Why Is This Considered an SN2 Reaction?

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In summary, the given reaction between ethylbromide and potassium t-butoxide results in the formation of ethyl t-butyl ether through an SN2 mechanism due to the primary nature of the electrophile and lack of resonance stabilization of the carbocation intermediate.
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phEight
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Homework Statement



CH3CH2-Br + (CH3)3C-O¯+K ----> (CH3)3C-O-CH2CH3
ethylbromide + potassium t-butoxide ---> ethyl t-butyl either

can someone please tell me why this is a Sn2 reaction?


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The Attempt at a Solution


I figured it should be Sn1 because the nucleophile is tertiary, but that is not the case. Is it because O is primary? Even then the nucleophile seems very crowded for an Sn2 reaction. Thanks in advanced.
 
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  • #2
The whole reason why tertiary/secondary/primary substitution level matters is that it stabilizes the intermediate carbocation, i.e., substitution level matters on the electrophile, not the nucleophile. It doesn't matter whether the nucleophile is tertiary or primary.

CH3CH2-Br is synthetically equivalent to CH3CH2(+) - hence, it is the electrophile. Since the electrophile is primary, and there is no resonance stabilization of the carbocation, the reaction is likely to proceed by an SN2 mechanism.
 
  • #3



The reaction shown is indeed an Sn2 reaction. Sn2 reactions are characterized by a single step mechanism where the nucleophile attacks the substrate and simultaneously displaces the leaving group. This reaction mechanism is favored when the substrate is primary or secondary and the nucleophile is strong and unhindered. In this case, the substrate (ethylbromide) is primary and the nucleophile (t-butoxide) is strong and unhindered, making it a good candidate for an Sn2 reaction. The fact that the t-butoxide is tertiary does not hinder the reaction because it is not involved in the rate-determining step. The crowded nature of the t-butoxide does not affect the reaction because the bulky tert-butyl group is able to stabilize the intermediate carbocation, making it a favorable Sn2 reaction.
 

Related to Why Is This Considered an SN2 Reaction?

What is the difference between Sn1 and Sn2 reactions?

Sn1 (Substitution Nucleophilic Unimolecular) and Sn2 (Substitution Nucleophilic Bimolecular) reactions are two types of nucleophilic substitution reactions. The main difference between them is the rate-determining step. In Sn1 reactions, the rate of the reaction is determined by the formation of a carbocation intermediate, while in Sn2 reactions, the rate is determined by the attack of the nucleophile on the substrate.

What are the factors that influence the rate of Sn1 and Sn2 reactions?

The rate of Sn1 and Sn2 reactions can be influenced by several factors, including the strength of the nucleophile, the type of leaving group, the solvent polarity, and the steric hindrance of the substrate. In Sn1 reactions, the rate is also affected by the stability of the carbocation intermediate, while in Sn2 reactions, the rate is affected by the steric hindrance of the substrate and the leaving group.

Which type of reaction is favored by polar protic solvents?

Polar protic solvents, such as water and alcohols, favor Sn1 reactions. This is because these solvents stabilize the carbocation intermediate through hydrogen bonding, which increases the rate of the reaction. Additionally, polar protic solvents can also solvate the nucleophile and hinder its attack on the substrate, making Sn2 reactions less favorable.

Can a primary alkyl halide undergo an Sn1 reaction?

No, primary alkyl halides cannot undergo Sn1 reactions. This is because the formation of a primary carbocation is highly unfavorable due to the lack of neighboring alkyl groups to stabilize the positive charge. Therefore, primary alkyl halides mainly undergo Sn2 reactions.

What is the stereochemistry of Sn1 and Sn2 reactions?

Sn1 reactions typically result in a racemic mixture of products, meaning that both enantiomers are formed in equal amounts. This is because the carbocation intermediate can be attacked from either side. On the other hand, Sn2 reactions result in an inversion of stereochemistry, where the nucleophile attacks the substrate from the side opposite to the leaving group, resulting in the formation of the opposite enantiomer.

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