Write out the mechanism (intermediate/transition state) for this reaction; Br CH3 NaOCH, Ę₂ For the following use ONLY reactions we have studied in class. Check your notes or the Powerpoint slides for preparations and reactions of relevant functional groups a) Write out 6 completely different reactions of cyclohexanone (reagent, product). b) Write out 3 preparations of 2-butanol, using a different starting material for each one. You may use preps where you just change the functional group, and/or preps where you construct the carbon chain. c) Write out 3 preparations of 4-phenylbutanoic acid, a different starting material for each one. You may use preps where you just change the functional group, and/or preps where you construct the carbon chain.

12B. CARBONYL REACTION MECHANISMS Draw the arrow-pushing mechanism for the reactions, including all charged intermediates and product. Mix & Match (Mechanism Bootcamp): draw the mechanism for each starting material (1-6) and reagent from the 12B reactions (previous page) (1a) NABH4 MeOH

Br bromobenzene 1) Mg, Et₂O 2) (acetone) HO. 2-phenyl-2-propanol please show the COMPLETE mechanism! Thank you.

HW 10 #7

H* CH3OH H2O H. OCH3 ÕH 4-hydroxypentanal reacts with one equivalent of methanol to form a cyclic acetal. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions H-A :A H3C" H3C" Submit Answer Try Another Version 1 item attempt remaining 11:32 PM O 57% 4/11/2021

Identify one of the major products for each of the reactions. Be sure to include all relevant sterochemistry using wedges and dashes. No mechanism necessary

hw10 #7 help on part 3

Propose a sequence of reactions that efficiently converts the given starting material(s) to the target molecule. Draw the structure of the product formed after each synthetic step. Do not write mechanisms. ntiomer 4. Propose a sequence of reactions that efficiently converts the given starting material(s) to the target molecule. Draw the structure of the product formed after each synthetic step. Do not write mechanisms. Ph + enantiomer a) Ph. Ph H 2 equiv. b) + Br