Chapter 15: Q60. (page 570)

Question: Devise a synthesis of each compound using CH3CH3 as the only source of carbon atoms. You may use any other required organic or inorganic reagents.
a.
b.
c.
d.

Short Answer

Expert verified

Answer

Step by step solution

Organic synthesis

Organic synthesis is the strategic reactions and transformations of organic compounds that are readily available to form desired products through new covalent bond formations.

Devising Synthesis of the given compounds

a. Ethane is chlorinated to give ethyl chloride that is treated with alcoholic potassium hydroxide solution to form ethene. Ethene is treated with bromine in carbon tetrachloride to form 1,2-Dibromoethene that undergoes dehalogenation with alcoholic potassium hydroxide to form ethyne.

Ethane to ethyl chloride

Formation of ethene

Formation of ethyne

e. A molecule of ethane is transformed to ethene using chlorine, followed by an alcoholic base. The ethene reacts with bromine and undergoes dehalogenation to form ethyne. Ethyne is deprotonated using a strong base sodium amide and treated with 2-Iodoethanol to form But-3-yne-1-ol.

Formation of ethyne from ethane

Formation of But-3-yne-1-ol

f. Ethane is chlorinated to ethyl chloride that undergoes dehalogenation using alcoholic potassium hydroxide to give ethene. Ethene undergoes oligomerization in the presence of the Ni catalyst to form the required Hex-3-ene.

Formation of ethene

Formation of Hex-3-ene

g. Ethane is converted to ethene by chlorination, followed by dehalogenation using alcoholic KOH. Ethene undergoes oligomerization to form Hex-3-ene that hydrated using sulphuric acid to form Hex-3-ol. This is oxidized using potassium dichromate to form the required ketone.