Chapter 11, Problem 40CP

Interpretation Introduction

Interpretation:

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

Concept Introduction:

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.

Bromination: olefin reacts with bromine to give bromo alkanes.

Meta-chloroperoxybenzoic acid ($\text{m-CPBA}$): This reagent is extremely useful reagent most frequently encountered in the synthesis of epoxides when added to alkenes or alkynes.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base.  Similarly it can be protected by using $\text{TMSCl}$ in presence of base.

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.