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5. A. Consider the following substitution reaction: Br CN NaCN DMSO + NaBr a) Determine whether the reaction proceeds via an SN1 or SN2 process? b) Draw the mechanism of this reaction c) What is the rate equation of this reaction?

5. A. Consider the following substitution reaction: Br CN NaCN DMSO + NaBr a) Determine whether the reaction proceeds via an SN1 or SN2 process? b) Draw the mechanism of this reaction c) What is the rate equation of this reaction?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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**5. A. Consider the following substitution reaction:** The reaction depicted involves the substitution of a bromide ion (Br) with a cyanide ion (CN) on a carbon chain. This is facilitated by sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO), producing a nitrile compound and sodium bromide (NaBr) as a byproduct. **Questions:** a) Determine whether the reaction proceeds via an SN1 or SN2 process. b) Draw the mechanism of this reaction. c) What is the rate equation of this reaction? **Explanation of the Reaction Process:** - **Reactants and Conditions:** The starting material is a carbon chain with a bromine atom attached. Sodium cyanide (NaCN) is used as the nucleophile, and the solvent is dimethyl sulfoxide (DMSO), which favors SN2 reactions due to its polar aprotic nature. - **Products:** The product is a carbon chain with a cyanide group attached (nitrile compound), and sodium bromide (NaBr) is produced as a byproduct. This setup suggests that the reaction likely goes through an SN2 mechanism, given the strong nucleophile (NaCN) and the solvent (DMSO). The reaction mechanism includes a backside attack by the cyanide ion, leading to inversion of configuration. **Graphical Element Description:** - The first carbon chain shows a bromine atom, which is replaced by a cyanide group in the product, indicated by the curved arrow from the reaction. - The "+" symbol separates the organic product from sodium bromide, indicating it is formed during the reaction.
Transcribed Image Text:**5. A. Consider the following substitution reaction:** The reaction depicted involves the substitution of a bromide ion (Br) with a cyanide ion (CN) on a carbon chain. This is facilitated by sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO), producing a nitrile compound and sodium bromide (NaBr) as a byproduct. **Questions:** a) Determine whether the reaction proceeds via an SN1 or SN2 process. b) Draw the mechanism of this reaction. c) What is the rate equation of this reaction? **Explanation of the Reaction Process:** - **Reactants and Conditions:** The starting material is a carbon chain with a bromine atom attached. Sodium cyanide (NaCN) is used as the nucleophile, and the solvent is dimethyl sulfoxide (DMSO), which favors SN2 reactions due to its polar aprotic nature. - **Products:** The product is a carbon chain with a cyanide group attached (nitrile compound), and sodium bromide (NaBr) is produced as a byproduct. This setup suggests that the reaction likely goes through an SN2 mechanism, given the strong nucleophile (NaCN) and the solvent (DMSO). The reaction mechanism includes a backside attack by the cyanide ion, leading to inversion of configuration. **Graphical Element Description:** - The first carbon chain shows a bromine atom, which is replaced by a cyanide group in the product, indicated by the curved arrow from the reaction. - The "+" symbol separates the organic product from sodium bromide, indicating it is formed during the reaction.
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