Question
Question: The most acidic hydrogen atoms are present in: A.ethane B. ethene C. ethyne D.benzene...
The most acidic hydrogen atoms are present in:
A.ethane
B. ethene
C. ethyne
D.benzene
Solution
The hybridisation of all the four compounds are needed to be taken out. After that, check for the s- character in each of them. Compound with the maximum percentage of s character will have most acidic hydrogen.
Complete answer:
In order to answer our question, we need to learn about the types of hybridisation:
i.sp-hybridisation: This is the simplest type of hybridisation involving s and p-orbitals. In this hybridisation one s and one p orbitals hybridise (or intermix) to produce two equivalent hybrid orbitals, known as sp hybrid orbitals. The orbitals that are suitable for sp hybridisation are s and pz, if z-axis is the axis that the hybrid orbitals are to lie along. The two sp-hybrid orbitals are arranged in a line fashion which makes an angle of 1800 and therefore the geometry of the molecule is linear. Each of the hybrid orbitals has 50% s-character and 50% p-character. This type of hybridisation is referred to as diagonal hybridisation.
ii. sp2hybridisation: In sp2 hybridisation one s and two p (px and py) orbitals of one atom hybridize to give three equivalent sp2 hybrid orbitals. These three sp2 hybrid orbitals are directed towards the three corners of an equilateral triangle with an angle of 1200 and give a triangular geometry to the molecule. sp2 hybrid orbitals are larger in size than sp-hybrid orbitals but slightly smaller than that of sp3 hybrid orbitals. Each sp2 hybrid orbitals has 1/3 (or 33.33%) s-character and 2/3 (or 66.7%) p-character.
iii.sp3 hybridisation: In this hybridisation one s and three p-orbitals intermix to form sp3 hybrid orbitals of equivalent energy and identical shape. These four sp3 hybrid orbitals are directed towards the four corners of a tetrahedron separated by an angle of 109028′. sp3 hybrid orbitals have 25% s-character and 75% p-character.
Now, more the s character, more the acidic character of hydrogen. Following table shows the data:
Compound | Formula | Hybridisation | % s character |
---|---|---|---|
Ethane | CH3−CH3 | sp3 | 25% |
Ethene | CH2=CH2 | sp2 | 33.33% |
Ethyne | CH≡CH | sp | 50% |
Benzene | C6H6 | sp2 | 33.33% |
As ethyne has the maximum s character, so it should have the most acidic hydrogen too. So,we obtain option C as the correct answer for this question.
Note:
In ethyne molecules, C≡C bond consists of one sp−sp σ-bond along with two π-bonds. The C≡Cbond length is 120 pm. C-H bond is sp-s sigma bond. The H-C-C angle is 1800, i.e., the molecule is linear.