HW 8KEY - 2 CH 3 2. H 3 O + 1. NaBH 4 , CH 3 OH 2. H 3 O +...

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CH 318N Spring 2008 Name: 1 Homework # 8 - KEY Due: THURSDAY 04-10-08 Please follow the HW Guidelines as posted on Blackboard. 1. Rank the following molecules in increasing order of reactivity toward addition of a nucleophile (1=least reactive, 4=most reactive) and explain your reasoning. __ 2 __ __ 1 __ __ 3 __ __ 4 __ O H O O H O O 2 N NO 2 O 2 N H 3 CO H 3 CO
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CH 318N Spring 2008 Name: 2 2. Predict the major organic products of the following reactions or indicate no reaction . Include stereochemistry where relevant using dashes and wedges. Write “+ enantiomer” if a racemic mixture is formed. O H 2 , Pd HOCH 2 CH 2 OH, H 3 O + CH 3 NH 2 1. LiAlH 4 , 2. H 3 O + H 2 NNH 2 , H 2 O KOH, (HOCH 2 CH 2 ) 2 O, heat (C 6 H 5 ) 3 P=CHCH 3 H 3 C H O O O O N H CH 3 OH (+ Z-isomer)
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CH 318N Spring 2008 Name: 3 3. Based on what you have learned in this class, suggest efficient reagents for the following transformations. More than one step may be required. O N HO OH NC O OH O OH NH 2 OH, H 3 O + (C 6 H 5 ) 3 P=CHCH 3 1. BrMgCH
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Unformatted text preview: 2 CH 3 2. H 3 O + 1. NaBH 4 , CH 3 OH 2. H 3 O + CF 3 COOH, CH 2 Cl 2 O HCN, KCN CH 318N Spring 2008 Name: 4 4. Synthesize the following compounds from benzene and any other necessary reagents. Multiple steps will be required. a) b) N O AlCl 3 , CH 3 COCl N H H 3 O + N O AlCl 3 , CH 3 CH 2 COCl (C 6 H 5 ) 3 P=C(CH 3 ) 2 CH 318N Spring 2008 Name: 5 5. Predict the major organic product and give a detailed, stepwise mechanism for the following sequence of reactions. (+ Z-isomer) Br 1. (C 6 H 5 ) 3 P, C 6 H 6 2. CH 3 CH 2 CHO H P Br (C 6 H 5 ) 3 P Br H (C 6 H 5 ) 3 P O H H O (C 6 H 5 ) 3 P H O (C 6 H 5 ) 3 P H (C 6 H 5 )P O CH 318N Spring 2008 Name: 6 Recommended Problems Chapter 17 Exercises: 1-17 (all) Chapter 17 Problems: 20, 21, 24-28 (all), 30, 31, 32, 37-44 (all), 47-50...
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HW 8KEY - 2 CH 3 2. H 3 O + 1. NaBH 4 , CH 3 OH 2. H 3 O +...

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