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Chapter 8: Q54d (page 262)

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

Short Answer

Expert verified

Answer

Not 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

Alcohol possible or not

Given alcohol is not possible as hydrogen is attached to less substituted carbon. Thus, this alcohol can’t be made selectively.

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Most popular questions from this chapter

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

What products would you obtain from catalytic hydrogenation of the following alkenes?

Question: What product would you expect to obtain from addition of to 1,2-dimethyl-cyclohexene? Show the stereochemistry of the product.

An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts withOsO4 to give diol B. When oxidized withKMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.

Hydroxylation of cis-2-butene with OsO4yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.
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