--%>

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 : Which is polar HCl or HF Which one is

    Which one is polar HCl or HF?

  • Q : Normality of acetic acid Give me answer

    Give me answer of this question. The normality of 10% (weight/volume) acetic acid is: (a)1 N (b)10 N (c)1.7 N (d) 0.83 N

  • Q : Procedure to judge that organic

    Describe briefly the procedure to judge that the given organic compound is pure or not?

  • Q : Define Bond Energies - Bond Charges

    Energy changes in some chemical reactions can be used to deduce the energies of chemical bonds. Our understanding of the molecular basis of thermodynamic properties is extended when we ask why the enthalpy change for a reaction is what it is. We deduce,

  • Q : Problem on vapour pressure and mole

    Provide solution of this question. The vapour pressure of a solvent decreased by 10 mm of mercury, when a non-volatile solute was added to the solvent. The mole fraction of the solute in the solution is 0.2. What should be the mole fraction of the solvent, if decrea

  • Q : Pressure Phase Diagrams The occurrence

    The occurrence of different phases of a one component system can be shown on a pressure temperature. The phases present in a one line system at various temperatures can be conveniently presented on a P- versus-T diagram. An example is pro

  • Q : Ddd 4) The addition of S2- ion to

    4) The addition of S2- ion to Fe(OH)2(s). Explain why the addition of S2- ion to Cr(OH)3(s) does not result in the formation of Cr2S3(s).

  • Q : Linde liquefaction process Liquefied

    Liquefied natural gas (LNG) is produced using a Linde liquefaction process from pure methane gas at 3 bar and 280 K (conditions at point 1 in figure below). A three-stage compressor with interceding is used to compress the methane to 100 bar (point 2). The first stage

  • Q : Explain physical properties of

    . Boiling pointsThe boiling points of monohalogen derivatives of benzene, which are all liquids, follow the orderIodo > Bromo > ChloroThe boiling points of isomeric dihalobe

  • Q : Partial vapour pressure of volatile

    Choose the right answer from following. For a solution of volatile liquids the partial vapour pressure of each component in solution is directly proportional to: (a) Molarity (b) Mole fraction (c) Molality (d) Normality