Q16 of 27 Page 1

Which one of the following compounds will undergo faster hydrolysis reaction by SN1 mechanism? Justify your answer.


OR


A compound is formed by the substitution of two chlorine atoms for two hydrogen atoms in propane. Write the structures of the isomers possible. Give the IUPAC name of the isomer which can exhibit enantiomerism.

C6H5CH2Cl will undergo faster hydrolysis reaction by SN1 mechanism.


Explanation:


C6H5CH2Cl will undergo faster hydrolysis reaction by SN1 mechanism. This is because the carbocation formed from C6H5CH2Cl is resonance stabilized. SN1 mechanism is favored by a stable carbocation. Therfore C6H5CH2Cl will undergo faster hydrolysis reaction by SN1 mechanism.


The resonance stabilization takes place in this fashion:



OR



or or or


The structures possible are given above:


1. Chlorine is on the second and third carbon atoms.


2. Chlorine is on the first and third carbon atoms.


3. Both the chlorine atoms are on the third carbon.


4. Both the chlorine atoms are on the Second carbon atom.


The structure which can show enantiomerism is- 1,2 dichloropropane


Enantiomers are non-super imposable mirror images of each other. This structure does not super impose with its mirror image, Therefore it can be expected to show enantiomerism.


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