Elimination question on alkyl halide

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    Elimination
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SUMMARY

The discussion centers on the elimination mechanism of alkyl halides, specifically involving the Finkelstein reaction and Newman projections. The user describes a process leading to the formation of trans-2-butene through anti elimination of erythro iodine from vicinal positions. The user contrasts their method with a solution manual that suggests a different mechanism, resulting in a cis alkene instead of the expected trans alkene. This discrepancy raises questions about the accuracy of the solution manual's approach versus the user's method.

PREREQUISITES
  • Understanding of Newman projections in organic chemistry
  • Familiarity with the Finkelstein reaction mechanism
  • Knowledge of anti elimination processes in alkyl halides
  • Concept of stereochemistry in alkene formation
NEXT STEPS
  • Research the detailed mechanism of the Finkelstein reaction
  • Study the implications of stereochemistry in elimination reactions
  • Learn about the differences between anti and syn elimination mechanisms
  • Examine case studies of alkyl halide reactions leading to different alkene isomers
USEFUL FOR

Chemistry students, organic chemists, and educators looking to deepen their understanding of elimination reactions and stereochemical outcomes in alkyl halide transformations.

Zayan
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Homework Statement
Find the major product
Relevant Equations
E1/E2/Sn1/Sn2
I firstly made the newman projection, aci/base on OH resulting in OH2+. Then NGP by neighbouring bromine and then the other bromine back attack. Then I simply did Finkelstein reaction and hence anti eliminating erythro iodine from vicinal positions making Trans 2 butene. The solution manual however has done something different. Normal external SN2 followed by Iodine removal(see the image). But the have done the anti elimination on threo iodine. It should give cis alkene, but they have given answer as trans alkene. So either I am somehow wrong, or the solution manual has done wrong mechanism. Please help.
Screenshot_2024-09-30-14-31-44-14_f9ee0578fe1cc94de7482bd41accb329.jpg
The above is the question.
Screenshot_2024-09-30-14-46-12-11_92460851df6f172a4592fca41cc2d2e6.jpg

This is the solution provided.
 

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