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Compound A , C 11 H 16 O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B , C 11 H 14 , was the major product. Alkene B , on ozonolysis, gave two products. One product was identified as propanal, CH 3 CH 2 CHO. Compound C , the other product, was shown to be a ketone, C 8 H 8 O. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .
Organic Chemistry
Solutions
Organic Chemistry
Compound A , C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B , C11H14, was the major product. Alkene B , on ozonolysis, gave two products. One product was identified as propanal, CH3CH2CHO. Compound C , the other product, was shown to be a ketone, C8H8O. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .
Interpretation:
Given an optically active alcohol, A has the molecular formula C11H16O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene, B (C11H14). The alkene B yields propanol, CH3CH2CHO and a ketone, C (C8H8O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written.
Concept introduction:
The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced.
To calculate:
The number of degrees of unsaturation in compound A.
To identify:
The structures of compounds A, B and C.
To write:
The reactions given.
Explanation of Solution
The molecular formula of the compound A is C11H16O. The molecular formula of the corresponding parent hydrocarbon is C11H24.Thus the compound A has eight hydrogens less than the parent. Hence the degree of unsaturation in A is four. If the double bonds present in an aromatic ring are not hydrogenated in the presence of Pd. So the compound has a benzene ring which accounts for the four degrees of unsaturation. Alcohols when warmed with dilute sulfuric acid lose a molecule of water to yield an alkene...
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