
- A=
- B(+) -
- C(-) -
- D() -
View written solutionFree
Correct answer: A
-
Identify the substrate and reagent behavior
The reaction involves a benzylic halide of the type reacting with tert-butoxide .
Here, is:
- a strong base
- a bulky nucleophile/base
Therefore, it strongly favors elimination () over substitution.
-
Check possible pathways
Possible products shown are:
- Elimination product:
- Substitution products: with chiral possibilities:
-
Why elimination is favored
In benzylic halides, substitution can occur, but with the steric hindrance makes backside attack difficult.
The substrate has a suitable -hydrogen on the adjacent group, so an reaction can occur easily:
-
Stability of the alkene formed
The alkene obtained is which is stilbene, a highly stabilized alkene due to conjugation with two phenyl rings.
This makes elimination especially favorable.
-
Why substitution products are not major
If substitution occurred, it would give and depending on mechanism could give enantiomers.
However, because the reagent is bulky and strongly basic, substitution is minor compared with elimination.
-
Conclusion
Therefore, the major product is:
So the correct option is A.
Comparison with stored correct answer
Stored correct answer: A
My derived answer: A
They agree.
More from Haloalkanes and Haloarenes
- Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolorize the colour of bromine?2017 · MCQ
- 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition product. The number of possible stereoisomers for the product is :2017 · MCQ
- The increasing order of the reactivity of the following halides for the SN1 reaction is : Includes diagram2017 · MCQ
- Which one of the following reagents is not suitable for the elimination reaction ? Includes diagram2016 · MCQ
- Bromination of cyclohexene under conditions given below yields : Includes diagram2016 · MCQ
- The synthesis of alkyl fluorides is best accomplished by:2015 · MCQ
- In reactions, the correct order of reactivity for the following compounds: , , and is:2014 · MCQ
- The major organic compound formed by the reaction of 1, 1, 1– trichloroethane with silver powder is:2014 · MCQ