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Chapter 8: Q54c (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

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

 Step 2: Alcohol possible or not:

Given alcohol is not possible to synthesize from the hydroboration-oxidation reaction. Here the hydrogen and hydroxyl groups are not in the same phase. Thus, this alcohol can鈥檛 be made selectively.

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Most popular questions from this chapter

From what alkenes might the following alcohols have been prepared?

b)

Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with only 1 molar equivalent of H2. Compound A also reacts with ozone, followed by zinc treatment, to yield a symmetrical diketone, B(C10H16O2).

Write the reactions.

Question: One problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products. What are their likely structures?

Question: In planning the synthesis of one compound from another, it鈥檚 just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Which of the reactions below would result in a product mixture thatwould rotate plane-polarized light?

a)
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