--%>

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 : Forms a molecule to an organic molecule

    Briefly state what forms a molecule to an organic molecule?

  • Q : Mole fraction of water and ethanol Give

    Give me answer of this question. A solution contains 1 mole of water and 4 mole of ethanol. The mole fraction of water and ethanol will be: (a) 0.2 water + 0.8 ethanol (b) 0.4 water + 0.6 ethanol (c) 0.6 water + 0.8 ethanol (d) 0.8 water + 0.2 ethanol

  • Q : Thermodynamics I) Sulphur dioxide (SO2)

    I) Sulphur dioxide (SO2) with a volumetric flow rate 5000cm3/s at 1 bar and 1000C is mixed with a second SO2 stream flowing at 2500cm3/s at 2 bar and 200C. The process occurs at steady state. You may assume ideal gas behaviour. For SO2 take the heat capacity at constant pressure to be CP/R = 3.267

  • Q : Question on Mole fraction Mole fraction

    Mole fraction of any solution is equavalent to: (a) No. of moles of solute/ volume of solution in litter (b) no. of gram equivalent of solute/volume of solution in litters (c) no. of  moles of solute/ Mass of solvent in kg (d) no. of moles of any

  • Q : Molarity of solution Help me to go

    Help me to go through this problem. When 7.1gm Na2SO4 (molecular mass 142) dissolves in 100ml H2O , the molarity of the solution is: (a) 2.0 M (b) 1.0 M (c) 0.5 M (d) 0.05 M

  • Q : Product of HCl Zn Illustrate  the

    Illustrate  the product of HCl Zn?

  • Q : PH of an Alkyl Halide Briefly state the

    Briefly state the pH of an Alkyl Halide?

  • Q : Molarity of sodium hydroxide Can

    Can someone please help me in getting through this problem. Determine the molarity of a solution having 5g of sodium hydroxide in 250ml  solution is: (i) 0.5  (ii) 1.0  (iii) 2.0   (d) 0.1Answer: The right answer i

  • Q : Which is polar HCl or HF Which one is

    Which one is polar HCl or HF?

  • Q : Death cap musrooms the death cap

    the death cap mushroom based on your knowledge of the biochemistry of dna and rna