Assignment _4 answer key - Chem 3600 - Homework assignment...

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Unformatted text preview: Chem 3600 - Homework assignment #4 (Chapter 17) Due Date: Monday, 03/15/2010 The following problems in Chapter 17 of the textbook are also required: 9—19, 21-23, 25-26, 28-32, 34, 35, 38-42, 44, 46, 47, 48a, 49-51, 53, 54, 56, 59, 60, 62-65, 67, 69, 70, 75-77, 81, 84. You do notneed to turn them in, however. 1. Give the product of the followin reactions: 0 1./\MgBr I” o I.» B ‘9 Cl 2 HO+ -\ @OH ____M9_r_» 014501—15 -+ @031 . 3 N 2. H3O+ ._\ H O 1 /\ ' p 1 NaBH4 o’CH3 N’CH“ 4——> No reactioh 2. H30+ C, H 2- H30+.. O o O ' 0 K NH l.L1AlH4. / AH _ O,CH3 1.DIBALH,-78 c . H 2. H20 ' 2" ' 2.}130+ g ' ‘ , Q H301 E? :3 ° AN” [:5 + H7. dam/“"12 We“? S H 0 O ' 1 l. /\ CH3SH Q 0 \ MgBr 2. The reduction of acyclic imide by LiAlH4 often leads to cleavage, for example: 0 MfiiNJLM M n M e e z 6 5h 2.H20 P“ V Propose a mec ism for this reaction. /d—\\ H o X ‘5 H~ATH§ ($339“ ' ,1 0" 9 Am} ole/4w Me 'T’h e M {J H' 4 “a MAN}; 4' G’s/KP! > MXEN P h 3. Provide a plausible mechanism for the following acid-promoted transformations: 4. List the following ketones in order. of decreasing reactivity in nucleophilic addition reactions and explain why: » O 0 o a 0' 0 WWW" MAW” “Mei-"944$ “alum Mflle ("twain 9 (1-20" —-> 1075" ) which «:3 Mag—art- 1)“ Ewmme/V y.‘mj 5. Achieve the following syntheses using the specified starting materials in fewer than 5 steps. Feel free to use any other reagents you need. C02 / '_>, / H50+ O xLH‘i’j‘VI—l‘l O ...
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Assignment _4 answer key - Chem 3600 - Homework assignment...

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