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From each of the following pairs select ...

From each of the following pairs select the compound that will react faster with sodium iodide in acetone
(a) 2-Chloropropane or 2-bromopropane
(b) `underset(I)overset(I)("1-Bromobutane") or underset(II)overset(II)("2-bromobutane")`

A

(a)-I, (b)-I

B

(a)-I, (b)-II

C

(a)-II, (b)-I

D

(a)-II, (b)-II

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question, we need to determine which compound will react faster with sodium iodide (NaI) in acetone for each pair given. The reaction involves nucleophilic substitution (SN2 mechanism), and we will analyze the compounds based on steric hindrance and the nature of the leaving groups. ### Step-by-Step Solution: #### (a) Compare 2-Chloropropane and 2-Bromopropane: 1. **Identify the Compounds**: - 2-Chloropropane (C3H7Cl) - 2-Bromopropane (C3H7Br) 2. **Determine the Leaving Groups**: - Chlorine (Cl) is a poorer leaving group compared to Bromine (Br). - The bond strength of C-Cl is stronger than C-Br, making Br a better leaving group. 3. **Analyze Steric Hindrance**: - Both compounds have similar steric hindrance since they are both secondary alkyl halides. 4. **Conclusion**: - Since 2-Bromopropane has a better leaving group (Br), it will react faster than 2-Chloropropane with NaI in acetone. **Answer for (a)**: **2-Bromopropane** will react faster. #### (b) Compare 1-Bromobutane and 2-Bromobutane: 1. **Identify the Compounds**: - 1-Bromobutane (C4H9Br) - 2-Bromobutane (C4H9Br) 2. **Determine the Structure**: - 1-Bromobutane has a primary carbon attached to the bromine. - 2-Bromobutane has a secondary carbon attached to the bromine. 3. **Analyze Steric Hindrance**: - In SN2 reactions, primary alkyl halides (1-Bromobutane) have less steric hindrance compared to secondary alkyl halides (2-Bromobutane). - Less steric hindrance allows the nucleophile (I-) to approach the carbon more easily. 4. **Conclusion**: - 1-Bromobutane, being a primary alkyl halide, will react faster than 2-Bromobutane due to less steric hindrance. **Answer for (b)**: **1-Bromobutane** will react faster. ### Summary of Answers: - (a) **2-Bromopropane** reacts faster than 2-Chloropropane. - (b) **1-Bromobutane** reacts faster than 2-Bromobutane.
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Knowledge Check

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