Textbook Question
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
b. HI
10. Addition Reactions
Hydrohalogenation
2:46 minutesProblem 12a(2)
Textbook Question
What is the major product of each of the following reactions?
2. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The given reaction involves an alkene (cyclohexene) reacting with HCl, which is an electrophilic addition reaction. This type of reaction typically follows Markovnikov's rule.
Step 2: Analyze the structure of the alkene. Cyclohexene has a double bond, which is the site of reactivity. The π electrons in the double bond will attack the proton (H⁺) from HCl, leading to the formation of a carbocation intermediate.
Step 3: Apply Markovnikov's rule. According to Markovnikov's rule, the hydrogen atom from HCl will add to the carbon of the double bond that already has more hydrogen atoms, while the chlorine atom will add to the carbon with fewer hydrogen atoms. This ensures the formation of the more stable carbocation intermediate.
Step 4: Consider carbocation stability. In this case, the carbocation formed is a secondary carbocation, which is relatively stable. No rearrangement is necessary as the secondary carbocation is already the most stable intermediate possible.
Step 5: Complete the reaction. The chloride ion (Cl⁻) will attack the carbocation, resulting in the formation of the major product, which is a chlorocyclohexane. The chlorine atom will be attached to the carbon that originally had fewer hydrogen atoms.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition Reactions
Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically seen in alkenes and alkynes. In this case, cyclohexene, an alkene, reacts with HCl, where the double bond acts as a nucleophile, attacking the electrophilic hydrogen in HCl. This reaction leads to the formation of a carbocation intermediate, which is crucial for determining the major product.
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Carbocation Stability
Carbocation stability is a key factor in determining the outcome of electrophilic addition reactions. More stable carbocations, such as tertiary carbocations, are favored over less stable ones. In the reaction of cyclohexene with HCl, the formation of a more stable secondary carbocation will influence the major product formed, as the reaction pathway will favor the route leading to the most stable intermediate.
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Markovnikov's Rule
Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of the reaction between cyclohexene and HCl, where the hydrogen from HCl will add to the less substituted carbon, leading to the formation of a more stable product through the carbocation mechanism.
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