Chapter 18 HW

Chapter 18 HW - 5 M NaOH Ph OAc Ph OAc Ph OH Ph OH Ph OH Ph...

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Chemistry 52 Chapter 18 Problem Set 1. Predict the major organic product of each of the following reactions. If no appreciable reaction is expected, write NR. O O CO 2 H OH CO 2 H H CO 2 H CH 2 N 2 O OH O HO Cl a) b) c) d) e) f) g) 1) MeMgBr 2) dil. HCl 1) SOCl 2 2) (CH 2 =CH) 2 Cd 1) CH 3 CH 2 CH 2 NH 2 DCC 2) LiAlH 4 3) dil. HCl Br 2 cat. P 1) mCPBA 2) LiAlH 4 3) dil. HCl 1) CrO 3 2) NaHCO 3 ,
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2. Suggest reagents and conditions to selectively accomplish the following conversions. NH 2 Br Br CO 2 H OH O O O O NH 2 O Br H O HO O O NH 2 O N H O CO 2 Me OH OH O a) b) c) d) e) f) g)
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3. Propose a reasonable synthesis for the anti-inflammatory drug Fenclorac from benzene and any other precursors. O OH Cl Cl 4. Devise a preparation of each of the following compounds using H 2 18 O as the only source of 18 O. Ph OMe 18 O Ph 18 OMe O Ph 18 OMe 18 O a) b) c) 5. Propose a mechanistic explanation for the following observations.
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Unformatted text preview: 5 M NaOH Ph OAc Ph OAc Ph OH Ph OH Ph OH Ph OH optically active dilute NaOH optically active optically inactive optically active dilute NaOH optically active optically inactive 6. Propose reasonable and detailed mechanisms for the following transformations. O O Ph O CO 2 Me CO 2 Me LiMe 2 Cu CO 2 Me O HO OH OH a) b) 1) NaHSO 4 , H 2 O 2) LiOH, H 2 O PhCO 2 Li + 7. Propose reasonable and efficient syntheses for each of the following compounds from precursors containing six or fewer carbons. O OMe OMe O O N H O HN NH O O N a) b) c) d)...
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Chapter 18 HW - 5 M NaOH Ph OAc Ph OAc Ph OH Ph OH Ph OH Ph...

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