A student proposes this reaction as part of a synthesis: о NaOH O OH Does this happen? If so, draw the complete mechanism below. If this transformation does not happen as written reagents or catalysts missing just check the box under the drawing area. To save you time, the starting material has been copied into the first drawing area. - for example, if there are important organic Add/Remove step × 5

1a) Provide the mechanism of the reaction below, catalyzed by triethylamine.The reaction should take you three mechanistic steps. Referring to the C=O group that already exists in the starting molecule: b) If this ketone were not present (for example, if it were just an H there instead), would the first step be faster or slower? Briefly explain. c) If this ketone were not present (for example, if it were just an H there instead), would the second step be faster or slower? Briefly explain. d) If 9.21 g of the starting reactant is used and 0.27 g of triethylamine are used, approximately how many reactions will each molecule of triethylamine catalyze? (hint: balance the equation)

-CH3 HBr -Br =CH₂ CH3 Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions NA :Br: ► ×™ -CH3 -CH3 C-CH3 H

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