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Example Questions
Example Question #51 :Organic Concepts
What is the product of the reaction shown?
This reaction is an example of a nucleophilic substitution on a secondary alkyl halide. The nucleophile in this case is cyanide (), and the atom that attacks in the cyanide ion is the carbon. Because cyanide is a good nucleophile, the reaction will occur viamechanism. The answer is thus the molecule where the bromide is replaced with cyanide.
Note: when nucleophilic substitution is performed using a nucleophile that contains carbon (Grignard reagents, acetylide reagents, cyanide, etc.) it is often easy to incorrectly count the number of carbons in the final product.
Example Question #52 :Organic Concepts
Which of these molecules would have a faster SN2 reaction?
Neither would react.
1-iodobutane
1-bromobutane
他们会the same rate.
1-iodobutane
is a better leaving group because it is a larger atom and thus has its negative charge spread more evenly. It is more stable and a weaker base than. The molecule with the leaving group that would be most stable, or the weakest base, is the molecule that would react fastest in an SN2 reaction.
Example Question #53 :Organic Concepts
Which of these would undergo a faster SN2 reaction?
2-bromobutane
They would react at the same rate.
1-bromopropane
Neither would undergo the reaction.
1-bromopropane
There would be more steric hindrance for a nucleophile in the 2-bromobutane because the leaving group, bromine, is located on a secondary carbon atom. A secondary carbon atom is attached to two other carbon atoms. The leaving group on the 1-propane is located on a primary carbon atom, which is attached to only one other carbon atom.
Example Question #54 :Organic Concepts
What is the rate law for this equation?
rate = k[R-Leaving Group]2
rate = k[R-Leaving Group]
rate = k[Nucleophile]2
rate = k[Nucleophile][R-Leaving Group]
rate = k[R-Leaving Group]
This reaction would occur using an SN1 mechanism because the leaving group is attached to a tertiary carbon, a carbon atom with three of the carbon atoms attached to it. The rate laws for SN1 mechanisms do not depend on the nucleophile concentration. The slow-step occurs unimolecularly within the molecule with the leaving group.