Compound A and compound B both have molecular formula C6H12. Both compound produce epoxides when treated...

Compound A and compound B both have molecular formula C₆H₁₂. Both compound produce epoxides when treated with MCPBA. The epoxide resulting from compound A was treated with aqueous acid (H₃O⁺) and the resulting diol has no chirality centers. Propose two possible structures for compound A. The epoxide resulting from compound B was treated with (H₃O⁺) and the resulting diol was a meso compound. Draw the structure of compound B.

Solutions

Expert Solution

The given molecular formula is C₆H₁₄

So there is one double bond in the given compounds (A and B) as both are giving epoxides on treatment with m-CPBA.

a) The epoxide resulting from compound A was treated with aqueous acid (H₃O⁺) and the resulting diol has no chirality centers: It means that the compound has no chiral centre (carbon with four different functional groups).

b)The epoxide resulting from compound B was treated with (H₃O⁺) and the resulting diol was a meso compound.

queen_honey_blossom answered 2 years ago

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