Problems

Explain the following observed phenomena

1. Cyclohexanone does not exist in its hydrated form but 1,3-diphenylpropane-1,2,3-trione does.
   
   
2. Glyoxal when treated with a strong solution of sodium hydroxide resulted in glyoxallate anion.
   
   
3. When the reaction given above is carried out in heavy water, insertion of deuterium in the
   methylene group of the product is not observed.
   
   
4. Mg turnings when treated with a solution of mercury(II) chloride in acetone results in formation of pinacol.
   
   
5. The pinacol formed in the above reaction when treated with dilute sulphuric acid results in a compound which gives a orange precipitate with 2,4-dinitrophenyl hydrazine.
   
   
6. Pinacolone when treated with an aqueous solution of bromine in sodium hydroxide, pivalic acid is formed.
   
   
7. When methyl acetate is heated in pure ethanol containing a small amount of HCl catalyst, ethyl acetate results.
   
   
8. 1-Chloro-3-phenylpropan-2-one when treated with base results in 3-phenylpropanoic acid.
   
   
9. Diethylsuccinate reacts with mesityl oxide in the presence of a base to give dimedone.

 

Text Books

 

•  P. Y. Bruce and K J R. Prasad, Essential Organic Chemistry , Pearson Education, New Delhi, 2008.

•  C. M. Loudon , Organic Chemistry , Oxford University Press, New Delhi, 2002.

•  R. R. Morrison, R. N. Boyd and S. K. Bhattacharjee, Organic Chemistry , Dorling Kindersley (India) Pvt. Ltd, New Delhi, 2011.