Q1P 聽The聽聽C=O聽double bond has a ... [FREE SOLUTION]

Chapter 2: Q1P (page 93)

TheC=Odouble bond has a dipole moment of about 2.4Dand a bond length of about 1.23 鈩�.
Calculate the amount of charge separation in this bond.
Use this information to evaluate the relative importance of the following two resonance contributors:

(R is a general symbol for a carbon-containing group)

Short Answer

Expert verified

Amount of charge separation is 未 = 0.4065 e.
There is 40% of the second resonance structure and 60% of the first resonance structure in resonance equilibrium.

Step by step solution

Bond dipole moment

The polarity of an individual bond is measured as its dipole moment (渭) which can be defined as 渭 = 未脳 d , where the amount of charge at either end of the dipole is represented by 未 and the distance between the charges is represented by d . When common units are used, it can be written as:

渭 (in debyes) =4.8 脳未(electroncharge) 脳 d(in angstroms) .

Resonance structures

A single structural formula sometimes cannot explain all the properties of a compound that is given. In such cases, the compound may be represented by two or more structural formulae which differ from each other only in the arrangement of electrons. None of this structural formula alone can explain all the observed properties of the compound. The compound is then said to show resonance. The various structures are known as resonating structures.

Calculation of charge separation and relative importance of the resonating forms

(a) As per given data,

Dipole moment (渭) = 2.4D

Distance between the charges(d )= 1.23 鈩�

Now,

渭 (in debyes) =4.8 脳未(electroncharge) 脳 d(in angstroms)

鉄� 2.4D = 4.8 脳未脳 1.23 鈩�

鉄� 未 = 2.4 鈭� 4.8 脳 1.23

鉄� 未 = 2.4 鈭� 5.904

鉄� 未 = 0.4065 e

The amount 未 of charge separation is about 0.4065 e (electronic charge).

(b) The amount of charge separation is found to be 0.4065 which implies there is 40% of the second resonance structure and 60% of the first resonance structure in resonance equilibrium.