Arrange the following in decreasing order of boiling point.
(i) `CH_(3)CH_(2)CH_(2)CH_(2)OH` (ii) `CH_(3)CH_(2)OCH_(2)CH_(3)`
(iii) `CH_(3)CH_(2)CH_(2)COOH`

Explanation

Due to much stronger H-bonds in carboxylic acids than in alcohols, the boilig points of carboxylic acids are much higher than the boiling points of the corresponding alcohols. However, due to absence of H-bonding in ethers, the boiling points of ethers are much lower than alcohols and carboxylic acids of cojmparable molecular masses. thus, the boiling decreases in the order:
`CH_(3)CH_(2)CH_(2)COOH gt CH_(3) CH_(2)CH_(2)CH_(2)OH gt CH_(3)CH_(2)OCH_(2) CH_(3)`.