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Give the expected major product of reaction of 2,2-dimethyloxacyclopropane with each of the following reagents.

Give the expected major product of reaction of 2,2-dimethyloxacyclopropane with each of the following reagents. (d) concentrated HBr (a) dilute H2SO4 in CH30H (e) CH3Mgl, then H /H20 (b) NaOCH3 in CH30H (f) C6H5Li, then H*/H20 (c) Dilute aqueous HBr

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Answer #1

In presence of acids, nucleophile opens the epoxide at more substituted carbon. In presence of bases, nucleophile opens the e

Both methyl magnesium bromide and phenyl lithium are strong bases. So, they open the epoxide at less substituted carbon. (e)

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