Chapter 11, Problem 39CP

Interpretation Introduction

Interpretation:

A synthesis of this compound using acetylene as only source of carbon atoms has to be proposed.

Concept Introduction:

Markovnikov addition: The addition reaction of parotic acids to a different alkene or alkyne, the hydrogen atom of $\text{H-X}$ becomes bonded to the carbon atom that the greatest number of hydrogen atoms in the starting alkene or alkyne.

Anti-Markovnikov’s addition: The unsymmetrical alkene in a chemical compound reacts with hydrogen halide in a way, where halide ions attacks and bond to the less substitution position of carbon-carbon double bond.

Lindlar reduction: The alkenes or alkynes can be reduced to alkanes with ${\text{H}}_{\text{2}}$ in the presence of metal catalyst $\left(\text{Pd}\right)$. 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.

Soda amide (${\text{NaNH}}_{\text{2}}$): The strong base of ${\text{NaNH}}_{\text{2}}$ will deprotonate alkynes, alcohols and other organic functional groups with acidic protons such as asters and ketones.  It is also a very strong nucleophile. It is a strong base and excellent nucleophile.  It’s used deprotonated of weak acids and also for elimination reaction.

${\text{S}}_{\text{N}}2$Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration. Rate of ${\text{S}}_{\text{N}}2$ reaction depends on both alkyl halide and the nucleophile present.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$