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Which of the two stereoisomers of 4-t-bu...

Which of the two stereoisomers of 4-t-butylcyclohexyl iodide `(""^(127) I^(-))` will undergo `S_(N)^(2)` substitution with `""^(128)I^(-)` faster, and why?

A

A will react faster because it is the more stable of the two isomers

B

A will react faster because it will yield a more stable product, and the transition state for both reactions is of the same energy

C

A will react faster because the approach of `""^(128) I^(-)` can depart unhindered.

D

B will react faster because it is less stable than A, and the transition state for both reactions is of the same energy

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The correct Answer is:
D


- due to 1,3 repulsion I.G. tendeny increase so rate of reaction
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Comprehension The first demonstration of the stereochemistry of the S_(N^2) reaction was carried out in 1934 by Prof. E.D Hughes and his colleagues at the University of London. They allowed (R) -2- iodooctane to react with radioactive iodide ion (""^(**)I-) The rate of substitution (rate constant K_5 ) was determined by measuring the rate of incorporation of radioactivity into the alkyl halide. The rate of loss of optical acitivity from the alkyl halide (rate constant K_0 ) was also determined under the same conditions: What ratio K_0//K_s is predicted for each of the following stereochemical scenarios : For inversion reaction :

Comprehension The first demonstration of the stereochemistry of the S_(N^2) reaction was carried out in 1934 by Prof. E.D Hughes and his colleagues at the University of London. They allowed (R) -2- iodooctane to react with radioactive iodide ion (""^(**)I-) The rate of substitution (rate constant K_5 ) was determined by measuring the rate of incorporation of radioactivity into the alkyl halide. The rate of loss of optical acitivity from the alkyl halide (rate constant K_0 ) was also determined under the same conditions: What ratio K_0//K_s is predicted for each of the following stereochemical scenarios : For equal amounts of both retention and inversion ?

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MS CHOUHAN-ALKYL HALIDES (SUBSTITUTION REACTIONS)-LEVEL-2
  1. Which of the two stereoisomers of 4-t-butylcyclohexyl iodide (""^(127)...

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  2. Statement - 1 : Nucleophilicity order in polar-protic solvent is I^(-)...

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  3. Statement - 1 : CH(3) - CH(2) - Cl + Nal overset("Acetone") rarr CH(3)...

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  4. Encircle whichever of the following:

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  5. Encircle whichever of the following: undergoes S(N^2) reaction more...

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  6. Encircle whichever of the following: undergoes S(N^1) reaction more r...

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  7. Encircle whichever of the following: undergoes an E2 reaction to giv...

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  8. Encircle whichever of the following: reacts with Nal to give (Z) - 1...

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  9. Encircle whichever of the following: undergoes S(N^(1)) reaction mo...

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  10. Encircle whichever of the following : undergoes S(N^2) reaction mor...

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  11. Encircle whichever of the following : undergoes an E1 reaction more ...

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  12. Encircle whichever of the following : undergoes an S(N^1) reaction m...

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  13. Encircle whichever of the following : undergoes an S(N^2) reaction m...

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  14. Encircle whichever of the following : undergoes an E2 reaction more ...

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  15. Match the column :

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  16. Matrix :

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  17. Encircle whichever of the following : undergoes an S(N^2) reaction m...

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  18. Encircle whichever of the following : undergoes an S(N^1) reaction m...

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  19. Encircle whichever of the following : undergoes an S(N^1) reaction m...

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  20. Reativity : Circle the reaction that reacts FASTER by S(N^2) in each p...

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  21. Consider the potential energy diagram given below (X) Name the po...

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