Prob 1. Write chemical reactions to effect the following transformation.

            (a)  Butan-1-ol to butanoic acid

            (b)  Benzyl alcohol to phenylacetic acid

            (c)  Bromobenzene to benzoic acid

            (d)  p-methylacetophenone to benzene-1, 4-dicarboxylic acid






Prob 2. Arrange the following compounds in increasing order of their boiling points:

            acetic acid, methyl formate, acetamide, propan-1-ol


Sol.      (i)  Out of all these compounds methyl formate does not undergo H-bonding therefore, its boiling point is the lowest.

(ii)   Amongst the remaining three compounds intramolecular H-bonding is most extensive in acetamide, followed by acetic acid and least in propan-1-ol. Therefore, their boiling points decrease in the same order i.e. acetamide > acetic acid > propan-1-ol. Thus, the overall increasing order of their boiling points is methyl formate < propan-1-ol
< acetic acid < acetamide.

Prob 3.


Prob 4. A dicarboxylic acid (A), C4H6O4, gave a compound (B), C6H10O4 upon treatment with excess of methanol and a trace of H2SO4. Subsequent treatment of (B) with LiAlH4 followed by usual work up gave C, C4H10­O2. Heating of A yielded D, C4H4O3. Assign structures to A, B, C and D. 



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