--%>

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 : Explain Rotational Vibrational Spectra

    The infrared spectrum of gas samples shows the effect of rotational-energy changes along with the vibrational energy change.As we know from the interpretations given to thermodynamic properties of gases, gas molecules are simultaneously rotating and vibrating. It follows that an absor

  • Q : What do you mean by the term alum What

    What do you mean by the term alum? Also illustrate its uses?

  • Q : Vant Hoff factor The Van't Hoff factor

    The Van't Hoff factor of the compound K3Fe(CN)6 is: (a) 1  (b) 2  (c) 3  (d) 4  Answer: (d) K3[Fe(CN)6] → 3K+

  • Q : Question related to colligative

    The colligative properties of a solution depend on: (a) Nature of solute particles present in it (b) Nature of solvent used (c) Number of solute particles present in it (d) Number of moles of solvent only

  • Q : Colligative effect Choose the right

    Choose the right answer from following. Which one of the statements written below concerning properties of solutions, explain a colligative effect: (a) Boiling point of pure water decreases by the addition of ethano (b) Vapour pressure of pure water d

  • Q : Problem based on mole concept Choose

    Choose the right answer from following. An aqueous solution of glucose is 10% in strength. The volume in which mole of it is dissolved will be : (a) 18 litre (b) 9 litre (c) 0.9 litre (d) 1.8 litre

  • Q : What are aliphatic amines and its

    In common system, the aliphatic amines are named by using prefix for alkyl group followed by the word amine.In case of mixed amines, the name of alkyl groups are arranged in alphabetical order. This is followed by the word amine. However, for simple secondary or tertiary amines anothe

  • Q : Mass percent Help me to go through this

    Help me to go through this problem. 10 grams of a solute is dissolved in 90 grams of a solvent. Its mass percent in solution is : (a) 0.01 (b) 11.1 (c)10 (d) 9

  • Q : Lowering of vapour pressure Help me to

    Help me to go through this problem. Lowering of vapour pressure is highest for: (a) urea (b) 0.1 M glucose (c) 0.1M MgSo4 (d) 0.1M BaCl2

  • Q : Units of Measurement Unit of

    Unit of measurement- These are also some systems for units:      (1) C.G.S.