Multiple Choice
Choose the SN2 reaction that will occur the fastest.
7. Substitution Reactions
SN2 Reaction
3:43 minutesProblem 14e
Textbook Question
Predict the major products of the following substitutions.
e. 1-chloropentane + NaI →
Verified step by step guidance1
Step 1: Recognize the type of substitution reaction. This reaction involves 1-chloropentane (a primary alkyl halide) and sodium iodide (NaI). Sodium iodide is a good nucleophile, and the reaction is likely to proceed via an SN2 mechanism due to the primary nature of the alkyl halide.
Step 2: Understand the SN2 mechanism. In an SN2 reaction, the nucleophile (I⁻) attacks the carbon atom bonded to the leaving group (Cl) from the opposite side, leading to a single-step reaction where the leaving group is displaced.
Step 3: Identify the leaving group. In this case, the leaving group is chloride (Cl⁻), which is a relatively good leaving group. It will be replaced by the iodide ion (I⁻).
Step 4: Write the chemical equation for the substitution reaction. The reaction can be represented as:
Step 5: Predict the major product. The major product will be 1-iodopentane, as the iodide ion replaces the chloride ion in the SN2 reaction. The reaction proceeds with inversion of configuration at the carbon center, but since the carbon is not chiral, this detail does not affect the product's structure.
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Key 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, NaI provides iodide ions (I-) as the nucleophile, which can attack the carbon atom bonded to the chlorine in 1-chloropentane, leading to the formation of a new compound.
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SN2 Mechanism
The SN2 mechanism is a type of nucleophilic substitution characterized by a single concerted step where the nucleophile attacks the electrophile from the opposite side of the leaving group. This results in the inversion of configuration at the carbon center. In the reaction of 1-chloropentane with NaI, the SN2 pathway is favored due to the primary nature of the substrate.
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Leaving Group Ability
The ability of a leaving group to depart from a molecule is crucial in determining the outcome of substitution reactions. Chlorine, as a leaving group, is relatively good because it can stabilize the negative charge after leaving. The efficiency of the substitution reaction is influenced by the strength of the leaving group, with better leaving groups facilitating faster reactions.
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