Question

Choose a plausible synthesis for the following transformation, from the options below. Write the entire sequence by showing aPlease include an explanation

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Answer #1

None of the four Options won't give our product. In option 4 instead of EtMgBr, if we have used MeMgBr we will get the product as shown below.NaOH > OH + Natco 2. 014 at PCC - oxidation Kadoo aldehyde Mechanism 03 OH tla-Cr-o I 2. P. CC

H OH proton transfer

Omg BV o Me - Mg Br Hof Cr-olu. OH Mq Br + chromic acid Chromic and is prepared from Naz Con Og Hero and H2o Na, Cr₂ g + H₂O

Option 1 and option 3 are same. In it, H20 in 4th step will lead to an alcohol(not our product).

Option 2 H3O+ in step one will be acted nowhere in the molecule. And even if it is able to remove Cl- from the molecule, the final product will be a alcohol.

So we are left with option 4(with modification: replacing Et by Me in EtMgBr.

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