
- Aand follow mechanism
- Band follow mechanism
- CCompound undergoes inversion of configuration
- DThe order of reactivity for and is :
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Correct answer: B, C
This question asks to identify the correct statements regarding nucleophilic substitution reactions for four given compounds.
Let's first analyze the structure of each compound and its tendency to undergo or reactions.
Compound I: (Ethyl bromide)
- This is a primary () alkyl halide.
- It is sterically unhindered, favoring backside attack by a nucleophile.
- The primary carbocation () that would be formed in an reaction is highly unstable.
- Therefore, compound I strongly favors the mechanism.
Compound II: (Allyl bromide)
- This is a primary () allylic halide.
- Being a primary halide, it is unhindered and thus a good substrate for reactions. The rate is even enhanced due to the stabilization of the transition state by the adjacent -bond.
- The allyl carbocation () formed in an reaction is stabilized by resonance, so it can also undergo reactions under appropriate conditions (polar protic solvent, weak nucleophile).
Compound III: (tert-Butyl bromide)
- This is a tertiary () alkyl halide.
- It is sterically hindered, preventing backside attack required for the mechanism.
- The tertiary carbocation () formed upon departure of the bromide ion is very stable due to hyperconjugation and inductive effects.
- Therefore, compound III strongly favors the mechanism.
Compound IV: (1-Bromo-1-phenylethane)
- This is a secondary () benzylic halide.
- The carbocation formed in an reaction, , is a secondary benzylic carbocation. It is highly stabilized by resonance with the benzene ring.
- This high stability of the carbocation strongly favors the mechanism.
- However, being a secondary halide, it can also undergo reactions, especially with strong nucleophiles in polar aprotic solvents.
Now, let's evaluate each statement:
A: I and III follow mechanism
- Compound I () is a primary halide and undergoes reactions, not .
- Compound III () is a tertiary halide and undergoes reactions.
- Since the statement is not true for compound I, statement A is incorrect.
B: I and II follow mechanism
- Compound I () is a classic example of a substrate that undergoes reactions.
- Compound II () is a primary allylic halide, which is unhindered and readily undergoes reactions.
- Thus, statement B is correct.
C: Compound IV undergoes inversion of configuration
- Inversion of configuration is the stereochemical outcome of an reaction.
- Compound IV () is a chiral secondary benzylic halide. While it prefers the pathway in many conditions due to its stable carbocation, it can undergo an reaction under conditions that favor it (e.g., a strong, non-bulky nucleophile in a polar aprotic solvent).
- Since an pathway is possible for compound IV, it can undergo inversion of configuration.
- Therefore, statement C is correct.
D: The order of reactivity for I, III and IV is :
- The order of reactivity depends on the reaction mechanism.
- For reactions (favored by III and IV), reactivity depends on carbocation stability: .
- For reactions (favored by I), reactivity depends on steric hindrance: (III is essentially unreactive).
- The given order is inconsistent. The part suggests an trend, while suggests an trend. If we compare under conditions that allow both (like solvolysis), the order would be determined by carbocation stability, i.e., . The given order does not match any standard reactivity series.
- Therefore, statement D is incorrect.
Based on the analysis, the correct statements are B and C.
Comparison with Stored Answer: The stored answer is A, B, C. This is logically inconsistent. Statement A claims compound I follows the mechanism, while statement B claims it follows the mechanism. Both statements cannot be simultaneously correct. As established, compound I follows the mechanism, making statement A incorrect and statement B correct. Therefore, the stored answer key appears to be erroneous.
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