- A

- B

- C

- D

View written solutionFree
Correct answer: C
- Write the substrate clearly
The compound is 3-bromo-2-fluoropentane:
In an E2 elimination, the leaving group is usually the better leaving group. Since
the elimination will occur mainly by removal of HBr, not HF.
So we consider elimination of a -hydrogen adjacent to the carbon bearing Br.
- Identify the -carbon and possible -carbons
The carbon bearing Br is carbon-3. Thus:
- -carbon =
- possible -carbons = adjacent carbons and
So two eliminations are possible:
(i) Elimination from
Remove H from and Br from :
This gives 2-fluoropent-2-ene.
(ii) Elimination from
Remove H from and Br from :
This gives 4-fluoropent-2-ene (or equivalently 2-fluoropent-3-ene depending on numbering convention).
- Decide the major product
Ordinarily, E2 reactions often give the more substituted alkene (Saytzeff product). However, here one of the possible alkenes has fluorine directly attached to a double-bond carbon (a vinylic fluoride):
Fluorine is strongly electron-withdrawing by the effect, which destabilizes this alkene relative to the alternative product. Therefore, the alkene with fluorine not directly on the double bond carbon in the same unfavorable way is preferred.
Hence the major product is:
- Conclusion
The major E2 elimination product of 3-bromo-2-fluoropentane is
This corresponds to option C.
- Comparison with stored answer
Stored correct answer: C
Our derived answer: C
So the derived answer agrees with the stored answer.
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