In chronological order, describe what happens at each step and where each compon

Question

In chronological order, describe what happens at each step and where each component is contained after each operation. Every step has a rationale for why it is being done, so explain this. If any changes are occurring to a particular chemical, explain what is changing and the consequence (e.g. why is the mixture extracted with aqueous NaOH?)

I especially would like help understanding the second part of this reactions flow chart. Like why do we dissolve it in hot water and gravity filter, is something otherwise insoluable and the heat helps? Why then is my unknown chilled? What does it mean if I ended up with very little of my unknown and a lot of tetraglyme? Did i not use enough water, or I didn't heat it up enough? Please help me understand. Thanks!

Explanation / Answer

in first step mixture is 4 components is dissolved in dicholormethane , since starch is insoluble in dichloromethane

it will remain as solid

in second step dichloromethane solution of 3 components is treated with aq. NaOH, here carboxylic acid react with sodium hydroxide to form sodium salt of carboxylic acid and it is highly soluble in water

therefore in aqueous layer sodium salt of carboxylic acid will be there and dichloromethane portion contain other two componenet. sodium salt of carboxylic acid and be converted in carboxylic acid by treating with conc HCl

in third step DCM solvent was evaporated

the two component mixture was dissolved in hot water, where amide is less soluble in water compare to tetraglyme

therefore under cold condition

aromatic amide will be solidified and tetraglyme will present in aqueous solution.

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