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Aldehydes, Ketones and Carboxylic Acids

Short Answer Type

221. How will you convert ethanal into the following compounds?
But-2-enoic acid.

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Long Answer Type

222.

Write structural formulae and names of the four possible aldol condensation products from propanal and butanal. In each case, indicate which aldehyde served as nucleophile and which as electrophile.

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Short Answer Type

223. An organic compound with the molecular formula C₉H₁₀O forms 2, 4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.

The given molecular formula C₉H₁₀O forms 2,4 –DNP derivative and reduces tollen’s reagent. Therefore, the given compound must be an aldehyde. Again the compound undergoes cannizzaro reaction and on oxidation gives 1,2 –benzenedicarboxylic acid. Therefore, the –CHO group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted. Hence, the compound is 2-ethylbenzaldehyde.

The above mechanism is given as,

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224.

An organic compound (A) (Mol. formula C₈H₁₆O₂) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). Write equations for the reactions involved.

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225. Arrange the following compounds in increasing order of their property as indicated:

Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-hutyl ketone (reactivity towards HCN).

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226. Arrange the following compounds in increasing order of their property as indicated:

CH₃CH₂CH(Br)COOH, CH₃CH(Br)CH₂COOH, (CH₃)₂CHCOOH, CH₃CH₂CH₂COOH (acid strength).

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227. Arrange the following compounds in increasing order of their property as indicated:
Benzoic acid, 4-Nitrohenzoic acid, 3, 4-Dinitrobenzoic acid, 4-Methoxy benzoic acid (acidstrength).

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228. Give simple tests to distinguish between the following pairs of compounds:
Propanal and Propanone

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229. Give simple tests to distinguish between the following pairs of compounds:
Phenol and Benzoic acid

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230. Give simple tests to distinguish between the following pairs of compounds:
Pentan-2-one and Pentan-3-one

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Previous Year Papers

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Short Answer Type

Long Answer Type

Short Answer Type

223. An organic compound with the molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.

223. An organic compound with the molecular formula C₉H₁₀O forms 2, 4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.