Chapter 6: Problem 30
Treating 2-methylpropene with methanol in the presence of sulfuric acid gives tert-butyl methyl ether.
Short Answer
Expert verified
Answer: The reaction mechanism involves electrophilic addition, and specifically an acid-catalyzed nucleophilic substitution, in which the alkene is protonated by sulfuric acid, followed by a nucleophilic attack by methanol and the subsequent deprotonation to form the final product, tert-butyl methyl ether. The sulfuric acid catalyst is regenerated in the process.
Step by step solution
01
Identify the reactants and the catalyst in the reaction.
In this reaction, the reactants are 2-methylpropene (also known as isobutene) and methanol. The catalyst used is sulfuric acid.
2-methylpropene: CH2=C(CH3)2
Methanol: CH3OH
Catalyst: H2SO4 (sulfuric acid)
02
Identify the reaction type.
This reaction is an electrophilic addition reaction, specifically an acid-catalyzed nucleophilic substitution, since an electrophile (sulfuric acid) is added to the double bond of the alkene (2-methylpropene), and a nucleophile (methanol) replaces a proton.
03
Protonation of the alkene
In the presence of sulfuric acid, the alkene undergoes protonation. One of the double bonds of the alkene will accept a proton (H+) from the sulfuric acid, resulting in a carbocation intermediate.
CH2=C(CH3)2 + H2SO4 -> CH3-C+(CH3)2 + HSO4-
04
Nucleophilic attack of methanol
Next, the carbocation intermediate is attacked by methanol, a nucleophile. The oxygen atom in methanol will form a bond with the positively charged carbon atom in the carbocation intermediate, forming another intermediate with an -OH group.
CH3-C+(CH3)2 + CH3OH -> CH3-C(CH3)2-O-H + CH3
05
Deprotonation and the final product
In the last step, the intermediate with the -OH group loses a proton (H+), giving the final product and regenerating the sulfuric acid catalyst.
CH3-C(CH3)2-O-H + HSO4- -> CH3-C(CH3)2-O-CH3 + H2SO4
The final product is tert-butyl methyl ether (CH3-C(CH3)2-O-CH3).
Overall, the reaction mechanism involves the protonation of the alkene, nucleophilic attack by methanol, and deprotonation to give the final product, tert-butyl methyl ether, with the regeneration of the sulfuric acid catalyst.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Understanding 2-Methylpropene
2-Methylpropene, also known as isobutene, is a type of hydrocarbon that falls under the category of alkenes. Alkenes are characterized by having at least one double bond between carbon atoms. In the structure of 2-methylpropene, (CH2=C(CH3)2), the double bond exists between the first and second carbon atoms in the chain. This double bond is highly reactive, making 2-methylpropene a suitable reactant in many chemical reactions, such as electrophilic addition reactions.
2-Methylpropene's reactivity is attributed to the electrons in the double bond that can easily be targeted by electrophiles, which are species that are attracted to negative charge. In educational terms, imagine the double bond as a magnetic hotspot eagerly awaiting a match, which, in the context of our reaction, is provided by sulfuric acid. This inherent reactivity of 2-methylpropene is critical in synthesizing compounds like tert-butyl methyl ether.
2-Methylpropene's reactivity is attributed to the electrons in the double bond that can easily be targeted by electrophiles, which are species that are attracted to negative charge. In educational terms, imagine the double bond as a magnetic hotspot eagerly awaiting a match, which, in the context of our reaction, is provided by sulfuric acid. This inherent reactivity of 2-methylpropene is critical in synthesizing compounds like tert-butyl methyl ether.
Tert-Butyl Methyl Ether Synthesis
When discussing the synthesis of tert-butyl methyl ether, we're essentially looking at a process known as electrophilic addition, where a compound like isobutene reacts with a nucleophile, in this case, methanol. In simpler terms, synthesis here is about putting two molecules together with the help of a catalyst.
In the laboratory, the reaction is meticulously orchestrated by introducing the 2-methylpropene to methanol, with sulfuric acid serving as a catalyst. Through sequential steps—starting from the electrophilic attack on the double bond by an acid, followed by the binding of methanol to the reactive intermediary, and culminating in the release of the ether product—the synthesis is complete. Tert-butyl methyl ether is widely useful, serving as a solvent or as an additive that can help in fuel formulations. Its synthesis demonstrates a fundamental type of reaction mechanism students might encounter in organic chemistry.
In the laboratory, the reaction is meticulously orchestrated by introducing the 2-methylpropene to methanol, with sulfuric acid serving as a catalyst. Through sequential steps—starting from the electrophilic attack on the double bond by an acid, followed by the binding of methanol to the reactive intermediary, and culminating in the release of the ether product—the synthesis is complete. Tert-butyl methyl ether is widely useful, serving as a solvent or as an additive that can help in fuel formulations. Its synthesis demonstrates a fundamental type of reaction mechanism students might encounter in organic chemistry.
Role of Sulfuric Acid Catalysis
Sulfuric acid ((H2SO4)) plays a pivotal role in this type of chemical synthesis as a catalyst; it speeds up the reaction without being consumed in the process. How does it manage this? Simply put, sulfuric acid donates a proton ((H+)) to the 2-methylpropene, activating it towards the reaction.
Moreover, sulfuric acid's job doesn't end at the start. It sticks around to see the process through, regenerating itself at the end, ready to facilitate another molecular dance. This is a brilliant display of catalysis in action, a concept that finds parallels in numerous other reactions in organic chemistry. The acidic environment provided by sulfuric acid is essential for the reaction to proceed smoothly, ensuring that the reactants have the best possible chance of transforming into the desired tert-butyl methyl ether.
Moreover, sulfuric acid's job doesn't end at the start. It sticks around to see the process through, regenerating itself at the end, ready to facilitate another molecular dance. This is a brilliant display of catalysis in action, a concept that finds parallels in numerous other reactions in organic chemistry. The acidic environment provided by sulfuric acid is essential for the reaction to proceed smoothly, ensuring that the reactants have the best possible chance of transforming into the desired tert-butyl methyl ether.
Protonation and Nucleophilic Attack
These steps form the crux of the reaction mechanism. Protonation is akin to giving the 2-methylpropene a positive charge, making it an even more tempting target for nucleophiles—in this scenario, methanol. Think of a nucleophile as a chemical 'good samaritan' that donates an electron pair to a positively charged peer.
After the protonation, the methylpropene carbocation (a carbon atom with a positive charge) eagerly awaits a partner, and methanol steps in to form a bond, thereby completing the nucleophilic attack. This step-by-step sequence is essential in chemical synthesis and is reflected in many reactions across organic chemistry. Understanding protonation and nucleophilic attack is paramount for students, as it's not just about memorizing steps—it's about recognizing patterns of reactivity that govern the behavior of molecules.
After the protonation, the methylpropene carbocation (a carbon atom with a positive charge) eagerly awaits a partner, and methanol steps in to form a bond, thereby completing the nucleophilic attack. This step-by-step sequence is essential in chemical synthesis and is reflected in many reactions across organic chemistry. Understanding protonation and nucleophilic attack is paramount for students, as it's not just about memorizing steps—it's about recognizing patterns of reactivity that govern the behavior of molecules.