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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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Most popular questions from this chapter

Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

(d)

Question: Addition of HCl to 1,2-dimethylcyclohexene yields a mixture of two products. Show the stereochemistry of each, and explain why a mixture is formed.

We鈥檒l see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?

Iodine azide, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene isused, only one product results:

a) Add lone-pair electrons to the structure shown for, and draw a

second resonance form for the molecule.

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?
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