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- Which of the following provides a synthetic route to convert 3-iodo-2-methyl-1- butene into 2-methyl-2-butene? 1. NaOH; 2. H₂, Pt 1. H₂, Pt; 2. Br2 1. H₂, Pt; 2. NaOEt 1. H₂, Ni₂B; 2. KOtBu 1. H₂, Pt; 2. KOtBuselect reagents: cyclopentanone Reagents a. C6H5CHO b. NaOH, ethanol c. Pyrrolidine, cat. Hj. d. H₂C=CHCN e. H3O+ f. LDA g. A) bg EtOC(=O)CO₂Et h. i. B) ka k. I. m. O: BrCH₂CH=CH₂ NatOEt, ethanol Br₂, H+ K+ t-BUO™ CH2(CO2Et)z heat C) jh CO₂Et D) Imi. 3-methyl-1-butene with HBr CH3 H,C=CH-CH-CH3 Major Product(s) of i. j. 2-methylbut-1-ene + Br2 in CH3OH CH3 H2C=CH-CH2-CH3 Major Product(s) of j.
- 3 Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example. Starting Materials Ex. b. C. d. dj f. 09 ỌCH3 CH3 CH3 NO₂ Reagents H₂O H* (cat.) C1₂ AICI3 HNO3 H₂SO4 SO3 H₂SO4 Br₂ FeBr3 AICI3 Major Product(s) O= OH4. Provide the missing reagent(s) and major product(s) for the following reactions. a. a.ii. b. НО. A + B a.i. H₂SO4 (conc.), A pyridine a.iii. HO a.iv. CI OH A B4. Identify the diene and dienophile used to make these Diel-Alder products. b. CH3 CN deo & CH3 a. CO₂CH3 CO₂CH3
- From the table of reagents shown below, show how you synthesize the product from the given reactant. Br Reagents available a. NBS, (PhCO2)2 h. CH3 Cl, AIC13 CUCN 0. b. Br2, FeBr3 i. CH3 CH2 Br р. НзО*, д с. Вг2, Н+ j. CH3O¯, A q. CH; CH2 COCI, AICI3 r. k. CH3 COCI, AICI3 H2NNH2, OH, A d. OH- e. NaOH(s), A 1. Mg, Et20 s. H2, Pd/C f. HNO3, H,SO4 m. CO2(s) then H3O+ t. H3PO2 g. H2 CrO4 n. HONO 0°C u. Cl2, FeCl3 (Enter the letter(s) of the reagent(s) needed in the box, in the order that they must be used. No more than two steps are required to perform the synthesis. Note that a retrosynthetic arrow is used, and therefore the reactant is shown on the right.) Answer:Which starting material produces the two products shown after ozonolysis and a reductive workup? 1. O3 2. DMS C. А. D. В. A.6. Provide the structure for the major product in the following reactions. b. P f. OH g. Lia * Oia ملی CI 1. SOCI₂, pyr. 2. to Br 2 1. LIAIH4 (xs) 2. H₂O 1. LIAI(OR) 3H 2. H₂O 2. NH₂ Et₂CuLi 1. EtMgBr (xs) 2. H₂O 1. Mg 2. CO₂ 3. H* 4. SOCI₂, pyr 1. [H], NaBH3CN, EtNH₂ CI pyridine

