Q25 of 30 Page 1

Answer the following questions :
(i) What is meant by chirality of a compound? Give an example.
(ii)Which one of the following compounds is more easily hydrolyzed by KOH and why?
CH3CHClCH2CH3 or CH3CH2CH2Cl

(iii) Which one undergoes SN2substitution reaction faster and why?




(i) Compounds which form mirror images and are non-superimposable to each other (existing as enantiomers) are known as chiral compounds. So, chirality is the property of a molecule to have non-superimposable mirror image. These molecules contain one asymmetric carbon atom. They do not have a plane of symmetry. Similarly, chiral carbon would mean that all the atoms bonded to that carbon atom are different.


Eg. Butan-2-ol



(ii) If the formation of a more stable intermediate is preferred, hydrolysis of that compound would be easier. So, hydrolysis of 2-chloro butane (CH3CHClCH2CH3) by KOH will result in the formation of secondary carbocation as an intermediate and hydrolysis of chloropropane (CH3CH2CH2Cl) will result in the formation of primary carbocation as an intermediate. We know, secondary carbocation is more stable than primary carbocation due to inductive effect hence hydrolysis of 2-chloro butane by KOH would be easier.


(iii) Iodine is a better leaving group as compared to chlorine because of its large size and less electronegativity, due to which it will be released at a faster rate during the nucleophilic reactions.


Also we know that, SN2 reactions prefer the formation of a better leaving group, so undergoes SN2 substitution reactions faster than .


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