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)

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 ERG, and nitro group is EWG, Increasing number of EWG will increase the effect and acidity too. Hence final order will be Methoxy benzoic acid< Benzoic acid<4-Nitrobenzoic acid<3,4-Dinitrobenzoic acid.

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

9 months ago

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 d