Epoxide Synthesis Question!
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Epoxide Synthesis Question!

[From: ] [author: ] [Date: 12-02-27] [Hit: ]
Addition of H+ would protonate the O- to form an alcohol. Then you would use PCC to oxidize the alcohol into an aldehyde.PhCH2Br (1.PhCH2MgBr (1. Oxirane 2.PhCH2CH2CH2OH (1.......
Heres the problem: http://tinypic.com/r/a59306/5

I'm stuck with the first step. I have no idea what reagent to use and the structure it will become.

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The first step requires a Grignard reaction. So the reagent would be an Mg/ether solution. The Grignard reagent would then attack the ethylene oxide (oxirane) and open the epoxide. Addition of H+ would protonate the O- to form an alcohol. Then you would use PCC to oxidize the alcohol into an aldehyde.

It's hard to write the synthesis here but it should look something like this:

PhCH2Br (1. Mg/ether) > PhCH2MgBr
PhCH2MgBr (1. Oxirane 2. H+) > PhCH2CH2CH2OH
PhCH2CH2CH2OH (1. PCC) > PhCH2CH2CH=O
1
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