4. An alcoholic compound was found to have molecular mass of 90 u. It was acetylated. Molecular
mass of the acetyl derivative was found to be 174 u. How many alcoholic (-OH) groups must be
present in the original compound?
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lAcetylation of an alcohol takes place in the following manner:
R−OH
→
Acetylation
R−OAc
Thus, it is clear that each −OH group is replaced by a −OAc group. Now, the weight of an acetyl group (Ac) is 43 and the weight of the lost Hydrogen atom is 1. Upon completion of reaction, for each −OH group present in a molecule, there is an increase of 43−1=42 units of weight.
Now, net increase in weight of the given molecule (390−180)=210
Thus, total number of −OH groups in the original molecule is
42
210
=5
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