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  •  » Methanol/sulfuric acid opening of 3-methyl-2,3-epoxypentane

#1 2009-02-23 18:08:13


Methanol/sulfuric acid opening of 3-methyl-2,3-epoxypentane

Yahoo!Answers in chemistry wrote:

Draw the major organic product when (2S,3R)-3-methyl-2,3-epoxypentane reacts with methanol in the presence of sulfuric acid.

This reaction is crosses over between SN1 and SN2 properties. The opening of the epoxide will lead to attack at the more stable carbocation (if it formed). This is SN1-like. The nucleophile attacks from the opposite side of the leaving OH, an SN2-like attack. The chirality of C2 is preserved while that at C3 is inverted.



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