--%>

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 : Colligative properties give atleast two

    give atleast two application of following colligative properties

  • Q : Base parachloroaniline is strong base

    parachloroaniline is strong base than paranitroaniline

  • Q : What is depression in freezing point?

    Freezing point of a substance is the temperature at which solid and liquid phases of the substance coexist. It is defined as the temperature at which its solid and liquid phases have the same vapour pressure. The freezing point o

  • Q : Theory of three dimensional motion

    Partition function; that the translational energy of 1 mol of molecules is 3/2 RT will come as no surprise. But the calculation of this result further illustrates the use of quantized states and the partition function to obtain macroscopic properties. The partition fu

  • Q : Short note on the function of

    Write down a short note on the function of mitochondria?

  • Q : Problem on physical and thermodynamic

    The shells of marine organisms contain calcium carbonate CaCO3, largely in a crystalline form known as calcite. There is a second crystalline form of calcium carbonate known as aragonite. Physical and thermodynamic properties of calcite and aragonite at 298

  • Q : Kinds of insulators Describe all the

    Describe all the kinds of insulators which are present?

  • Q : Problem on Neutralization What weight

    What weight of hydrated oxalic acid should be added for complete neutralisation of 100 ml of 0.2N - NaOH solution? (a) 0.45 g  (b)0.90 g  (c) 1.08 g  (d) 1.26 g      Answer

  • Q : DNA Organic Explain DNA organic in

    Explain DNA organic in brief?

  • Q : Problem on vapour pressure Choose the

    Choose the right answer from following. If P and P are the vapour pressure of a solvent and its solution respectively N1 and N2 and are the mole fractions of the solvent and solute respectively, then correct relation is: (a) P= PoN1 (b) P= Po N2 (c)P0= N2 (d)