organic 11 12 BUN*Ⓡ* Finish attempt ... 9 10 13 14 Question 1 Not yet answered Flag question Match each set of structures to its place in the synthesis of cyclohexanone oxime from cyclohexanone. The reagents are not balanced and water as a solvent is not include! Interestingly, amines (nitrogen containing compounds like alkaloids, e.g., cocaine, heroine, nicotine, etc.) are often sold as hydrochloride salts because amines readily react with carbon dioxide reversibly forming carbamates (another environmental problem). So in essence we are "freebasing" hydroxylamine hydrochloride like we did caffeine in the first semester. C1- *H₂N-OH H HO OH НО. H НО. H₂N-OH HO `N Nx H OH H H₂O 0 C 0 Nat Cl H₂O Na Cl Nat C1- H₂O 0=C=0 *Na O 0 C 0 H₂O HO Na C1- Na Cl 0 C 0 OH ONa+ Choose... Choose... Choose... Choose... Choose... Choose... 4 Andrea Salas Rivera AS ◆

Could you show the mechanism for Question 3, parts A-C?

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Predict the products of the following reaction. No reaction is a possible answer. 1) CH;CH,MgBr a. 2) H20 1) x.s. CgH5MgBr CI b. 2) H20 OH 1) LIAIH[OC(CH;)3]3 C. C 2) H20 OCH3 1) (CH;CH,CH,),CuLi d. 2) H2O 1) Mg in diethyl ether Br 2) CO2 3) H20 e. 1) (CH,-CH),CuLi 2) H20 f. 1) CH,CH,CH,MgBr 2) H20 g. 1) DIBAL-H 2) H20

From the table of available reagents select the one(s) you would use to convert 2-phenylethanol to each of the following products phenylacetic acid (PHCH,CO,H)| styrene (PHCH-CH,) Use the minimum number of steps; in no case are more than two steps necessary. List reagents by letter in the order that they are used, example: fa. Reagents available a. CrO3, H20, H2SO, d. O3; then Zn, CH3CO2H g. POCI3, pyridine b. Hg(OAc)2, H2O; then NaBH4 e. PBr3 h. H2, Pd c. KMNO4, H2O f. Dess-Martin Periodinane

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0 ment/takeCovalentActivity.do?locator assignment-take [Review Topics] [References] Draw structural formulas for the alkoxide ion and the alkyl(aryl) bromide that may be used in a Williamson synthesis of the ether shown. CH3 CH₂-O-CCH₂CH3 CH3 • You do not have to consider stereochemistry. . Do not include counter-ions, e.g., Na+, I, in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. . Separate structures with + signs from the drop-down menu. 99.8 Sn [F ▾ Previous Next> 3 F4 Bi % 5 T ChemDoodleⓇ Cengage Learning Cengage Technical Support F5 F6 F7 A 6 Y & 7 U * 8 [J] PrtScn F8 73°F Sunny Home 9 F9 O End 0 F10 P 4x PgUp F11 Save and Exit 8:13 AM 6/20/2022 PgDn 11 * F12 5

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