Question

Draw the products of each SN2 reaction and indicate the stereochemistry where appropriate.a. b. c.

Draw the products of each SN2 reaction and indicate the stereochemistry where appropriate.

a.


b.


c.

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Answer #1

Reaction takes place through the concerted mechanism (without formation of any intermediate). The nucleophile attacks on the carbon atom exactly opposite to the leaving group. So, the reaction product has inversion of the configuration.

(a)

(S)-1-chloro-1-duetiro ethane undergoes with methoxide ion to form (R)- 1-duetiro-1-methoxy ethane.

To get clear idea on stereo chemistry, rotate the molecule is shown below:

In this process, rotates the CH3, Cl and D parts anti-clock wise.

(b)

(S)-1-chloro-3-methylpentane undergoes with ethoxide ion to form a (S)-1-ethoxy-3-methylpentane. Here, the substitution reaction doesn’t takes place at chiral center. So, the reactant and product have same configuration.

(c)

(1R,3R)-1-bromo-3-methylcyclopentane undergoes with cyanide ion to form (1S,3R)-3-methylcyclopentanecarbonitrile.

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