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Q.

The mechanism of  reaction is given as :

Question Image

A student writes general characteristics based on the given mechanism as :

a) The reaction is favored by weak nucleophiles

b) R+ would be easily formed if the substituents are bulky

c) The reaction is accompanied by racemization.

d) The reaction is favored by non-polar solvents.

Which observations are correct?                   

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a

(a), (b) and (c)

b

(b) and (d)

c

(a) and (c)

d

(a) and (b)

answer is A.

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Detailed Solution

  • Given reaction is SN1 
  • SN1 reaction is independent of strength of nucleophiles. 
  • Generally, strong nucleophiles favor SN2, but in SN1, weak nucleophiles are favored. 
  • Order of stability of Alkyl carbocations  Ris 3º>2º>1º.  
  • Bulky carbocation (3º) is more stable and forms easily.
  • Increasing the bulkiness of carbocation increases the stability of carbocation.
  • In SN1, both inversion and retention can take place in equal ratio, giving a racemic mixture, if R-X is optically active.
  • SN1 is favorable in polar solvent due to the solvation of carbocation thus, increasing the stability of carbocation.
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