(a) Illustrate Sandmeyer's reaction with an equation.
(b) Explain why (CH₃)₂NH is more basic than (CH₃)₃N in aqueous solution.
(b) Explain why (CH₃)₂NH is more basic than (CH₃)₃N in aqueous solution.
Solution
(a)
(b) In water basicity = +I push \textit{plus} hydration of the cation. (CH)NH still has two N–H's for strong hydration; (CH)NH has one, and three methyls crowd the nitrogen — so the \textbf{secondary amine wins} despite the larger +I of the tertiary.
(b) In water basicity = +I push \textit{plus} hydration of the cation. (CH)NH still has two N–H's for strong hydration; (CH)NH has one, and three methyls crowd the nitrogen — so the \textbf{secondary amine wins} despite the larger +I of the tertiary.
CBSE Class 12 Board · Subjective