NCERT Solutions

Class 12 Chemistry

Aldehydes, Ketones and Carboxylic Acids

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Q.13

Give simple chemical tests to distinguish between the following pairs of compounds.

(i) Propanal and Propanone

(ii) Acetophenone and Benzophenone

(iii) Phenol and Benzoic acid

(iv) Benzoic acid and Ethyl benzoate

(v) Pentan-2-one and Pentan-3-one

(vi) Benzaldehyde and Acetophenone

(vii) Ethanal and Propanal

(i) Propanal and propanone can be distinguished by the following tests.

(a) Tollen’s test

Propanal is an aldehyde. Thus, it reduces Tollen’s reagent. But, propanone being a ketone does not reduce Tollen’s reagent.

 

(b) Fehling’s test

Aldehydes respond to Fehling’s test, but ketones do not.

Propanal being an aldehyde reduces Fehling’s solution to a red-brown precipitate of Cu2O, but propanone being a ketone does not. CH3CH2CHO + 2Cu+ + 5OH- CH3CH2COO-      + Cu2O       + 3H2O Propanal                                Propanoate ion  Red-Brown ppt.

 

(c) Iodoform test:

Aldehydes and ketones having at least one methyl group linked to the carbonyl carbon atom respond to iodoform test. They are oxidized by sodium hypoiodite (NaOI) to give iodoform. Propanone being a methyl ketone responds to this test, but propanal does not.

CH3COCH3 + 3NaOI CH3COONa     + CHI3      + 2NaOH

Propanone                 Sodium Acetate   Iodoform

                                                              (Yellow ppt)

(ii) Acetophenone and Benzophenone can be distinguished using the iodoform test.

Iodoform test:

Methyl ketones are oxidized by sodium hypoiodite to give yellow ppt. of iodoform.

Acetophenone being a methyl ketone responds to this test, but benzophenone does not.

C6H5COCH3 +           3NaOI                   C6H5COONa     +        CHI3      + 2NaOH

Acetophenone     Sodiumhypoiodite     Sodium Acetate    Iodoform

                                                                                          (Yellow ppt)

C6H5COCH3 + NaOI No yellow ppt. of CHI3

Benzophenone

(iii) Phenol and benzoic acid can be distinguished by ferric chloride test.

Ferric chloride test:

Phenol reacts with neutral FeCl 3 to form an iron-phenol complex giving violet colouration.

6C6H5OH + FeCl3 [Fe (OC6H5)6]3- + 3H+ + 3Cl-

Phenol                       Iron-phenol complex

                                (Violet colour)

But benzoic acid reacts with neutral FeCl 3 to give a buff coloured ppt. of ferric benzoate.

6C6H5OH       + FeCl3 (C6H5COO) 3Fe + 3HCl

Benzoic Acid                       Ferric benzoate 

                                          (Buff’s coloured ppt)

(iv) Benzoic acid and Ethyl benzoate can be distinguished by sodium bicarbonate test.

Sodium bicarbonate test:

Acids react with NaHCO3 to produce brisk effervescence due to the evolution of CO2 gas.

Benzoic acid being an acid responds to this test, but ethylbenzoate does not.

C6H5COOH + NaHCO3 C6H5COONa + CO2 (gas) + H2O

Benzoic Acid                 Sodium benzoate (Buff coloured ppt)

C6H5COOC2H5 +NaHCO3 No effervescence due to evolution of CO2 gas (v) Pentan-2-one and pentan-3-one can be distinguished by iodoform test.

Iodoform test:

Pentan-2-one is a methyl ketone. Thus, it responds to this test. But pentan-3one not being a methyl ketone does not respond to this test.

 

(vi) Benzaldehyde and acteophenone can be distinguished by the following tests.

  1. Tollen’s Test

Aldehydes respond to Tollen’s test. Benzaldehyde being an aldehyde reduces Tollen’s reagent to give a red-brown precipitate of Cu 2O, but acetophenone being a ketone does not.

C6H5CHO +      2[Ag (NH3)2] + + 3OH- C6H5COO-   +   2Ag +2H2O + 4NH3 Benzaldehyde   Tollen’s reagent          Benzoate ion Silver Mirror

 

  1. Iodoform test

Acetophenone being a methyl ketone undergoes oxidation by sodium hypoiodite (NaOI) to give a yellow ppt. of iodoform. But benzaldehyde does not respond to this test.

C6H5COCH3 +           3NaOI                   C6H5COONa     +        CHI3      + 2NaOH

Acetophenone     Sodiumhypoiodite     Sodium Benzoate    Iodoform

                                                                                          (Yellow ppt)

 

(vii) Ethanal and propanal can be distinguished by iodoform test.

Iodoform test

Aldehydes and ketones having at least one methyl group linked to the carbonyl carbon atom responds to the iodoform test. Ethanal having one methyl group linked to the carbonyl carbon atom responds to this test. But propanal does not have a methyl group linked to the carbonyl carbon atom and thus, it does not respond to this state.

CH3CHO + 3NaOI HCOONa + CHI3 + 2NaOH

Ethanal                   Sodium       Iodoform

                              Methanoate (yellow ppt)

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