| Consider the reactions [AIPMT (M) 2011] |
| (i)\[{{(C{{H}_{3}})}_{2}}CH-C{{H}_{2}}Br\xrightarrow[{}]{{{C}_{2}}{{H}_{5}}OH}{{(C{{H}_{3}})}_{2}}CH\]\[-C{{H}_{2}}O{{C}_{2}}{{H}_{5}}+HBr\] |
| (ii)\[{{(C{{H}_{3}})}_{2}}CH-C{{H}_{2}}Br\xrightarrow[{}]{{{C}_{2}}{{H}_{5}}{{O}^{-}}}{{(C{{H}_{3}})}_{2}}CH\]\[-C{{H}_{2}}O{{C}_{2}}{{H}_{5}}+B{{r}^{-}}\] |
| The mechanisms of reactions CO and (ii) are respectively |
A) \[{{\text{S}}_{\text{N}}}\text{1}\,\text{and}\,{{\text{S}}_{\text{N}}}2\]
B) \[{{\text{S}}_{\text{N}}}\text{1}\,\text{and}\,{{\text{S}}_{\text{N}}}1\]
C) \[{{\text{S}}_{\text{N}}}2\,\text{and}\,{{\text{S}}_{\text{N}}}2\]
D) \[{{\text{S}}_{\text{N}}}2\,\text{and}\,{{\text{S}}_{\text{N}}}1\]
Correct Answer: A
Solution :
[a] \[{{C}_{2}}{{H}_{5}}OH\]being a weaker nucleophile, when used as a solvent in case of hindered 1° halide, favours \[{{S}_{N}}1\] mechanism while \[{{C}_{2}}{{H}_{5}}{{O}^{-}}\]being a strong nucleophile in this reaction favours \[{{S}_{N}}2\]mechanism.
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