Place the following compounds in the order of their decreasing basicity: Guanidine, Urea, Amidine
A) Guanidine Amidine Urea
B) Guanidine Urea Amidine
C) Urea Guanidine Amidine
D) Amidine Guanidine Urea

Question

Place the following compounds in the order of their decreasing basicity: Guanidine, Urea, Amidine
A) Guanidine > Amidine > Urea
B) Guanidine > Urea > Amidine
C) Urea > Guanidine > Amidine
D) Amidine > Guanidine > Urea

Quizplus · Accepted Answer

Guanidine is the most basic due to its resonance stabilization that delocalizes the positive charge more effectively than in amidines or urea. Amidines are more basic than urea because they have a more accessible lone pair for protonation. Urea is the least basic because its lone pairs are involved in resonance with the carbonyl group, making them less available for protonation.

Place the Following Compounds in the Order of Their Decreasing