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Q.

Choose the appropriate reagent sequence from the given reagent pool to complete the synthetic conversion. Make sure to use strictly four reagents, not more not less.
Note: You can simply mention the numerical values corresponding to the reagent in the boxes P, Q, R and S respectively and also consider major organic product in each step. What is the value of [P + R + S – Q]?
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1.  HBr                                 2. H+/H2O                      3. Hg(OAc)2H2O                4.  BH3.THF
5. EtONa/EtOH/Δ       6. HBr/ROOR/Δ         7.  conc.H2SO4/Δ             8. NaBH4 

9. H2O2,aq.NaOH         10. tBuOK/Δ

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Detailed Solution

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Chemical Reaction Explanation

The image shows a chemical reaction involving the conversion of an alkene into an alcohol. Here's the explanation:

  1. Starting Material:

    The reactant is a branched alkene with a double bond between the terminal carbon and the adjacent carbon.

  2. Reagents:
    • HBr/ROOR/Δ: This step likely introduces a bromine atom to the less substituted carbon of the double bond (anti-Markovnikov addition of HBr).
    • t-BuOK/Δ: This strong base induces elimination (E2 mechanism) to regenerate a terminal alkene.
    • BH₃·THF: Hydroboration adds boron to the less substituted carbon and hydrogen to the more substituted carbon in a syn-addition manner.
    • H₂O₂/aq. NaOH: Oxidation of the boron intermediate replaces the boron with a hydroxyl (-OH) group, forming an alcohol.
  3. Product:

    The final product is a secondary alcohol located on a branched alkane, indicating anti-Markovnikov addition of water across the initial double bond.

This sequence of reactions effectively transforms the starting alkene into a terminal alcohol through a combination of hydroboration and oxidation.

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