OCHEM SN1 and SN2 Major Products

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SUMMARY

The discussion focuses on determining the major products of SN2 and SN1 reactions involving 2,3-dichloro-3-ethylhexane. The major product for the reaction with one equivalent of NaI in acetone is identified as 3-chloro-3-ethyl-2-iodohexane, as the secondary chlorine at C2 undergoes SN2 substitution while the tertiary chlorine at C3 does not. In the reaction with one equivalent of AgNO3 in methanol, the mechanism is SN1, where Ag+ facilitates the removal of Cl- from the tertiary carbon, leading to the formation of a carbocation intermediate.

PREREQUISITES
  • Understanding of SN1 and SN2 reaction mechanisms
  • Familiarity with nucleophiles and electrophiles
  • Knowledge of carbocation stability and tertiary vs. secondary carbon reactivity
  • Basic principles of organic chemistry reactions
NEXT STEPS
  • Study the differences between SN1 and SN2 mechanisms in detail
  • Learn about nucleophilicity and its effect on reaction outcomes
  • Explore the role of solvents in influencing reaction mechanisms
  • Investigate the stability of carbocations and factors affecting their formation
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Organic chemistry students, educators, and anyone seeking to deepen their understanding of reaction mechanisms in organic synthesis.

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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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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?
 

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