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Published on: 18/09/2019
Aldehydes , Ketones and Carboxylic Acids
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Questions + Answers key
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1.
Write chemical reactions to effect the following transformations :
(i) Butan-1-ol to butanoic acid
(ii) Benzyl alcohol to phenylethanoic acid
(iii) 3-Nitrobromobenzene to 3-nitrobenzoic acid
(iv) 4-Methylacetophenone to benzene-1, 4-dicarboxylic acid
(v) Cyclohexene to hexane-1, 6-dioic acid
(vi) Butanal to butanoic acid
2.
Arrange the following in decreasing order of their acidic strength. Give explanation for the arrangement.
C6H5COOH, FCH2COOH, NO2CH2COOH.
3.
Compound 'A' was prepared by oxidation 'B' with alkaline KMnO4. Compound 'A' on reduction with lithium aluminium hydride gets converted back to compound 'B'. When compound 'A' is heated with compound B in the presence of H 2SO4 it produces fruitly smell of compound C to which family the compounds 'A', 'B' and 'C' belong to?
4.
What product will be formed on reaction of propanal with 2-methylpropanal in the presence of NaOH? What products will be formed? Write the name of the reaction also.
5.
A compound 'A' with molecular formula C5H10O gave positive 2, 4-DNP test but a negative Tollen's reagent test. It was oxdised to carboxylic acid 'B' with molecular formula C3H6O2 when treated with alkaline KMnO4 under vigorous condition. Sodium salt of 'B' gave a hydrocarbon 'C' on Kolbe's electrolytic reduction. Identify A, B and C and write the chemical equations for the reaction.
6.
Give chemical tests to distinguish between the following pairs of compounds:
(i) Propanoyl chloride and Propanoic acid
(ii) Benzaldehyde and Acetophenone
1.
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2.
O2NCH2COOH > FCH2COOH > C6H5COOH
-NO2 is more electron-withdrawing group than 'F' there, 2-nitroethanoic acid is most acidic and benzoic acid is least acidic due to greater hydrocarbon part and less solution solubility in water.
3.
'A' is carboxylic acid, 'B' is alcohol, 'C' is easter.
4.

5.
C5H10O gives positive 2, 4- DNP tesr but a negative Tollen's reagent test, therefore, it is a ketone since it gives carboxylic acid C3H6O2 on vigorous oxidiation, therefore it shold be 3-pentanone.
6.
(i) Add NaHO3 solution to each of them. Propanol chloride will not react whereas propanoic acid will give brisk effervescence due to CO2.
(ii) Add I2 and NaOH. Acetophenone will give yellow ppt. of iodoform whereas benzaldehyde will not react.
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