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As SN2 reaction at an asymmetric carbon ...

As `S_N2` reaction at an asymmetric carbon of a compound always gives:

A

an enantiomer of the substrate

B

a product with opposite optical rotation

C

a mixture of diastereomers

D

a single stereoisomer

Text Solution

Verified by Experts

The correct Answer is:
D

In `S_(N^(2))` reaction, an optically active alkyl halide gives an optically active product. The product may not have opposite optical rotation to that of the alkyl halide as the two are not enantiomers. Therefore, a single stereoisomer is the product.
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As S_(N^(2)) reaction at an asymmetric carbon of a compound always gives:

The high reactivity of alkyl halides can be explained in tems of nature of C-X bond which is highly polarised covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reaction of alkyl halides which mostly occur by S_(N^(1)) and S_(N^(2)) mechanisms. S_(N^(1)) reaction is a two step process and in the first step R-X ionises to give carbocation (slow process). In the second step the nucleophilic attacks the carbocation from either side to form the prodcut (fast process) . In S_(N^(1)) reaction there can be reacemization and inversion . S_(N^(1)) reaction is favoured by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R_(3)C-Xgt R_(2)CH-Xgt R_CH_(2)X gt CH_(3)X. " In " S_(N^(2)) reaction the strong nucleophilie OH^(-) attacks from the opposite side of the chlorine atom to give an inyermediate (transition state). which breaks to yield the product (alcohol) and leaving (X^(-)) group. The alcohol has a configuration opposite to that of the bromide and is said to proceed with inversion of configuration. S_(N^(2)) reaction is favoured by small groups on the carbon atom attached to halogen i.e., CH_(3)-X gt R-CH_(2)X gt R_(2) CHX gt R_(3) C-X An S_(N^(2)) reaction at an asymmetric carbon of a compound always gives:

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An SN^(2) reaction at an asymmetric C of a compound always gives:

An S_(N^(2)) reaction at an asymmetric carbon of a dextro-alkyl halide always gives

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DINESH PUBLICATION-ORGANIC COMPOUNDS WITH FUNCTIONAL GROUP CONTAINING HALOGENS -Selected Straight Objective Type MCQs
  1. Which of the following has the highest nucleophilicity ?

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  2. The reaction of propene with HOCl proceeds via the addition of :

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  3. As SN2 reaction at an asymmetric carbon of a compound always gives:

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  4. The number of isomers for the compound with molecular formula C(2)BrCl...

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  11. The major product obtained when Br2"/"Fe is treated with

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  12. How will you convert butan -2-one to propanoic acid?

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  13. The correct order of nucleophilicity among the following is: (I) CH(...

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  14. Among the following, the strongest nucleophile is:

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  15. The major product formed in the following reation is CH(3)-underset(...

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  16. The major product obtained on treatment of CH(3)CH(2)CH(F) CH(3) " wit...

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  17. Given the number of N and M

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  18. Which of the following sequence of reaction (reagents) can be used for...

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  19. The major product obtained on monobromination (with Br(2)//FeBr(3)) of...

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  20. Which of the following compounds has the highest boiling point ?

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