Physical Properties of Aldehydes, Ketones and Carboxylic Acids

Jasmine Grover logo

Jasmine Grover

Education Journalist | Study Abroad Lead

Aldehydes and ketones are the simple compounds that involve a carbonyl group (a carbon-oxygen double bond). They are simple in a way that they don not have other reactive groups such as -OH or -Cl attached directly to the carbon atom in the Carbonyl group. In this article, we will consider the simple physical properties of Aldehydes, Ketones and Carboxylic acids such as boiling points, solubility in water.

Key Terms: Organic chemistry, Alcohol, Ketones, aldehydes, carbon, compounds, water, atom, carbonyl group, carbon-oxygen double bond, carboxylic acids


Definition of Aldehydes and Ketones

[Click Here for Sample Questions]

Aldehydes and Ketones are part of the organic compound class. Organic compounds are characterised by the presence of a carbonyl group or carbon-oxygen double bond (-C=O). Since the electronegativity is different in carbon and oxygen, the bond in the carbonyl group is polar. They are particularly simple compounds because they do not have reactive groups like -OH or -Cl attached to the carbon atom in -C=O.

bond in the carbonyl group is polar

Bond in the carbonyl group 

In aldehydes, the carbonyl group is attached to carbon and hydrogen. As opposed to this, in ketones, the carbonyl atom is attached to two carbon atoms.

Also Read:


Physical Properties of Aldehydes and Ketones

[Click Here for Previous Year Questions]

The physical properties of aldehydes and ketones are as below.

Physical State

While Ethanal is a volatile liquid, Methanal is a gas at room temperature. Similarly, other aldehydes and ketones are either gas or liquid at room temperature.

Boiling Point

The boiling point of methanal is -19°C and for ethanol it is +21°C. For aldehydes and ketones, the boiling point increases with molecular weight and is also dependent on the strength of the intermolecular forces.
The compounds have higher boiling points than hydrocarbons and ethers of comparable molecular masses because of the weak molecular connection in aldehydes and ketones. But the boiling points are lower in comparison to that of alcohols with the same molecular masses because there is no intermolecular hydrogen bond.

Vander Waals Dispersion Force

Vander Waals Dispersion Force

Vander Waals Dispersion Force: The boiling point of aldehydes and ketones depend on the carbon atoms. When the molecules lengthen and the number of electrons increases, the bond increases and the boiling point increases.

Van Der Waals dipole-dipole attraction: Due to the presence of the double bond between carbon and oxygen, aldehydes and ketones are polar to each other. This leads to an attraction between the permanent dipoles and other molecules near it. This is what makes the boiling point of these compounds high.

This is also explained in the video below:

The table below lists the boiling points of compounds in increasing order of molecular mass.

Name of the compound Molecular mass Boiling point
n-Butane 58 273
Methoxymethane 60 281
Propoanal 58 322
Acetone 58 329
Propan-1-ol 60 370

Solubility

Aldehydes and ketones are soluble in water. The solubility decreases when the length of the alkyl chain increases. Aldehydes and ketones like methanol, ethanal and propanone are miscible in water of all quantities. These compounds cannot form hydrogen bonds on their own but are able to do so with water due to the dipole-dipole attraction.

Solubility

Solubility

Smell

All lower aldehydes have a strong and unpleasant smell. Other aldehydes and ketones have a pleasant smell. When the molecule size of the compounds increases, the smell becomes less pungent. Naturally occurring aldehydes and ketones are used regularly in flavouring agents and perfumes like vanilla flavouring.


Definition Carboxylic Acids

[Click Here for Sample Questions]

Carboxylic Acids are a part of the -COOH group or also called the carboxyl group. Carboxylic acids have a (C=O)OH group fixed to an R group. Here, R refers to the remaining part of the molecule. The carbonyl group attaches to a hydroxyl group thus making the name, carboxylic acids. These acids occur in nature but can also be manufactured in laboratories.

Carboxylic Acids

Carboxylic Acids​

Carboxylic acids are denoted by the formula R-COOH. The acids are polar in nature and also can be aliphatic (RCOOH) or fragrant (ArCOOH). Carboxylic acids are used in the manufacture of pharmaceuticals, food additives, polymers, solvents etc. Other examples of carboxylic acids include citric acids, acetic acids, adipic acids etc.


