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Paul Walden, the brilliant son of a farm...

Paul Walden, the brilliant son of a farmer succeeded in finding a concept that is now widely known as umbrella effect in `S_N2` reactions. In an `S_N2` reaction, the configuration at the reaction centre is inverted as a umbrella turns inside out in a strong wind. An ideal `S_N1` reaction, on the other hand, yield nearly racemised product as it proceeds through planar carbocation. `S_N2` reactions proceed smoothly on primary alkyl halide whereas tertiary halides are fit for `S_N1` mechanism. However, evidences indicate that all the molecules of particular substances do not necessarily react by a single mechanism.After all, the intention of the molecule is very clear, they want to follow the low energy path.If both paths have nearly the same energy barrier, then follow a mixed mechanism.For example, secondary alkyl halides follow a mixed mechanism, say 60% molecule react by `S_N2` and rest 40% by `S_N1` Stereochemical features, as mentioned above, are noticeable only when the reaction is carried out on a particular enantiomer.Even the reaction centres, which are paths of suitably substituted rings, also exemplify the said features.
A reaction gives the following results.

What should be the % age of back side attack assuming complete reactions ?

A

`65%`

B

`30%`

C

`35%`

D

`85%`

Text Solution

Verified by Experts

The correct Answer is:
A

Percentage of backside attack=Percentage of inversion + 1/2 (Percentage of racemisation) 70% racemisation and rest 30% inversion gives 65% backside attack.
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