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 : Molarity 20mol of hcl solution requires

    20mol of hcl solution requires 19.85ml of 0.01 M NAOH solution for complete neutralisation. the molarity of hcl solution

  • 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 : What are heterogenous catalysis? Give

    When the catalyst exists in a different phase than that of reactants, it is said to be heterogeneous catalyst, and the catalysis is called heterogeneous catalysis. For example, SO2 can be oxidized to SO3

  • 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 : Solubility of a gas The solubility of a

    The solubility of a gas in water depends on: (a) Nature of the gas (b) Temperature (c) Pressure of the gas (d) All of the above. Can someone help me in finding out the right answer.

  • Q : Relative lowering in vapour pressure of

    Give me answer of this question. "Relative lowering in vapour pressure of solution containing non-volatile solute is directly proportional to mole fraction of solute". Above statement is: (a) Henry law (b) Dulong and Petit law (c) Raoult's law (d) Le-Chatelier's pri

  • Q : C-X bond length in halobenzene less

    C-X bond length in halobenzene less then C-X bond lengthin CH3-x

  • Q : Describe Point Groups. For any

    For any symmetric object there is a set of symmetry operations that, together, constitute a mathematical group, called a point group.It is clear from the examples that most molecules have several elements of symmetry. The H2O

  • Q : Decanormal and decinormal solution

    Provide solution of this question.10N/and 1/10N solution is called: (a) Decinormal and decanormal solution (b) Normal and decinormal solution (c) Normal and decanormal solution (d) Decanormal and decinormal solution

  • Q : Relative lowering of the vapour pressure

    Choose the right answer from following.The relative lowering of the vapour pressure is equal to the ratio between the number of: (a) Solute moleules and solvent molecules (b) Solute molecules and the total molecules in the solution (c) Solvent molecules and the tota

©TutorsGlobe All rights reserved 2022-2023.