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PROBLEM 7.54

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Organic Chemistry
Found in: Page 291

Short Answer

Question: Pick the reactant or solvent in each part that gives the faster SN2 reaction.

  1. reaction of with OH- or CH3CH2Br
  2. reaction of CH3CH2CH2Cl NaOH or NaOCOCH3
  3. reaction of CH3CH2CH2I with -OCH3 in or DMSO

Answer

  1. The reaction of OH- with CH3CH2Br is faster as compared to the reaction between OH- and CH3CH2Cl .
  2. The reaction of CH3CH2CH2Cl with NaOH is faster.
  3. The reaction of CH3CH2CH2I with -OCH3 by using DMSO as a solvent will be faster.
See the step by step solution

Step by Step Solution

Factors affecting the SN2 reactions

The mechanism of the SN2 reactions depends upon the following factors:

  • The presence of strong nucleophiles favors the SN2 mechanism.
  • The use of a polar aprotic solvent also favors the SN2 reactions.
  • A better leaving group also increases the rate of a SN2 reaction.
  • The presence of a strong nucleophile also favors the SN2 reaction.

This is because the presence of a strong nucleophile will result in the formation of the transition state quickly. The rate of the reaction also depends upon the concentration of the nucleophile.

The faster SN2  reactions among the reactions are as follows:

a. The reaction of OH- with CH3CH2Br is faster as compared to the reaction between OH- and CH3CH2Cl .

This Br- is because the is a better leaving group as compared to the Cl- ion.

b. The reaction of CH3CH2CH2Cl with NaOH is faster. The NaOH will produce OH- which is a stronger nucleophile as compared to OCOCH3.

c.The reaction of CH3CH2CH2I with -OCH3by using DMSO as a solvent will be faster.

DMSO refers to dimethyl sulfoxide has a chemical formula of (CH3)2SO . It is a polar aprotic solvent. The rate of SN2 the reaction increases by using the aprotic solvent.

On the other hand, methanol (CH3OH) is a polar protic solvent and is unfavorable for the reactions.

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