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- 2 3 5 [Review Topics] Reagents HBr a. b. C. H₂O, H₂SO4 d. Br₂ Cl₂ H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 e. f. g. h. i. j. k. I. [References] HBr, H₂O2, hv Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O2, NaOH O3 then (CH3)2S m. n. O. p. q. r. S. t. u. V. 2 equivalents of NaNH₂ H₂, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia)2BH then H₂O₂, NaOH 1 equivalent of NaNH2 NBS, hv Br₂, hv Cl₂, hv HCI Identify the reagents necessary to accomplish the following steps in the above synthesis of 3-hexanone from acetylene: Step 4: v Step 5: F Step 7: Previous Next Save and Exit1. Identify the major product? &=&&&* b Br t-BuOK OH t-BuOH a 2. The hydroxide ion (OH) in the following reaction behaves as hote Br H K a. Electrophile; b. Nucleophile; c. Acid; d. Base a. NaCN, DMSO b. t-BuOH с + C. CH3CONA, CH3OH d. TsCl A H₂O + Br 3. For the following compound identify the reagent most likely to give you an elimination product by E2 mechanism d15. Organic compound X is oxidized to 2,3-dihydroxypropionic acid. Compound X is: A. propanol, B. propanal, X + Cu(OH)₂2 →→ Cu₂O + H₂O + HO-CH₂-CH(OH)-COOH C. 1,2,3-trihydroxypropan, D. 2,3-dihydroxypropanal, E. glicerol
- Reagents m. 2 equivalents of NaNH2 H2, Lindlar's catalyst Na / NH3 p. H2SO4, HgSO4 q. (sia)2BH then H2O2, NaOH 1 equivalent of NaNH2 a. HCI b. HBr n. c. H20, H2SO4 d. Br2 0. n Cl2 е. H2, Pd g. Br2, H20 h. Cl2, H2O f. r. compound a Os04 then NaHSO3 j. Hg(OAc)2, H20 then NABH4 k. BH3 then H2O2, NaOH Oz then (CH3)2S i. compound b I. The above synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook. 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. • 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 menu.Fill in the appropriate products for the giving starting materials and reagents. Na Cr,0, H.O 1. Hg(OAc),, H,O PCC 2. NABH,9. A Select all products expected for the following reaction. A. B F. Br Br o NBS hv C G. D. M Ø