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Which of the statements are WRONG about the nucleophilic addition reaction of alkenes and alkynes?

A

Addition of nucleophile `(Roverset(Ө)O)` to alkene gives an alkyl carbanion whose negative charge is on the `sp^3`-hydridised C atom.

B

Addition of nucleophile `(Roverset(Ө)O)` ot an alkyne gives a vinyl carbanion whose negative charge is on the `sp^2`-hybridised C atom. Due to more s character, it is readily formed and more stable than alkyl carbanion formed with alkenes. So alkynes are more reactive than alkenes towards NA reaction.

C

Strong electron-withdrawing inductive effect `(-I)` further stabilises both vinyl and alkyl carbanion.

D

Strong electron-donating inductive effect `(+I)` further stabilises both vinyl and alkyl carbanion.

Text Solution

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The correct Answer is:
To determine which statements are wrong about the nucleophilic addition reaction of alkenes and alkynes, we will analyze the properties and behavior of these compounds during the reaction. ### Step-by-Step Solution: 1. **Understanding Nucleophilic Addition:** - Nucleophilic addition involves the attack of a nucleophile (like RO⁻) on a carbon atom of a double or triple bond (alkene or alkyne). - The reaction leads to the formation of a carbon ion intermediate. **Hint:** Remember that nucleophiles are electron-rich species that seek positive centers. 2. **Formation of Carbon Ions:** - In the case of an **alkene**, the nucleophile attacks an sp³ hybridized carbon atom, resulting in a carbon ion with a negative charge on the sp³ carbon. - In the case of an **alkyne**, the nucleophile attacks an sp² hybridized carbon atom, leading to a carbon ion with a negative charge on the sp² carbon. **Hint:** Identify the hybridization of the carbon atom involved in the reaction to understand the stability of the resulting carbon ion. 3. **Stability of Carbon Ions:** - The carbon ion formed from an alkyne (vinyl carbon ion) is more stable than that formed from an alkene (alkyl carbon ion) because sp² hybridized carbons have more s-character, making them more electronegative and stabilizing the negative charge. **Hint:** Recall that the greater the s-character, the more stable the carbon ion due to increased electronegativity. 4. **Reactivity Comparison:** - Alkynes are more reactive than alkenes in nucleophilic addition reactions due to the stability of the carbon ion formed from alkynes. - Conversely, in electrophilic addition reactions, alkenes are more reactive than alkynes. **Hint:** Differentiate between nucleophilic and electrophilic addition reactions when considering reactivity. 5. **Effect of Inductive Effects:** - A strong electron-withdrawing group (−I effect) stabilizes the carbon ion by decreasing charge density, while a strong electron-donating group (+I effect) destabilizes it by increasing charge density. **Hint:** Remember that the nature of substituents on the carbon chain can significantly influence the stability of intermediates. 6. **Analyzing Statements:** - **Statement A:** "Addition of a nucleophile to an alkene gives an alkyl carbon ion whose negative charge is on the sp³ hybridized C atom." - This is correct. - **Statement B:** "Addition of a nucleophile on the alkyne gives the vinyl carbon ion whose negative charge is on the sp² hybridized carbon atom due to more s-character it is readily formed and hence is more stable than alkyl carbon ion formed with the alkenes." - This is correct. - **Statement C:** "Alkynes are more reactive than alkenes towards nucleophilic addition reactions." - This is correct. - **Statement D:** "Strong electron donating inductive effect further stabilizes both vinyl and alkyl carbon." - This is wrong; strong electron donating groups destabilize the carbon ions. ### Conclusion: The wrong statement about the nucleophilic addition reaction of alkenes and alkynes is **Statement D**.
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CENGAGE CHEMISTRY ENGLISH-ALKYNES-Exercises (Multiple Correct Answers Type)
  1. Which statement(s) is/are WRONG?

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  2. Which of the statements are correct about the reactivities of alkene, ...

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  3. Which of the statements are WRONG about the nucleophilic addition reac...

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  4. In the following sequence of reactions, Which of the statements a...

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  5. Acetylene is thermodynamically unstable and readily explodes, therefor...

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  6. Which of the statements are correct for alkyne with molecular formul...

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  7. For the conversion of alkyne to cis-alkene, H2+ Lindlar's catalyst is ...

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  8. i. Me--=-Hunderset((ii)H2O2//overset(Ө)OH)overset((i) Sia2BH)rarrA i...

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  9. Which of the following statements are correct?

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  10. Which of the following statement(s) is/are correct:

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  11. Compound (B) is same when (A) is:

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  12. Which of the statements are correct? R--=-R^'underset(+EtOH)overset(...

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  13. Which of the statements are correct? R--=-Runderset(Catalyst)overset...

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  14. Hydroboration oxidation and acid hydration will yield the same produ...

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  15. C4H6underset(1 mol)overset(H2+Pt)rarrC4H8overset(O3//H2O)rarr Acedic a...

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  16. All reagents, [Cu(NH3)2]^(o+), [Ag(NH3)2]^(o+), CH3MgBr, and NaNH2 r...

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  17. Compound (A) does not react with Tollens or Grignard reagent, but afte...

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  18. Compound (A) reacts with [Cu(NH3)2]^(+) and Tollens reagent, but after...

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  19. Which of the statements are correct?

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  20. Reagents used in conversion from (A) to (B) are:

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