➔ B). 12. Draw the mechanism for the elimination phase ofthe reaction (B ➔ C). 13. Fact: The conversion from B ➔ C strong ly favors the final product D. But C and B are actually in equilibrium, with a small equilibrium quantity of B present (in the presence of acid and water) . Problem: Draw the mechanism for the addition reaction C ➔ B. 14. Fact: The conversion from A ➔ B strongly favors the carbonyl reactant A. But A and B are actually in equilibrium, with a small equilibrium quantity of B present (in the presence of acid and amine). Problem: Draw the mechanism for the elimination reaction B ➔ A. o Phjl___ A B ➔ A OH Ph+ HNI B "aminol" Final Product e "imine" 4 15. Shown below is an example of the reaction for reacting aldehydes or ketones with alcohols. Draw the final product C for the reaction shown. 16. Draw the mechanism for the addition phase of the reaction (A ➔ B). 17. Draw the mechanism for the substitution phase of the reaction (B ➔ C). 18. Draw the mechanism for the reverse substitution phase of the reaction (C ➔ B). 19. Draw the mechanism for the elimination reaction B ➔ A. Fact: Bis in two equilibria, an unfavorable one with A (carbonyl strongly favored), anda solvent dependent one with acetal C. In excess alcohol, things end up at C; in water they go back to A. o ~OH OH ~OH Ph)lH Ph+H H+ -- Final Product A H+ º1 H20 e H+ B ("Acetal") "hemiacetal" A ➔ B B ➔ C 20. Shown below is base-catalyzed addition of water to form a hydrate. Draw the mechanism for the addition phase of the reaction (A ➔ B). 21. Draw the mechanism for the base-catalyzed elimination reaction B ➔ A. [folH B (hydrate)

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