- Atert-butyl ethyl ether; iso-butyl ethyl ether
- Btert-butyl ethyl ether; 2-butyl ethyl ether
- Ciso-butyl ethyl ether; tert-butyl ethyl ether
- D2-butyl ethyl ether; iso-butyl ethyl ether
View written solutionFree
Correct answer: C
-
Identify the substrate
2-Methyl propyl bromide means isobutyl bromide:
This is a primary alkyl bromide.
-
Reaction with
Ethoxide ion is a strong nucleophile. With a primary alkyl halide, the reaction proceeds mainly by mechanism.
So substitution occurs at the carbon bearing bromine:
The product is isobutyl ethyl ether.
Hence,
- Mechanism for formation of :
- iso-butyl ethyl ether
-
Reaction with
Ethanol is a weak nucleophile and a polar protic solvent. In such conditions, ionization is favored. The initially formed primary carbocation is unstable:
It undergoes 1,2-hydride shift to form the more stable tert-butyl carbocation:
Then ethanol attacks this carbocation:
So the reaction proceeds through with rearrangement, giving tert-butyl ethyl ether.
Hence,
- Mechanism for formation of :
- tert-butyl ethyl ether
-
Match with options
We found:
- : , iso-butyl ethyl ether
- : , tert-butyl ethyl ether
This matches Option C.
-
Comparison with stored answer
Stored correct answer = C
Our derived answer = C
Therefore, they agree.
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