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онHow do I get from the first compound to the second one? It should only take about 2-3 steps.

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Answer #1

The compound 2 can be prepared from compound 1 by Grignard reaction followed by oxidation as shown below

он EtMgBr (excess) KMnO4 он - ОН

The mechanism is as follows.

OMOBI ) OO EtMgBr OMgBr EtMgBr OMOBI EtMgBr I V I H30+ HON BrMgo Ue LOH OH EtMgBros y PMgBr BrMgo V oMaBr BrMgO MgBr Oxidatio

Excessive Grignard addition of Ethyl Magnesium bromide will attack all the lactone carbonyl two times to form two tertiary alcohols. Also, one secondary as well as one primary alcohol will be formed in the molecule. Under oxidation conditions, primary alcohol will be converted into carboxylic acid group and secondary alcohols will be converted into ketone. Tertiary alcohols will be unaffected under the oxidation conditions.

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