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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter9: Addition Via Cyclic Intermediate

Section: Chapter Questions

Problem 2E

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In the following problems, design a realistic method for the synthesis of 2 products in the reaction from the specified
starting (reactant) molecule. Assume that simple inorganic and organic reagents, and suitable solvents, are readily
available, but they must be specified.
C.
OH
d.
OH

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In the following problems, design a realistic method for the synthesis of 2 products in the reaction from the specified starting (reactant) molecule. Assume that simple inorganic and organic reagents, and suitable solvents, are readily available, but they must be specified. a. O b. ол d. C. صد Br O OH NO2
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Given the reaction; determine the reagents needed a.) H30) and catalytic Hg(-2) b.) (1) BH3 in THF and (2) H2O2 and aqueous NaOH c.) KMNO4 in aqueous NaOH d.) (1) HO-Br and (2) aqueous NaOH
5. Complete textbook problems covered in class by drawing the products to the right of each reaction arrow. Assume the presence of excess acid or base and halogen. [3 pts each] a. Cl2 H2O, HCI b. 12, ΟΗ C. I2, OH d. Br2 CH3CO₂H
1. Reaction of excess methyllithium with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___. 2. Reaction of excess ethyl magnesium bromide with ethyl benzoate (C6H5CO2C2H5) produces, after acid work-up, ___. 3. Reaction of excess ethyl magnesium iodide with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___.
3/ Which of the following reactions will take place? Justify your answer. d. e. NH₂ CH3CH₂CI+ CH3O¯ f. ~ + NH₂ CH3CH₂OCH3 + CI F JOHF - O + OH
In each reaction box, place the best reagent and conditions from the list. 1) CEN 2) 3) 4) 5) Answer Bank NANH, NaBH, acetone CH,CH, MgBr (excess) acetic acid acetate ion CH,OH, H,O* (cat.) LIAIH, (CH,),CHMgBr (excess) CH,MgBr (excess) H,0 H,0*, H,0, heat acetyl chloride
6. Provide reagents and intermediates in the indicated boxes to complete the reaction scheme. + H NaBH3CN, HCI (two steps, no acidic hydrolysis, from one product) 016H (w/o heat) 1. MeLi (xs) 2. HCI, H₂O NH₂ 1. Saponification 2. A 0 1. MeMgBr (xs) 2. HCI, H₂O 018 Me NH₂ 1. Dibal H, 2. H3O+ POCk3, pyr or + 1. LIAIH(O'Bu)3 (XS) 2. acidic workup
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