Questions: Which of the following two amides will react more readily with a nucleophile? Why?
Multiple Choice
1, because it is less hindered
II, because it is less hindered
1, because it is more strained
II, because it is more strained
Transcript text: Which of the following two amides will react more readily with a nucleophile? Why?
Multiple Choice
1, because it is less hindered
II, because it is less hindered
1, because it is more strained
II, because it is more strained
Solution
Solution Steps
Step 1: Identify the Amides
The two amides in question are:
Acyclic amide (left structure)
Cyclic amide (right structure)
Step 2: Analyze Steric Hindrance
Steric hindrance refers to the crowding around the reactive site of a molecule. The acyclic amide has less steric hindrance compared to the cyclic amide because the cyclic structure restricts the spatial arrangement of atoms, making it more crowded.
Step 3: Analyze Ring Strain
Ring strain occurs in cyclic compounds due to the angles between bonds being forced to deviate from their ideal values. The cyclic amide has more ring strain compared to the acyclic amide, making it more reactive as the molecule is under more stress and thus more likely to react to relieve this strain.