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Applications of hybridisation

         (i) Size of the hybrid orbitals : Since s- orbitals are closer to the nucleus than p- orbitals, it is reasonable to expect that greater the s character of an orbital the smaller it is. Thus the descending order of the length of the three hybrid orbitals is opposite to that of the decreasing order of s orbital character in the three hybrid orbitals.

         sp3 > sp2>sp

         (ii) Electronegativity of different orbitals

         (a) Electronegativity of s-orbital is highest.

         (b) Electronegativity of hybrid orbital    % s-character in hybrid orbitals

738_applications of hybridisation.png

         Thus sp-hybrid carbon is always electronegative in character and sp3- hybrid carbon is electropositive in character. Sp2-hybrid carbon can behave as electropositive (in carbocation) as well as electronegative (in carbanion) in character.

484_applications of hybridisation1.png

         (c) Electronegativities of distinct hybrid and unhybrid orbitals in decreasing order is as follows

2184_applications of hybridisation2.png

         (iii) Bond length variation in hydrocarbons

         % of s orbital character

2060_applications of hybridisation3.png

Table : 

Bond type (C - H)

Bond length

Bond type (C - C)

Bond length

sp3 - s (alkanes)

1.112Å

sp3 - sp3 (alkanes)

1.54 Å

sp2 - s (alkenes)

1.103Å

sp2 - sp2 (alkenes)

1.34Å

sp - s (alkynes)

1.08Å

sp - sp (alkynes)

1.20Å

       (iv) Bond strength in hydrocarbons : The shorter is the bond size, the greater is the compression between molecules atomic nuclei and hence greater is the strength of that bond.

Table : 

Bond type (C - H)

Bond energy

(kcal/mole)

Bond type (C - C)

Bond energy

(kcal/mole)

sp3 - s

 (in alkanes)

104

sp3 - sp3

(in alkanes)

80 - 90

sp2 - s

 (in alkenes)

106

sp2 - sp2

(in alkenes)

122 - 164

sp - s 

(in alkynes)

121

sp - sp

(in alkynes)

123 - 199

         (v) Acidity of hydrocarbons

         (a) Hydrogen exist on electronegative carbon is acidic in nature.

         (b) Acidity of hydrogen is directly proportional to the electronegativity of the atom on which hydrogen is present.

         Thus  

1638_applications of hybridisation4.png

         (c) Acidity of hydrocarbon    % of s-character

                                    

% s-character    50                   33.33                     25

                        25                   44                        50

         s- character and acidity in descending order

         Acidity 1573_applications of hybridisation5.png

         Order of acidic nature of alkynes is,

491_applications of hybridisation6.png

The relative acidic character takes the order;

1182_applications of hybridisation7.png

         Obviously, the basic character of their conjugate bases follows the reverse sequence, i.e.,

1754_applications of hybridisation8.png

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