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Chapter 8: Q54b (page 262)

Question: Which of the following alcohols could notbe made selectively by hydroboration鈥搊xidation of an alkene? Explain.

Short Answer

Expert verified

Answer

Possible

Step by step solution

01

Step 1: Anti-markovnikov’s rule

In hydroboration-oxidation reaction two steps occur:

  • Hydroboration- It occurs in an anti-Markovnikov manner, where hydrogen (from BH3) attaches to the more substituted carbon and BH2to less substituted carbon in double-bonded carbon. It is syn addition which means that the hydroboration takes place on the same face of the double bond.
  • Oxidation step involves the replacement of BH2 with hydroxyl group.
02

 Step 2: Alcohol possible or not:

Given alcohol is possible when a double bond is between C2and C3 as both are equally substituted so can attach to any side. Other alcohol possible is the same as given. Thus, this alcohol is made selectively.

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