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The increasing order of the rate of HCN ...

The increasing order of the rate of HCN addition to compound A-D is
(A) HCHO
(B) `CH_(3)COOH_(3)`
( C) `PhCOCH_(3)`
(D) `PhCOPh`

A

`A lt B lt C lt D`

B

`D lt B lt C lt A`

C

`D lt C lt B lt A`

D

`C lt D lt B lt A`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the increasing order of the rate of HCN addition to the given compounds (A-D), we need to analyze the structure of each compound and the effect of substituents on the carbonyl carbon's electrophilicity. ### Step-by-Step Solution: 1. **Identify the Compounds**: - (A) HCHO (formaldehyde) - (B) CH₃COOH (acetic acid) - (C) PhCOCH₃ (acetophenone) - (D) PhCOPh (benzophenone) 2. **Understand the Mechanism**: - The reaction involves HCN acting as a nucleophile that attacks the electrophilic carbon of the carbonyl group (C=O). - The rate of this nucleophilic addition reaction depends on the electrophilicity of the carbonyl carbon, which is influenced by the substituents attached to it. 3. **Analyze the Electrophilicity**: - **Formaldehyde (A)**: Has no electron-donating groups, making the carbonyl carbon highly electrophilic. Thus, it reacts quickly with HCN. - **Acetic Acid (B)**: The -COOH group is an electron-withdrawing group, but the -CH₃ group is weakly electron-donating. The overall effect is that the carbonyl carbon is less electrophilic than in formaldehyde but more than in ketones. - **Acetophenone (C)**: The phenyl group (Ph) is a weak electron-donating group, which decreases the electrophilicity of the carbonyl carbon compared to acetic acid. - **Benzophenone (D)**: Both phenyl groups are electron-donating, making the carbonyl carbon the least electrophilic among the four compounds. Therefore, it reacts the slowest with HCN. 4. **Order of Reactivity**: - Based on the analysis, the increasing order of the rate of HCN addition is: - (D) PhCOPh < (C) PhCOCH₃ < (B) CH₃COOH < (A) HCHO 5. **Final Answer**: - The increasing order of the rate of HCN addition to compounds A-D is: - (D) < (C) < (B) < (A)
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AAKASH INSTITUTE ENGLISH-ALDEHYDES, KETONES AND CARBOXYLIC ACIDS -Assignment (Section A Competition Level Questions)
  1. Select the reagent for the following reaction:

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  2. An organic compound (X) with molecular formula C(9)H(10)O gives positi...

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  3. The increasing order of the rate of HCN addition to compound A-D is ...

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  4. The correct order of reactivity of PhMgBr with underset((I))(Ph-unde...

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  5. Identify 'X'

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  6. The diketone CH(3)-overset(overset(O)(||))(C)-(CH(2))(2)-overset(over...

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  7. What will be the product , when carboxy phenol, obtained by Reimer Tie...

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  8. Which of the following aromatic acids is most acidic?

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  9. CH(3)COOH overset (Delta) underset (P(2)O(5)) to X. Identify X

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  10. Which one of the following orders of acidic strength is correct?

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  11. Which of the following represents the correct order of acidity in the ...

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  12. The correct order of acidic strength is

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  13. Treatment of benzoic acid with Cl(2)//FeCl(3) will give

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  14. In esterfication

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  15. Acetyl chloride is reduced with LiAlH(4) , the product formed is

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  16. The reaction CH(3) COOH + Cl(2) overset (red P) to CICH(2) COOH + HC...

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  17. Saponification of ethyl benzoate with caustic soda as alkali gives

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  18. Which of the following acids has the smallest dissociation constant?

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  19. Which of the following compounds will show the maximum ‘enol’ content?

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  20. Aliphatic aldehyde can be oxidised by

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