Orgo Question

[jaz129]

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What happens if you have react an aledehyde with NABH4 , then with ethelyne oxide(with HA) ?

I know that NaBH4 reduces aldehydes to alcohols but what will ethelyne oxide do?
Thanks

 

[passDAThope]

What happens if you have react an aledehyde with NABH4 , then with ethelyne oxide(with HA) ?

I know that NaBH4 reduces aldehydes to alcohols but what will ethelyne oxide do?
Thanks

Isn't the HA with a with a primary alcohol just an SN2 reaction? I believe that the A- will replace the OH- like in a simple SN2 rection.

 

[jaz129]

This was a question on my orgo2 midterm, but I thought it was relevant. I just looked over the answer and the aldehyde is reduced to the alcohol(propanal=>proponol). THen with the addition of the ethyloxide/HA it becomes this:

CH3-CH2-CH2-O-CH2-CH2-OH, btw how would u name this?

Except I don't know how? I don't knw by what mechanism this occurs?

 

[jaz129]

So I spoke to my prof. and he told me that after the aldehyde is reduced to the propanol it acts like a nucheophile and opens up the epoxide, in an SN2 like reaction. So if the ring where unsymmetrical the propanol would add to the least substituted Carbon atom.

Thanks for the input