Question

15) Which SN2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A) $CH_3S^- + CH_3I \longrightarrow CH_3SCH_3 + I^-$ B) $CH_3SH + CH_3I \longrightarrow$ $H_3C \overset{+}{S}CH_3 + I^-$ C) $CH_3O^- + CH_3I \longrightarrow CH_3OCH_3 + I^-$ D) $CH_3OH + CH_3I \longrightarrow H_3C \overset{+}{O}CH_3 + I^-$ E) $CH_3S^- + CH_3Cl \longrightarrow CH_3SCH_3 + Cl^-$

          15) Which SN2 reaction would you expect to take place most rapidly? Assume that the
concentrations of the reactants and the temperature are the same in each instance.
A) $CH_3S^- + CH_3I \longrightarrow CH_3SCH_3 + I^-$ 
B) $CH_3SH + CH_3I \longrightarrow$ 
$H_3C \overset{+}{S}CH_3 + I^-$
C) $CH_3O^- + CH_3I \longrightarrow CH_3OCH_3 + I^-$
D) $CH_3OH + CH_3I \longrightarrow H_3C \overset{+}{O}CH_3 + I^-$
E) $CH_3S^- + CH_3Cl \longrightarrow CH_3SCH_3 + Cl^-$

15) Which SN2 reaction would you expect to take place most rapidly? Assume that the
concentrations of the reactants and the temperature are the same in each instance.
A) CH3S^- + CH3I ⟶ CH3SCH3 + I^-
B) CH3SH + CH3I ⟶
H3C +SCH3 + I^-
C) CH3O^- + CH3I ⟶ CH3OCH3 + I^-
D) CH3OH + CH3I ⟶ H3C +OCH3 + I^-
E) CH3S^- + CH3Cl ⟶ CH3SCH3 + Cl^-

Added by Joseph N.

Essential Organic Chemistry

Paula Yurkanis Bruice 3rd Edition

Chapter 8

Instant Answer

Solved by Expert Christopher Nilsen

Step 1

The rate of this step depends on the strength of the nucleophile and the steric hindrance around the carbon atom being attacked. A) CH3CHS + CHI: In this reaction, the nucleophile is CH3CHS, which is a weak nucleophile. Show more…

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Chapter 6 15) Which S2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A) CH3CHS + CHI B) CH3CHI + CHOCHI C) CH3CHOH + CHI D) CH3CHSCH3 + Cl E) CH3CHS + CHCl