Physical Properties of Carboxylic Acids

[Click Here for Previous Year Questions]

Physical State

Carboxylic acids, at room temperature, are colourless liquids. These acids have nine carbon atoms or less. Higher acids are more waxy and are solid.

Boiling Point

Compared to aldehydes, ketones and other compounds of similar molecular masses, carboxylic acids have high boiling points. The reason behind such high boiling points is for the acid molecules ability to substantially associate with each other through intermolecular hydrogen bonding. The hydrogen bonds do not break up completely even in the vapour state as a result. Most carboxylic acids are present as dimers in the vapour state.

Acetic acid and dimer

Acetic acid and dimer​

Smell

At room temperature, carboxylic acids have shown to possess unpleasant odours.

Solubility

The more simple aliphatic components of carboxylic acids have four carbon atoms and are miscible or soluble in water. This is due to its ability to form hydrogen bonds with water. When the number of atoms in the carboxylic acids is increased, the solubility nature decreases. For higher members of the same group, the immiscibility nature can be attributed to its hydrophobic communication of the hydrocarbon part of the acid. However, they are able to become soluble in organic solvents that are less polar like alcohol, benzene, ether etc.

Read More:- 


Sample Questions

Ques. Organize the following compounds in increasing order of the boiling points: CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2 -O-C2H5, -O-C2H5.(1 mark)

Ans: The above stated compounds have molecular masses in the range of 72 to 74. Accordingly, in order of their molecular masses, the order of the boiling points are CH3CH2CH2CH3< H5C2 -O-C2H5 < CH3CH2CH2CHO < CH3CH2CH2CH2OH.

Ques. Aldehydes and Ketones have lower boiling points than corresponding alcohols. Why ? (Compartment All India 2012)(1 mark)

Ans: The boiling points of aldehydes and ketones are lower than that of corresponding alcohols because alcohols have strong hydrogen bonding in them which is absent in aldehydes and ketones.

Ques. Rearrange the following compounds in the increasing order of their boiling points: 
CH3 — CHO, CH3 — CH2 — OH, CH3 — CH2— CH3 (All India 2013)(1 mark)

Ans: The increasing order is as follows: CH3CH2CH3 < CH3CHO < CH3CH2OH

Ques. Give reason: The compound ethanal is soluble in water. (All India 2013)(1 mark)

Ans. Ethanal is soluble in water because of the hydrogen bonding it forms with water molecules once it is dissolved in water.

Ques.  Arrange the following in increasing order of their boiling points: Propanol, Propane, Propanal. (New Delhi 2017)(1 mark)

Ans: The order is as follows:

propane<propanal<propanol

Ques. Arrange the following in increasing order of their boiling points CH3CHO, CH3CH2OH, CH3OCH3, CH3COOH. (1 mark)(All India compartment 2017)

Ans: CH3OCH3<CH3CHO<CH3CH2OH<CH3COOH

Ques. What are carboxylic acids?(1 mark)

Ans: Carboxylic acids are organic compounds that have a carbon atom attached to an oxygen atom forming a double bond and to a hydroxyl group (-OH). The name carboxylic is derived from the carbonyl group (C=O) and the hydroxyl group.

Ques. What are some examples of carboxylic acids?(1 mark)

Ans: Some common examples of carboxylic acids are acetic acids, citric acids, butyric acids, formic acids, propionic acids etc.

Ques. What are aldehydes and ketones?(1 mark)

Ans: Aldehydes and Ketones are compounds that possess the carbonyl group. Aldehydes have the carbonyl group bonded to hydrogen atoms while ketones have it bonded to two carbon atoms.

Ques. Explain the effect of increasing the size of the carbon chain on boiling point of aldehydes and ketones.(1 mark)

Ans: The boiling point of aldehydes and ketones depend on the carbon atoms. When the molecules lengthen and the number of electrons increases, the van der Waals dispersion forces increase and the boiling point increases.


Previous Year Questions

Ques: Draw the structure of 4-chloropentan-2-one. (All India 2011) (1 mark)

Ans: 

Draw the structure of 4-chloropentan-2-one

Ques: Give a chemical test to differentiate between Benzoic acid and Phenol. (Comptt. Delhi 2012) (1 mark)

Ans: On a chemical test, Benzoic acid forms a brisk efferevescene with NaHCO3 solution but phenol does not respond to this test. 

