--%>

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 : What is ortho effect? Orthosubstituted

    Orthosubstituted anilines are generally weaker bases than aniline irrespective of the electron releasing or electron withdrawing nature of the substituent. This is known as ortho effect and may probably be due to combined electronic and steric factors.The overall basic strength of ort

  • Q : Calculating value of molar solution

    Choose the right answer from following. An X molal solution of a compound in benzene has mole fraction of solute equal to 0.2. The value of X is: (a)14 (b) 3.2 (c) 4 (d) 2

  • Q : Explain the mechanism of Enzyme

    A mechanism for enzyme-catalyzed reactions that leads to the typical rate equation for these reactions can be described.A variety of rate equations are required to portray the rates of enzymes catalyzed reagents and physical conditions that are encountered

  • Q : Molal elevation constant of water The

    The boiling point of 0.1 molal aqueous solution of urea is 100.18oC  at 1 atm. The molal elevation constant of water is: (a) 1.8    (b) 0.18   (c) 18    (d) 18.6Answer: (a) Kb

  • Q : Problem on bubble point The following

    The following mixture of hydrocarbons is obtained as one stream in a petroleum refinery.

    Q : Coordination compounds discuss the

    discuss the practical uses of coordination compounds, give reactions involves and explain whats happening in the process

  • Q : Moles of chloride ion Select the right

    Select the right answer of the question. A solution of CaCl2 is 0.5 mol litre , then the moles of chloride ion in 500ml will be : (a) 0.25 (b) 0.50 (c) 0.75 (d)1.00

  • Q : Molarity of Nacl solution When 5.85 g

    When 5.85 g of NaCl (having molecular weight 58.5) is dissolved in water and the solution is prepared to 0.5 litres, the molarity of the solution is: (i) 0.2 (ii) 0.4 (iii) 1.0 (iv) 0.1

  • Q : Chemists have not created a periodic

    Explain the reason behind that the chemists have not created a periodic table of compounds?

  • Q : Biodegradable polymers what are the

    what are the examples of biodegradable polymers