a. Draw the structures of the following compounds.
(i) 1 − chloro − 5 − methyl hexan − 2 - one
(ii) 2 − (2’ − bromophenyl) ethanal
b. Account for the following statement.
The pKa value of benzoic acid is 4, while pKa value of phenol is 9.8; although both are acidic.
OR
A symmetrical compound of molecular formula C4H8, on ozonolysis, gives a compound ‘A’, which on treatment with Zn/H2O gives compound ‘B’. The products obtained on reduction and oxidation of compound ‘B’ combine to form compound ‘C’. Compound ‘B’ reacts with the next member of its homologous series in the presence of NaOH to give a mixture of different products.
Identify the compounds ‘A’ to ‘C’ and the mixture of products formed on reaction of ‘B’ with its next member. Also, write the chemical equations involved.