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Chem357_Multi_step_Syn__Last_Days___Final_

Chem357_Multi_step_Syn__Last_Days___Final_ - Multi-step...

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1 Multi-step Synthesis Multi-step Synthesis PRACTICE WITH MULTI-STEP AND SPECTRAL PROBLEMS 2 Multi-step Synthesis Multi-step Synthesis Question 1. (10 MARKS) Starting with bromocyclohexane, propose a scheme to prepare racemic trans -1,2-dimethoxycyclohexane. Br OCH 3 OCH 3
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3 Question 1. (10 MARKS) Starting with bromocyclohexane, propose a scheme to prepare racemic trans -1,2-dimethoxycyclohexane. Br OH OH OCH 3 OCH 3 RETROSYNTHETIC ANALYSIS Br OCH 3 OCH 3 Multi-step Synthesis Multi-step Synthesis 4 Multi-step Synthesis Multi-step Synthesis Question 1. (10 MARKS) Starting with bromocyclohexane, propose a scheme to prepare racemic trans -1,2-dimethoxycyclohexane. Br LDA Consider the following "potential" solution. KMnO4 COLD, HO Br OCH 3 OCH 3
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5 Question 1. (10 MARKS) Starting with bromocyclohexane, propose a scheme to prepare racemic trans -1,2-dimethoxycyclohexane. Br LDA OH OH Consider the following "potential" solution. KMnO4 COLD, HO Br OCH 3 OCH 3 Multi-step Synthesis Multi-step Synthesis 6 Multi-step Synthesis Multi-step Synthesis Br LDA mCPBA O H + H 2 O OH OH OCH 3
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