Alcohols and Ethers - Result Question 28

####31. In the following reaction sequence, the correct structure (s) of X is (are)

(2018 Adv.)

(a)

(c) Me

(b)

(d) Me

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Answer:

Correct Answer: 31. (d)

Solution:

  1. Key idea All the reactions involved in the problem are Nucleophilic substitution of second order i.e., SN2 which have the speciality of inversion of configuration at the carbon atom involved.

Of the reactions given

Reaction 1 in its generalised format is seen as

ROH In diethyl ether (Et2O)PBr3RBr

Reaction 2 is simple halogen exchange reaction called Finkelstein reaction. Its generalised format is

RX+NaI In acetone (Me2CO)RI+NaX

where X=Cl or Br

Reaction 3 in its generalised format seen as

RI+NaN3HCONMe2RN3+NaI

Now if the given product is

and which is too enantiomerically pure i.e. 100 either dextrorotatory or leavorotatory form, then the ’ X ’ must be

Note The configuration at carbon * atom in ’ X ’ becomes inverted due to SN2 mechanism which is visible in the product as well.

Thus, the probable reactions will be



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