Arrange the following compounds according to increasing order of boiling points. n-C4H9OH (A), n-C4H9NH2 (B), n- C4H10 (C) and C2H5NHC2H5 (D).
- C < B < A < D
- D < C < B < A
- C < D < B < A
- D < B < A < C
Answer
(3) C < D < B < A
Solution
Molar masses are close (74, 73, 58, 73 g mol-1), so boiling point is decided by intermolecular hydrogen bonding.
n- C4H10 (C): non-polar, only weak van der Waals forces ⇒ lowest
C2H5NHC2H5 (D): 2° amine, one N–H per molecule ⇒ weak H-bonding
n-C4H9NH2 (B): 1° amine, two N–H per molecule ⇒ more extensive H-bonding
n-C4H9OH (A): O is more electronegative than N ⇒ O–H···O bonds are stronger than N–H···N ⇒ highest
∴ C < D < B < A
Answer: (3)