Acrylonitrile is the building block of the synthetic fiber...

Acrylonitrile is the building block of the synthetic fiber Orlon.
(a) Which carbon-carbon bond is shorter?
(b) Which carbon-carbon bond is stronger?
(c) Which bond is the most polar? What is the partial negative end of that bond?

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Key Concepts

Hybridization

The hybridization state of a carbon atom influences its bond length and strength. For instance, an sp-hybridized carbon (with 50% s-character) will form shorter, stronger bonds than an sp2-hybridized carbon (with about 33% s-character) due to the greater proportion of s-character leading to electrons being held more closely to the nucleus.

Bond Order

Bond order refers to the number of bonding interactions between two atoms. A double bond (bond order of 2) exhibits both a sigma and a pi bond, making it generally stronger and shorter than a single bond (bond order of 1), because the additional bonding electron density enhances orbital overlap.

Electronegativity and Bond Polarity

Differences in electronegativity between bonded atoms cause unequal sharing of electrons, resulting in polar bonds. In bonds where one atom is significantly more electronegative than the other, that atom attains a partial negative charge, which is key to understanding the polarity and reactivity of the bond.

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