a. .14. Predict the major product of the following reaction sequence. منا. Br OH 1. CH3OH, H3O+ 2. NaOCH 3. NaOH 4. H3O+ OH منذ للام OH ? لللا e. سلام

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The below synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook. compound a m compound b q Reagents a. HCI b. HBr c. H₂O, H₂SO4 d. Br2 Cl₂ H₂, Pd compound c e. f. g. h. i. j. Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 k. I. m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst O. p. Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S In this synthesis, reagents from the table (shown in blue) are used to carry out the indicated reactions. In the box below, draw the structure of compound b. q. r. Na/NH3 H₂SO4, HgSO4 (sia)₂BH then H₂O₂, NaOH 1 equivalent of NaNH2 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Consider E/Z stereochemistry of alkenes. ● If more than one structure fits the description, draw them all. ● If a compound is formed more than once, add another sketcher and draw it again. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down…

Predict the major product for the following reaction. A. مسلم مة في ملية کی B. E. NaOH/H₂O A C.

4. There are six steps in the mechanism below. Identify the basic moves in this complicat ed mechanism – one we will see next semester when we discuss carbonyl compounds. The point is that even complicated mechanisms can be broken down into simple terms and movements we recognize from the beginning of organic chemistry. Н. Н A. но B. н но он D. Он E. H. Н F. :o: Он

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Choose the reagents that can be used to perform the following transformation: Select one: a. "OH, H₂O ...OH e. OH b. H3O+ X c. Na₂Cr₂O7, H₂SO4 d. KMnO4, OH Both -OH, H₂O and H3O+ (separately) will work.

Select reagents from the following table to bring about this conversion. a. HOCH₂ CH₂ OH, H+ 1. Os04 2. NaHSO3 RCO3 H H3O+ NaBH₁ b. (Enter your result as a string of letters, in the order that you wish to use the reagents, i.e. ade.) C. d. e. LOH f. g. HO dihydropyran, H+ 1. BH3 2. NaOH, H₂O, H2₂ O2 OH

5. Propose a synthesis of each of the following compounds using the indicated starting material. You may use any organic compounds, inorganic compounds, organometallic compounds, or solvents of your choice. Do not show any reactive intermediates, mechanisms, or transition states, but be sure to show each isolable compound along your synthetic route. a. b. C. Ph + PPh3 Cl mylom Ph. CH3 steps steps steps H3C. H3C Ph CH3 CH3 Ph OH ÕH Ph (racemic) 4

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