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Which of the following haloalkanes will undergo nucleophilic substitution most r

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Question: Which of the following haloalkanes will undergo nucleophilic substitution most readily? (2022)

Options:

  1. 1-chloropropane
  2. 2-chloropropane
  3. 3-chloropropane
  4. Bromobenzene

Correct Answer: 3-chloropropane

Exam Year: 2022

Solution: 

Tertiary haloalkanes like 3-chloropropane undergo nucleophilic substitution more readily due to steric hindrance and the stability of the carbocation formed during the reaction.

Which of the following haloalkanes will undergo nucleophilic substitution most r

Practice Questions

Q1
Which of the following haloalkanes will undergo nucleophilic substitution most readily? (2022)
  1. 1-chloropropane
  2. 2-chloropropane
  3. 3-chloropropane
  4. Bromobenzene

Questions & Step-by-Step Solutions

Which of the following haloalkanes will undergo nucleophilic substitution most readily? (2022)
  • Step 1: Understand what haloalkanes are. Haloalkanes are organic compounds that contain carbon, hydrogen, and halogen atoms (like chlorine, bromine, or iodine).
  • Step 2: Know what nucleophilic substitution means. This is a type of reaction where a nucleophile (a species that donates an electron pair) replaces a halogen atom in a haloalkane.
  • Step 3: Identify the types of haloalkanes. There are three main types: primary (1°), secondary (2°), and tertiary (3°) haloalkanes, based on the number of carbon atoms attached to the carbon with the halogen.
  • Step 4: Learn about steric hindrance. This refers to the crowding around the reactive site of a molecule. More crowding makes it harder for the nucleophile to attack.
  • Step 5: Understand carbocation stability. When a haloalkane undergoes nucleophilic substitution, it can form a carbocation (a positively charged carbon atom). Tertiary carbocations are more stable than primary or secondary ones.
  • Step 6: Conclude that tertiary haloalkanes, like 3-chloropropane, undergo nucleophilic substitution more readily because they form stable carbocations and have more steric hindrance, which favors the reaction.
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