Question

A hydrocarbon with the formula $C_{10}{H}_{16}$ gives 4-methyl-3-oxopentanal and 3-oxobutanal on reductive ozonolysis. Its structure is:

• A.
• B.
• C.
• D.

Answer 1

Answer: (A), (C)

Ozonolysis of alkenes involves the addition of an ozone molecule to an alkene, to form an ozonide. Formed ozonide gets cleaved by $Zn/H_{2}O$ to smaller oxidised molecules.

Compound (a) and (c) on ozonolysis gives 4-methyl-3-oxopentanal and 3-oxobutanal as shown:


Compound (b) on ozonolysis gives 5-methyl-4-oxohexanal and 2-oxopropanal (methyl glyoxal).


Compound (d) on reductive ozonolysis gives malonaldehyde.