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Aldehydes, Ketones and Carboxylic Acids

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

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-Methoxybenzoic acid (acid strength)

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alok kumar singh

Contributor-Level 10

1. Di-tertbutyl, ketone

2. +I effect donates e^- . Br group will show +I effect along the chain but as I effect is distance dependent effect it will die as the distance increase.+I effect of alkyl group will reduce the acidity of a compound whereas –I effect will increase the acidity, I effects are distance dependent, correct order will be (CH₃)₂CHCOOH< CH₃CH₂CH₂COOH< CH₃CH (Br)CH₂COOH < CH₃CH₂CH (Br)COOH.

3. As we know the electron releasing groups (ERG) reduces the acidic strength of the compound (via inductive effect) whereas the electron withdrawing group (EWG) will increase the acidic strength of compound, and methoxy group is

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

An organic compound (A) (Molecular 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). (C) On dehydration gives but-1-ene. Write equations for the reactions involved.(Intermediate)

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alok kumar singh

Contributor-Level 10

ANSWER: Given compound is having 8 carbons, and on reaction with chromic acid C is converted back into B, as chromic acid reaction couldn't add any carbon hence both alcohol and acid must contain 4 carbons and it is given in the question that on dehydration C will give but-1-ene so alcohol will be butan-1-ol (C) and acid will be butan-1-oic acid (B) and given reaction will be ester hydrolysis,

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

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

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alok kumar singh

Contributor-Level 10

Since the given compound with molecular formula C₉H₁₀O form a 2,4-DNP derivative and reduce Tollen's reagent, it must be an aldehyde. Since it undergoes cannizzaro reaction, therefore CHO group is directly attached to the benzene ring.

Since on vigorous oxidation, it gives 1,2-benzene dicarboxylic acid, therefore it must be ortho-substituted benzaldehyde. The only o-substituted aromatic aldehyde having molecular formula C₉H₁₀O is o—ethyl benzyldehyde all the reaction can show now be explained on the basis of this structure-

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

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

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alok kumar singh

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i) Taking two molecules of propanal, one which acts as a nucleophile and the other as an electrophile.

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

How will you convert ethanal into the following compounds?

(i) Butane-1,3-diol

(ii) But-2-enal

(iii) But-2-enoic acid

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alok kumar singh

Contributor-Level 10

1. Butane-1,3-diol -

Ethanol react dilute alkali produces 3-hydroxybutanal which on Reduction gives butane-1, 3-diol on reduction.

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Aldehydes, Ketones and Carboxylic Acids Aldehydes, Ketones and Carboxylic Acids

Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction.

(i) Methanal

(ii) 2-Methylpentanal

(iii) Benzaldehyde

(iv) Benzophenone

(v) Cyclohexanone

(vi) 1-Phenylpropanone

(vii) Phenylacetaldehyde

(viii) Butan-1-ol

(ix) 2,2-Dimethylbutanal

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alok kumar singh

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Ans

Aldehydes and ketones having at least one α-hydrogen undergo aldol The compounds

(ii) 2-methylpentanal

(v) cyclohexanone

(vi) 1-phenylpropanone

(vii) phenylacetaldehyde

contain one or more α-hydrogen atoms. Therefore, these undergo aldol condensation.

Aldehydes having no α-hydrogen atoms undergo Cannizzaro The compounds

(i) Methanal

(iii) Benzaldehyde

(ix) 2, 2-dimethylbutanal

do not have any α-hydrogen. Therefore, these undergo cannizzaro reactions.

Compound (iv) Benzophenone is a ketone having no α-hydrogen atom and compound (viii) Butan-1-ol is an alcohol. Hence, these compounds do not undergo either aldol condensation or canni

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