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9701 · 13.3

Shapes of organic molecules; σ and π bonds flashcards

Revision flashcards for Cambridge 9701 Shapes of organic molecules; σ and π bonds (syllabus 13.3). Flip, recall, then mark a real past-paper question.

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    What is a σ (sigma) bond?

    A strong covalent bond formed by the direct, head-on overlap of atomic orbitals along the internuclear axis. All single covalent bonds are σ bonds.

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    What is a π (pi) bond?

    A covalent bond formed by the sideways overlap of adjacent, parallel p-orbitals, above and below the plane of the σ bond. It is weaker than a σ bond.

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    How are the electrons distributed in a σ bond?

    The electron density is concentrated on the line directly between the two bonded nuclei (the internuclear axis).

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    How are the electrons distributed in a π bond?

    The electron density is concentrated in two regions, one above and one below the plane of the nuclei.

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    What is the composition of a C=C double bond?

    One σ bond and one π bond.

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    What is the composition of a C≡C triple bond?

    One σ bond and two π bonds.

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    Why is there free rotation around a C-C single bond?

    Because it is a σ bond, which is symmetrical about the internuclear axis. Rotation does not break the orbital overlap.

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    Why is there no free rotation around a C=C double bond?

    Because rotation would break the sideways overlap of the p-orbitals that form the π bond, which requires a significant amount of energy.

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    What is the shape and bond angle around each carbon in ethane ($C_2H_6$)?

    Tetrahedral, with bond angles of approximately 109.5°. Each carbon has 4 bonding pairs and 0 lone pairs.

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    What is the shape and bond angle around each carbon in ethene ($C_2H_4$)?

    Trigonal planar, with bond angles of approximately 120°. Each carbon has 3 regions of electron density (2x C-H, 1x C=C).

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    Describe the geometry of a benzene ($C_6H_6$) molecule.

    It is a planar, regular hexagon. All C-C bond lengths are identical and all bond angles are 120°.

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    What is a delocalised π system?

    A system where π electrons are shared between more than two nuclei. In benzene, six p-orbitals overlap to form a continuous ring of electron density above and below the plane of the carbon atoms.