Chapter 12, Problem 66IP

Interpretation Introduction

Interpretation:

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

Concept introduction:

Lindlar’s 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.

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.

The Grignard reagent reacts with the appropriate aldehyde or ketone $\left({\text{CH}}_{\text{3}}\text{CHO}\right)\text{,}$ followed by a water workup to produce the alcohol.