Ques: Write the structure of the product that is formed in the following reaction. (Comptt. All India 2012) (1 mark)
Write the structure of the product that is formed in the following reaction

Ans: 

the structure of the product that is formed in the following reaction

Ques: Why is Ethanal soluble in water? (All India 2013) (1 mark)

Ans: Ethanal is soluble in water because of its H-bonding between the polar carbonyl group and water molecules.

Ques: Carboxylic acids do not give characteristic reactions of carbonyl group. Explain. (Comptt. Delhi 2013) (1 mark)

Ans: The carboxylic carbon is less electrophilic than the catbonyl carbon due to the possible resonance structure. 

The carboxylic carbon is less electrophilic than the catbonyl carbon due to the possible resonance structure. 

Ques: Arrange the following compound group in increasing order based on their property indicated: Propanol, Propane, Proanal (Boiling point). (Delhi 2017)

Ans: Propanol> Propanal> Propane (boiling point).

Ques: Write the reactions involved in the following: 
(i) Clemmensen reduction
(ii) Cannizzaro reaction (Delhi 2017) (2 marks)

Ans: (i) In Clemmensen reduction, the carbonyl group of aldehydes and ketones is reduced to CH2 group on the treatment with zinc amalgam and concentrated hydrochloric acid.

In Clemmensen reduction, the carbonyl group of aldehydes and ketones is reduced to CH2 group on the treatment with zinc amalgam and concentrated hydrochloric acid.

(ii) In Cannizzaro reaction, aldehydes which do not have an a-hydrogen atom undergo self oxidation and reduction with cone, alkali and produce alcohol and carboxylic acid salt. 

 In Cannizzaro reaction, aldehydes which do not have an a-hydrogen atom undergo self oxidation and reduction with cone, alkali and produce alcohol and carboxylic acid salt. 

Ques: Predict the products of the given reactions: (All India 2015) (3 marks)
Predict the products of the given reactions

Ans: 

Predict the products of the given reactions

Ques: (a) An organic compound A with molecular formula C8H8O forms an orange red precipitate with 2, 4-DNP reagent and gives yellow precipitate on on heating with I2 and NaOH. It does not reduce Tollen’s reagent nor Fehling’s reagent nor does it decolourize bromine water or Baeyer’s reagent. On drastic oxydation with chromic acid, it produces carboxylic acid W having molecular formula C7H6O2. Identify the compounds A and B and explain the reaction that is involved in it.
(b) Write the mechanism of esterification of carboxylic acids. (Comptt. Delhi 2012) (5 marks)

Ans: (a) (i) The molecular formula is C8H8O.

(ii) As it produces an orange red ppt with 2, 4-DNP reagent, therefore it must be either aldehyde or a ketone.

(iii) As it does not reduce Tollen’s reagent nor Fehling’s reagent, therefore solution A must be ketone.

(iv) A on treatment with I2 and NaOH gives yellow ppt,

A on treatment with I<sub>2</sub> and NaOH gives yellow ppt,

(v) It does not decolourize bromine water or Baeyer’s reagent, therefore the unsaturation of A is because of the benzene ring. 

It does not decolourize bromine water or Baeyer’s reagent, therefore the unsaturation of A is because of the benzene ring.

(b) The mechanism of Esterification of carboxylic acids,

(b) The mechanism of Esterification of carboxylic acids,

For Latest Updates on Upcoming Board Exams, Click Here: https://t.me/class_10_12_board_updates


Check-Out: 

CBSE CLASS XII Related Questions

  • 1.
    Which isomer of $C_4H_9Br$ is most reactive towards $S_N1$ reaction?


      • 2.
        Under what condition can a bimolecular reaction become kinetically first order?


          • 3.
            Give structures of A, B and C: Aniline $\xrightarrow{Br_2/H_2O}$ A $\xrightarrow{NaNO_2+HCl, 0-5^\circ C}$ B $\xrightarrow{H_3PO_2+H_2O}$ C


              • 4.
                What happens when acidic solution of potassium permanganate is allowed to stand for sometime ? Give the equation involved. What is this type of reaction called ?


                  • 5.
                    What are reducing sugars?


                      • 6.
                        Predict the alkene that would be formed by dehydrohalogenation of 1-Bromo-1-methylcyclohexane.

                          CBSE CLASS XII Previous Year Papers

                          Comments


                          No Comments To Show