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3 . ) ( 1 0 pt ) Write a step - wise mechanism for the following transformation. Show electron flow with appropriate arrows. ?

3.)(10 pt) Write a step-wise mechanism for the following transformation. Show electron flow with appropriate arrows.
?CH3OHNaOCH3
4.)(10 pt.) Reaction of compound A, formula C8H14O, with the Wittig reagent CH2=P(C6H5)3 produces compound B,C9H16. Treatment of compound A with LiAlH4 yields two diastereomeric products C and D, both C8H16O, in unequal yields. Heating either C or D with concentrated sulfuric acid produces compound E, with the formula CsH14. Ozonolysis of E produces a keto aldehyde. Oxidation of this keto aldehyde with chromic acid produces:
Provide structures for compounds A through E. Pay particular attention to the stereochemistry.
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