Solution Found!
Which will occur at a larger wavenumber:a. the C-O stretch
Chapter 14, Problem 23P(choose chapter or problem)
Problem 23P
Which will occur at a larger wavenumber:
a. the C-O stretch of phenol or the C-O stretch of cyclohexanol?
b. the C=O stretch of a ketone or the C=O stretch of an amide?
c. the C-N stretch of cyclohexylamine or the C-N stretch of aniline?
Questions & Answers
QUESTION:
Problem 23P
Which will occur at a larger wavenumber:
a. the C-O stretch of phenol or the C-O stretch of cyclohexanol?
b. the C=O stretch of a ketone or the C=O stretch of an amide?
c. the C-N stretch of cyclohexylamine or the C-N stretch of aniline?
ANSWER:
Solution 23P
(a)
Electron delocalization causes the C - O bond of the phenol to have partial double bond character, whereas the C - O bond of the cyclohexanol is a pure single bond. Again we know as the bond order or bond strength increases the absorption occurs at larger wave number. So, the ’C - O’ stretch of the phenol occurs at larger wave number.