Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions

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Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions

By | November 2009
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Objective To compare the relative reactivities of different alkyl halides with two different reagents; sodium iodide in acetone and silver nitrate in ethanol. Below the reaction equations
1.RX+NAIRI+NAX (X=Cl or Br) in the presence of acetone
2.RX+AgNO3+EtOHROEt+AgX+HNO3
We used three substrates primary secondary and tertiary compounds are 1-bromobutane, 2-bromobutane and 2-bromo-2-methylpropane respectively to react with the two nucleophiles that are sodium iodide with acetone solvent and silver nitrate with ethanol solvent. Based on lab analysis and the reaction mechanism we can predict the reactivities of the substrates with the reagents and test the products STRUCTURES:

In the substitution mechanism there are two basic kinds of reaction SN1 and SN2 Both of them have similarities and differences.SN1 favors for tertiary carbon compounds and next secondary but unlikely for primary carbon compounds which is vice versa for SN2 mechanism. When compare both mechanisms instead of nucleophilic, SN1 the strength of nucleophilic is not important where as in SN2 needs strong nucleophilic; based on these behavior of reaction we can predict which reaction is SN1 and SN2. The nucleophilic characters are sodium iodide is strong and silver nitrate is weak.

no
substratesnucleophilic
Reaction(mechanism)
Sodium iodideSilver nitrate
11-bromobutanefastnoSN2
22-bromobutaneslowslowSN2 and SN1
32-bromo-2-methylpropanenofastSN1

Conclusion the nucleophilic of sodium iodide is strong and favors for primary carbon compound, the secondary carbon compound is slow reaction but we apply heat it react but no reaction at all in tertiary carbon compound, this is SN2. Silver nitrate is a weak nucleophile and a favor for tertiary carbon compound, the secondary carbon compound is slow reaction. Heat is needed for the secondary compound to react.
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