Assignment

1. Check whether the following statements are true or false.

   1. Biomolecular nucleophilic substitution reaction (SN2) is stereospecific and proceeds with inversion of configuration. (True/False)
   2. SN2 reactions proceed more rapidly in solvents like water and alcohol than in aprotic solvents like DMF or DMSO. (True/False)
   3. Rates of SN1 reactions are affected by the concentration and nature of the nucleophile. (True/False)
   4. Rates of SN1 reactions decrease with a better leaving group. (True/False)
   5. The substitution of electron-donating groups to a nucleophile produces a better nucleophile. (True/False)
   6. The weaker the basicity of a group, the greater its leaving ability. (True/False)

2. Which of the following halides will react most rapidly in an SN2 reaction?

   1. CH₃F
   2. CH₃Cl
   3. CH₃Br
   4. CH₃I

3. Which of the following would not be a reasonable nucleophile in an SN2 reaction?

   1. NH₃
   2. NC⁻
   3. H₂O
   4. HO⁻

4. Consider the SN1 solvolysis of the following 1°-alkyl chlorides in aqueous ethanol: (a) CH₃CH₂CH₂Cl, (b) CH₂=CHCH₂Cl, (c) CH₃OCH₂Cl, (d) CF₃CF₂CH₂Cl. What is the order of decreasing reactivity?

   1. d > c > b > a
   2. c > b > a > d
   3. c > a > d > a
   4. a > d > b > c

5. Which of the following reagents would you expect to react with bromocyclopentane by an SN2 mechanism?

   1. C₂H₅OH
   2. C₂H₅O⁻ K⁺
   3. NaCN
   4. (CH₃)₃N