Chapter 11.5, Problem 10ATS

Interpretation Introduction

Interpretation:

A synthetic route of given compounds have to be proposed.

Concept Introduction:

Anti-Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the less substitution position of carbon-carbon double bond and gives alkyl halides.

Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

  

Lindlar reduction: The alkenes or alkynes can be reduced to alkanes with ${\text{H}}_{\text{2}}$ in the presence of Lindlar’s catalyst.  This heterogeneous catalyst that consists of palladium deposited on calcium carbonate which is then poisoned with various forms of lead or Sulphur.  The new $\text{C-H σ}$ bonds are formed simultaneously from $\text{H}$ atoms absorbed into the metal surface.

Elimination Reaction: It is just reverse reaction of addition reaction where substituent from the given molecule is removed via E1 (the reaction depends only on the substrate involved in the reaction) or E2 (the reaction depends on both of the substituents in the reaction) mechanism.

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene.  Boron addition to the double bond and subsequent oxidation of the newly formed borane yields anti-Markovnikov alcohols.