Aldehydes, Ketones and Carboxylic Acids
Aldehydes, Ketones and Carboxylic Acids
Aldehydes, Ketones and Carboxylic Acids
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Assignment
Reasoning Questions
Class + 2
1. Arrange the following compounds in increasing order of their property as indicated:
(i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone
(reactivity towards HCN).
(ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH,CH3CH2CH2COOH
(acid strength).
(iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxy benzoic acid
(acid strength).
2. Which acid of each pair shown here would you expect to be stronger?
(i) CH3CO2H or CH2FCO2H
(ii) CH2FCO2H or CH2CICO2H
(iii) CH2FCH2CH2CO2 or CH3CHFCH2COOH
(iv)
3. Arrange the following compounds in increasing order of their boiling points:
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
4. Arrange the following compounds in increasing order of their reactivity in nucleophilic addition
reactions
(i) Ethanal, Propanal, Propanone, Butanone
(ii) Benzaldchyde, p-Tolualdehyde, p-Nitrobenzaidehyde, Acetophenone
5. Would you expect benzaldehyde to be more reactive or less reactive in nucleophilic addition reactions
than propanal? Explain your answer.
6. Arrange the following in order of increasing acidity:
(i) HCOOH, ClCH2COOH, CH3COOH
(ii) CH3COOH, (CH3)2CHCOOH, (CH3)3CCOOH
(iii) CICH2COOH, Cl2CHCOOH,Cl3CCOOH
(iv) ClCH2COOH, CH3CH2COOH, ClCH2CH2COOH, (CH3)2 CHCOOH, CH3COOH
(v) CH3COOH, Cl2CHCOOH, CH3CH2COOH, Cl3CCOOH, ClCH2COOH
(vi) HClO, HClO2, HClO3, HClO4
7. Accounts for the following:
(i) Carboxylic acids with five or fewer carbon atoms are water soluble butt, higher are insoluble.
(ii) Highly branched carboxylic acids are less acidic than unbranched acids.
(iii) Acetic acid can be halogenated in presence of phosphorus and chlorine but formic acid
cannot be halogenated in the same way.
(iv) mathCarbon-oxygen bond lengths in formic acid are 1.23 Å and 1.36 Å but in sodium
formate both carbon-oxygen bonds have same value i.e, 1.27 Å.
(v) Formic acid is stronger than acetic acid.
8. Account for the following:
(a) Roiling points of carboxylic acids are higher than those of corresponding aldehydes and ketones.
(b) The C - O bond in R - COOH is shorter than in R - OH.
(c) Acetic acid in the vapour state has a molecular mass of 120.
9. Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic
acid is a stronger acid than phenol. Why?
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Assignment
Chemical Reactions based questions
Class + 2
1. 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.
2. How will you bring about the following conversions in not more than two steps?
(i) Propanone to propene
(ii) Benzoic acid to benzaldehyde
(iii) Ethanol to 3-hydroxybutanal
(iv) Benzene to m-nitroacetophenone
(v) Benzaldehyde to benzophenone
(vi) Bromo benzene to l-phenylethanol
(vii) Benzaldehyde to 3-phenylpropan-l-ol
(viii) Benzaldehyde to -hydroxyphenylacetic acid
(ix) Benzoic acid to m-nitrobenzyl alcohol
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Assignment
Some special questions
Class + 2
1. An organic compound 'A' (M.F. C8H16O2) was hydrolysed with dilute H2SO4 to give a carboxylic acid
'B' and an alcohol 'C'. Oxidation of 'C' with chromic acid produced 'B'. 'C' on dehydration gives but-l-
ene. Write equations for the reactions involved.
2. An organic compound with the molecular formula, C 9H10O forms 2,4-DNP derivative, reduces
Tollens reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzene
dicarboxylic acid. Identify the compound.
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