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Which of the following compounds exhibit...

Which of the following compounds exhibit chelation ?
(i) `o`-cresol
(ii) methyl salicylate(oil of wintergreen)
(iii) `o`-hydroxybenzonitrile
(iv) `o`-flurophenol
(v) `o`-iodophenol

A

`(ii),(iii),(iv)`

B

`(ii),(iii),(iv),(v)`

C

`(ii),(iv)`

D

`(i),(ii),(iv)`

Text Solution

Verified by Experts

The correct Answer is:
C
Chelation occurs only in `(ii)` where the `H` of the `OH` group forms hydrogen bonds with the `O of C = O` group , and `(iv)` , since `F` is highly electronegative and is approachable to the `H` of `OH` group :

In `(i)` the `H of OH` group can not form hydrogen bonds with the carbon of methyl group. In `(iii)` , although the `N of CN` is highly electronegative , the geometry is wrong for the nitrile : the `-C-=N` group, with diagonal `(sp)` carbon is linear. The linearity of `CN` places the `N` too far away from the `OH`. In `(v),I` is not sufficiently electronegative.
Other compounds exhibiting intramolecular hydrogen bonding are
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