3. What should be removed from the reactive media for the reaction below to obtain high conversion? n H3C-O-C- A. Ethylene glycol B. Methanol C. Ethanol D. Dimethyl ester of terephthalic acid CH3 + n HO–CH2CH2OH + 2л CH3OH

22. Write the structure(s) of the product(s) for each of the reactions below. a. b. C. 1. NBS, CC14 2. KOC(CH3)3, HOC(CH3)3 H₂O H₂SO4 HBr ether

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.

b. an SN1 process C. an E2 process d. an SN2 process 25. Consider the Grignard reaction below to answer the following question(s). The nucleophile in this reaction is: A MgBr H₂C 0 || B CH3 C 1. ether 2. H30* D HO Ċ---CH3 CH3

9. Provide the reagent A necessary to carry out the following conversion. Br & NH₂ Br ستر A. I A. H₂PO₂ B. HCN C. H₂O D. CH₂OH, heat 10. What is the product in the following reaction? Br -NH₂ NaNO₂/HCI < 5°C Br Br G CI Br B. II C. III NaNO₂/HCI < 5°C Br II N₂CI Br Br D. None of them LOCH3 Br E. NaOCH3 Br NO₂ Br

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2. Which one is acid catalyzed intermediate in hydration of acetone? Acid catalyzed HO OH HO A. I B. II Hydration OH || C. III D. IV H H ||| None IV

12. Draw the structure of the major organic product(s) for the following reactions and name the reaction. CH3 N-CH3 CI CH3 heat a. (name of reaction) 0- N-CH3 CI CH3 b. (name of reaction) -NH2 + CH3CH2Cl c. (name of reaction) heat NaOH 2 H d. name of reaction H3C e. name of reaction CH3 1. EtQ Na+ 2. H2O, HCI

What are the correct reaction conditions for the following transformation?