OCHEM SN1 and SN2 Major Products

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In summary, the major product of 2,3-dichloro-3ethyhexane reacted with one equivalent of NaI in acetone would be 3-chloro-3-ethyl-2-iodohexane. However, with one equivalent of AgNO3 in methanol, the reaction would occur via SN1 mechanism with Ag+ removing a Cl- from the tertiary carbon, resulting in a different major product.
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cathy
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Homework Statement




Determination of Major Products in SN2 reactions?
What would be the major product of 2,3-dichloro-3ethyhexane reacted with:
1. one equvalent of NaI in acetone?
2. one equavelent of AgNO3 in methanol
and explain your reasoning.

Homework Equations



N/A

The Attempt at a Solution



I understand the first one. Iodide would be your nucleophile (Nu) here. The Cl on the C3 will not undergo Sn2 b/c the C3 is tertiary. But the Cl on C2 will in fact work for Sn2 b/c it is secondary. So the product would be 3-chloro-3-ethyl-2-iodohexane.
For the second once, with the AgNO3 in methanol, I am confused.
Would this reaction even occur? If so, could someone explain to me why?
 
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  • #2
cathy said:

Homework Statement




Determination of Major Products in SN2 reactions?
What would be the major product of 2,3-dichloro-3ethyhexane reacted with:
1. one equvalent of NaI in acetone?
2. one equavelent of AgNO3 in methanol
and explain your reasoning.

Homework Equations



N/A

The Attempt at a Solution



I understand the first one. Iodide would be your nucleophile (Nu) here. The Cl on the C3 will not undergo Sn2 b/c the C3 is tertiary. But the Cl on C2 will in fact work for Sn2 b/c it is secondary. So the product would be 3-chloro-3-ethyl-2-iodohexane.
For the second once, with the AgNO3 in methanol, I am confused.
Would this reaction even occur? If so, could someone explain to me why?

The second one proceeds by SN1 mechanism with Ag+ snatching out a Cl- from the tertiary carbon. Do you see why the Cl- from tertiary carbon is removed?
 

FAQ: OCHEM SN1 and SN2 Major Products

1. What is the difference between SN1 and SN2 reactions?

The main difference between SN1 and SN2 reactions is their reaction mechanism. SN1 reactions follow a two-step process, where the leaving group dissociates first and then the nucleophile attacks. On the other hand, SN2 reactions follow a one-step process, where the nucleophile attacks and displaces the leaving group simultaneously. SN1 reactions are also favored in polar protic solvents, while SN2 reactions are favored in polar aprotic solvents.

2. What factors influence the major product in SN1 and SN2 reactions?

The major product in SN1 and SN2 reactions is influenced by several factors, including the strength of the nucleophile and the leaving group, the steric hindrance around the reaction site, and the solvent used. Additionally, the stability of the carbocation intermediate in SN1 reactions and the stereochemistry of the reactants in SN2 reactions can also affect the major product.

3. How does the reaction rate differ between SN1 and SN2 reactions?

The rate of SN1 reactions is dependent on the concentration of the substrate, while the rate of SN2 reactions is dependent on the concentrations of both the substrate and the nucleophile. This means that SN1 reactions are first-order, while SN2 reactions are second-order. Additionally, SN1 reactions are typically slower than SN2 reactions due to the formation of a carbocation intermediate.

4. Can SN1 and SN2 reactions occur simultaneously?

Yes, SN1 and SN2 reactions can occur simultaneously if the reaction conditions allow for it. This may happen if the substrate has both a good leaving group and a good nucleophile attached to it, and the reaction takes place in a solvent that can support both SN1 and SN2 mechanisms. In this case, a mixture of products will be formed.

5. How can the major product in SN1 and SN2 reactions be predicted?

The major product in SN1 and SN2 reactions can be predicted by considering the reaction conditions and the characteristics of the reactants. For SN1 reactions, the major product will be the most stable carbocation intermediate, while for SN2 reactions, the major product will be the product with the least steric hindrance around the reaction site. Furthermore, knowledge of the reactivity of different nucleophiles and leaving groups can also aid in predicting the major product in these reactions.

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