5. Draw mechanisms for the following transformations. Show all intermediates and indicate the flow of electrons with the appropriate arrows. OH HO HO- но OCH3 HO OCH3 CH3Q OCH3 Ph H Ph p-TSOH HO- HO OCH3 OCH3 Досно Ха OCH3 HO- p-TSOH CH3O OCH3 CH3O OCH3

All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.

Come up with a detailed mechanism for the following cyclization that also includes all resonance strictures for any intermediates that form. Also, explain why the alkyl bromide portion of the molecule remains intact in the product even though the reaction conditions are strongly basic/nucleophilic. Br Br NaOMe Me Me Me Me MeOH MeO2C 0 °C MeO₂C

Only the red section needs to be completed

Which set of starting materials could be used to prepare the following compound in one step? * Meo -CHO Meo сно CO,Me MeO Meo .CO,Me Meo Meo CO,Me CO,Me Meo. CO,Me Meo CO,Me RCO,H Meo `cO,Me Meo CO,Me

Each of the following transformations is believed to proceed by a sequence of reactions concerted. Indicate what happens at each step. a) -соосн b) hv CH,0OCC=CCOOHCH, COOCH3 HO. םי'ו H. CH CH3 CH3. CH3 CH3, CH3 300°C CH3- 300°C "CH3 c) CH3- D D hu H. H

7. Give a Mechanism for the following reaction; show formal charges and significant intermediates. e CH3CH₂NH2 H3O+ N CH₂CH3 + H₂O

Optically pure R 2-bromopentane reacted with Nal in acetone to give optically pure S-2-lodopentane. The rate of this reaction was found to depend on the concentrations of both 2-bromopentane and Nal. Propose a mechanism for this reaction. Be sure to show the flow of electrons structure of any reactive intermediates and the transition state of the reaction. H Br Nal acetone

Complete the reaction map by matching A-E with the given choices. H2 H2 B E Pt Cla Na in lig NH3 он + но Match each item to a choice A

Provide the reagents needed to perform the (a)-(g) conversions. Some reactions may require more than one step, so you may need to provide more than one reagent. Он CH3 CH3 b) HO c) d) f) el но OCH3