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Haloalkanes react with potassium cyanide...

Haloalkanes react with potassium cyanide (KCN) to give alkyl cyanide, but gives alkyl isocyanide with silver cyanide (Ag CN).

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The cyanide ion is a resonance hybrid of the following structures:

CN-behaves as ambident nucleophile because it is capable of attacking through more than one site, i.e., Cand N. KCN is ionic in nature. Both C and N can donate electron pair. But C-N bond formed is weaker than C-C bond. So, attack occurs through C atom of cyanide group. As a result, alkyl cyanide is formed. AgCN is covalent in nature. Only N is free to donate electron pair. Alkyl isocyanide is formed as a main product,
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OMEGA PUBLICATION-HALOALKANES AND HALOARENES-MULTIPLE CHOICE QUESTIONS (MCQS)
  1. Haloalkanes react with potassium cyanide (KCN) to give alkyl cyanide, ...

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  2. Ethyl alcohol gives ethyl chloride with the help of

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  3. CH3 -CH =CH2 +HI to X where X is

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  4. The reaction CH3 -CH =CH2 +HBr to CH3 - underset(Br) underse...

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  5. SN^1 reaction of alkylhalides leads to

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  6. Most reactive metal is:

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  7. The reactivity order of halides for dehydrohalogenation is

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  8. Mg reacts with RBr best in

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  9. Both methane and ethane can be prepared in single step by the use of

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  10. Alkyl halides react with Mg in dry ether to form

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  11. Which of the following metal can be used for carrying out Wurtz-Fittig...

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  12. Ethyl alcohol gives ethyl chloride with the help of

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  13. CH3 -CH =CH2 +HI to X where X is

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  14. The reaction CH3 -CH =CH2 +HBr to CH3 - underset(Br) underse...

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  15. SN^1 reaction of alkylhalides leads to

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  16. Most reactive halide towards SNI reaction is

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  17. The reactivity order of halides for dehydrohalogenation is

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  18. Mg reacts with RBr best in

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  19. Both methane and ethane can be prepared in single step by the use of

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  20. Alkyl halides react with Mg in dry ether to form

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  21. Which of the following metal can be used for carrying out Wurtz-Fittig...

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