Question

Rank the following compounds in order of their expected reactivity toward $\mathrm{S}_{\mathrm{N}} 2$ reaction: $$ \mathrm{CH}_{3} \mathrm{Cl}, \mathrm{CH}_{3} \mathrm{OTos}, \mathrm{CH}_{3} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl} $$

          Rank the following compounds in order of their expected reactivity toward $\mathrm{S}_{\mathrm{N}} 2$ reaction: 
$$
\mathrm{CH}_{3} \mathrm{Cl}, \mathrm{CH}_{3} \mathrm{OTos}, \mathrm{CH}_{3} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}
$$

Added by Anne E.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

04/04/2022

Step 1

Step 1: Determine the nature of the compounds - CH3Cl is a primary alkyl halide, CH3OTos is a primary alkyl tosylate, CH3NH2 is a primary amine, and (CH3)2CHCl is a secondary alkyl halide. Show more…

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Rank the following compounds in order of their expected reactivity toward $\mathrm{S}_{\mathrm{N}} 2$ reaction: $$ \mathrm{CH}_{3} \mathrm{Cl}, \mathrm{CH}_{3} \mathrm{OTos}, \mathrm{CH}_{3} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl} $$