--%>

Describe properties of carboxylic acids.

1. Physical state: the first three aliphatic acids are colourless liquids with pungent smell. The next six are oily liquids with an odour of rancid butter while the higher members are colourless, odourless waxy solids. Benzoic acid is referred to as crystalline solid.


2. Solubility the first four aliphatic members are soluble in water due to intermolecular hydrogen bonding with water molecules.

With increasing size of alkyl groups, the non-polar part of the molecule predominates thereby reducing the solubility in water. The higher members are almost insoluble in water.

3. Boiling points: carboxylic acids have quite high boiling points due to presence of intermolecular hydrogen bonding which results in the formation of dimeric structures. 

Due to dimeric structure, the effective molecular mass of the acid becomes double the actual mass. Hence, carboxylic acids have higher boiling points than alcohols of comparable molecular masses. Moreover, O-H bond in carboxylic acids is more polar than O-H bond in alcohols. This is due to electron withdrawing effect of carbonyl group on O-H. Hence, H-bonds in carboxylic acids are comparatively stronger than those of that in alcohols.

4. Melting points: in first ten members of homologous series, the alternation effect is observed. The alternation effect implies that the melting point of an acid with even number of carbon atom is higher than the acid with odd number of carbon atoms above and below it. However, no such effect is observed in homologues with more than ten carbons. The alternation effect can be explained on the basis of the fact that the carboxylic acids with even number of carbon atoms, the terminal methyl group and carboxyl group of the opposite sides of zig-zag carbon chain. Hence, they fit better in the crystal lattice and it results in stronger intermolecular forces. On the other hand, acids with odd number of C atoms have carboxyl and terminal methyl number of C atoms has carboxyl and terminal methyl groups on the same side of zig-zag carbon chain. Therefore, such molecules being relatively unsymmetrical, fit poorly in the crystal lattice. This causes weaker intermolecular forces and accounts for the relatively lower melting points.
268_carboxylic acid.png 
Even number of C-atoms, fit better, in crystal lattice, have higher m.pts (Terminal groups are on opposite side)
2096_carboxylic acid1.png 
Odd numbers of C-atoms, fit properly, in crystal lattice, have lower m.pts. (Terminal groups are on same side).    

The melting and boiling points of aromatic acids are generally higher than those of aliphatic acids of similar molecular masses. This is presumably due to the fact that planar benzene ring in these acids can pack closely in the crystal lattice than zig-zag aliphatic acids.

   Related Questions in Chemistry

  • Q : How much phosphorus is in superphosphate

    Superphosphate has the formulate: CaH4 (PO4)2 H2O calculate the percentage of Phosphorus in this chemical. Show your calculations

  • Q : Molecular Properties Symmetry Molecular

    Molecular orbitals and molecular motions belong to certain symmetry species of the point group of the molecule.Examples of the special ways in which vectors or functions can be affected by symmetry operations are illustrated here. All wave functions soluti

  • Q : What is Distillation Separation by

    Separation by distillation can be described with a boiling point diagram. The important process of distillation can now be investigated. From the boiling point diagram one can see that if a small amount of vapour were removed from a liquid of composit

  • Q : What are Vander Waal's Radii? Vander

    Vander Waal's radii can be assigned to the atoms of molecules on the basis of the closeness of approach of these atoms in crystalline substances. Diffraction studies of crystals give information about hoe molecules can approach each other and can pack

  • Q : How reactive is Trimethylindium towards

    Illustrate the reason, how reactive is Trimethylindium towards oxygen and water?

  • Q : What is protein in Chemistry Illustrate

    Illustrate what is protein in Chemistry?

  • Q : Question based on vapour pressure and

    Benzene and toluene form nearly ideal solutions. At 20°C, the vapour pressure of benzene is 75 torr and that of toluene is 22 torr. The parial vapour pressure of benzene at 20°C for a solution containing 78g of benzene and 46g of toluene in torr is: (a) 50 (b)

  • Q : Vapour pressure related question Help

    Help me to solve this question. Which of the following is incorrect: (a) Relative lowering of vapour pressure is independent (b)The vapour pressure is a colligative property (c)Vapour pressure of a solution is lower than the vapour pressure of the solvent (d)The

  • Q : Finding Normality Can someone please

    Can someone please help me in getting through this problem. Concentrated H2SO4 has a density of 1.98 gm/ml and is 98% H2SO4 by weight. The normality is: (a) 2 N  (b) 19.8 N  (c) 39.6 N  (d) 98

  • Q : Solubility are halides are halogens

    are halides are halogens more soluble? why?