Textbook Question
What stereoisomers do the following reactions form?
a.
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7. Substitution Reactions
Substitution Comparison
3:36 minutesProblem 6a
Textbook Question
What is the major product of each of the following reactions?
a. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The reaction involves an alcohol (OH group) reacting with HCl, which is a strong acid. This is a substitution reaction where the hydroxyl group (-OH) is replaced by a halide (Cl).
Step 2: Determine the mechanism. Since the alcohol is tertiary (the carbon attached to the -OH group is bonded to three other carbons), the reaction will proceed via an SN1 mechanism. This is because tertiary carbons stabilize the carbocation intermediate formed during the reaction.
Step 3: Protonation of the alcohol. The hydroxyl group (-OH) is protonated by HCl, forming water (H2O), which is a good leaving group. This step increases the likelihood of the leaving group departing.
Step 4: Formation of the carbocation. After the water molecule leaves, a tertiary carbocation is formed. This carbocation is highly stable due to hyperconjugation and inductive effects from the surrounding alkyl groups.
Step 5: Nucleophilic attack. The chloride ion (Cl⁻) from HCl acts as a nucleophile and attacks the carbocation, forming the final product, which is a tertiary alkyl chloride.
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Video duration:
3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, the hydroxyl group (OH) acts as a nucleophile, and when reacting with HCl, it can be substituted by a chloride ion (Cl-), leading to the formation of an alkyl chloride.
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Reactivity of Alcohols
Alcohols are organic compounds containing hydroxyl (-OH) groups, and their reactivity can vary based on the structure of the alcohol. In this reaction, the presence of HCl facilitates the conversion of the alcohol into a more reactive alkyl halide, which is often more favorable for further reactions, such as elimination or substitution.
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Mechanism of Reaction
Understanding the mechanism of the reaction is crucial for predicting the major product. The reaction typically proceeds via a two-step mechanism: protonation of the alcohol by HCl to form a better leaving group, followed by the nucleophilic attack by chloride ion, resulting in the formation of the alkyl chloride as the major product.
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