Why Does C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl Undergo SN1 Reaction?

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In summary, the ascending order of reactivity for compounds undergoing SN1 reactions is C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl. This was determined in a past year question and is considered correct. This is because the compound (CH3)3 CCl has three electron-donating groups surrounding the (CH3)3 C+ ion, stabilizing the carbonium ion formed. Additionally, the phenyl group, which is an electron-withdrawing group, draws electrons away from the carbon atoms, resulting in a higher partial positive charge for the carbonium ion formed. This explains why the phenyl group does not exert a negative inductive effect.
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desmond iking
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i was told that the the ascending order of the compound undergo SN1 reaction is C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl... it's a past year question . I am sure tha ans is correct. Can someone explain why? Generally , the most reactive is the compound (CH3)3 CCl , Am i right? this is because the (CH3)3 C+ is surrounded by three electron donating group , so it stabilise the carbonium ion formed.btw , the phenyl is an electron withdawing group , it draw the elctrons away form the C atoms , making the partial positive charge of the carboium ion formed more higher...

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i was told that the phenyl exerts positive inductive effect? why the phenyl isn't exerts negative inductive effect?
 

1. Why does C6H5CH(Cl)CH3 undergo SN1 reaction?

C6H5CH(Cl)CH3 undergoes SN1 reaction because it contains a tertiary carbon atom which is highly susceptible to nucleophilic attack. The presence of the chlorine atom also helps to stabilize the carbocation intermediate, making it easier for the reaction to proceed.

2. Why does (CH3)3CCl undergo SN1 reaction?

(CH3)3CCl undergoes SN1 reaction because it also contains a tertiary carbon atom and a chlorine atom, which both contribute to the stability of the carbocation intermediate. Additionally, the bulky nature of the three methyl groups makes it easier for the leaving group (Cl) to dissociate, facilitating the reaction.

3. Why does C6H5C(CH3)2Cl undergo SN1 reaction?

C6H5C(CH3)2Cl undergoes SN1 reaction because it contains a secondary carbon atom, which is still susceptible to nucleophilic attack. The chlorine atom also helps to stabilize the carbocation intermediate, making the reaction favorable.

4. What is the order of reactivity in these molecules?

The order of reactivity in these molecules is C6H5CH(Cl)CH3 < (CH3)3CCl < C6H5C(CH3)2Cl. This is because the stability of the carbocation intermediate decreases as we move from tertiary to secondary to primary carbon atoms, making the reaction more difficult to proceed.

5. Can these molecules undergo SN2 reaction as well?

No, these molecules are not likely to undergo SN2 reaction because they all contain bulky substituents or groups that hinder the approach of the nucleophile. SN2 reactions require a backside attack, which is difficult to achieve in these molecules due to steric hindrance. Additionally, SN1 reactions are favored in polar protic solvents, while SN2 reactions are favored in polar aprotic solvents, and these molecules tend to undergo SN1 reactions in most cases.

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