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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

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

Iodine azide,adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as1-butene isused, only one product results:

b) Calculate formal charges for the atoms in both resonance structuresyou drew for,in part (a).

When an unsymmetrical alkene such as propene is treated with N-bromosuccinimide in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Is this Markovnikov or non-Markovnikov orientation? Explain

Show the structures of alkenes that give the following products on oxidative cleavage within acidic solution:

Compound A has the formula C8H8. It reacts rapidly with KMnO4to giveCO2 and a carboxylic acid, B (C7H6O2), but reacts with only 1 molar equivalent of H2on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4 equivalents ofH2 are taken up and hydrocarbon C (C8H16)is produced. What are the structures of A, B, and C? Write the reactions.
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