9.9. Reaction of 3,5,5-trimethylcyclohex-2-en-1-one with NaNH₂ (3 equiv) in THF generates an enolate. When bromobenzene is added to this solution and stirred for 4 h, a product 9-A is isolated in 30% yield. Formulate a mechanism for this reaction. CH3 CH3 HO 9-A CH3

A chemist hoped to make an ethyl ester using diazoethane. At the end of the reaction, only the original carboxylic acid, ethene, and nitrogen were produced: □ CH H EXP 0+ H₂C OH Suggest an arrow-pushing mechanism that accounts for these products. 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. L CONT. 1 H₂C O NEN: OH ΝΕΝ OH *O* + H₂C=CH₂ + N₂ H с N O S CI Br I

Nitesh

c) t Mechanism d) NH₂ Mechanism + H₂S + Csl CH3CH₂OH DMSO