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assignment9answers - CHM 3120 Assignment 9 Answers 1...

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CHM 3120 Assignment 9 Answers 1. Propose a synthesis of the following. Use any alkyl halide needed. Br O O NH 2 O O NH 2 O O Br O O N 3 O O NH 2 + "N - " Retrosynthesis Synthesis NaN 3 H 2 O, acetone PPh 3 , H 2 O 2. Propose a synthesis of this CNS stimulant starting with precursors of 5 carbons or less. O CO 2 Et O O CO 2 Et Br MeNH 2 Br N O ONa CO 2 Et Na(CN)BH 3 NaOEt N H N H N H O CO 2 Et Retrosynthesis Synthesis 1) NaOH 2) H 3 O+ 3) NH 2 Me 3. Propose a synthesis of the following from compounds containing 6 carbons or less. NH O H H NH O H H CHO O H H OMe CHO CO 2 Me Retrosynthesis
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CHO CO 2 Me CHO O H H OMe NH 3 Na(CN)BH 3 NH O H H O H H OMe NH Synthesis O H H OMe NH 2 4. Propose a synthesis of the following. Ph O Ph N Ph N LiAlH 4 Ph OH Ph N O Ph O (MeO) 3 CCH 3 H + Ph O NHMeEt, Ph N O LiAlH 4 Ph N Ph O OMe Ph OMe O Ph OH Ph OMe O from Retrosynthesis 1 2 3 4 5 6 Claisen Synthesis Or 1) NaOH 2) SOCl 2 3) NHMeEt 5. Synthesize the antidepressant drug Prolithane N N O Ph CHO H N O from Retrosynthesis +
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