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Flashcards in this deck (24)

Ricerca in corso...
  • How is an sp² hybrid orbital formed in carbon?


    Combination of the 2s orbital with two 2p orbitals to give three sp² hybrid orbitals.

    chemistry hybridization
  • What is the molecular geometry of an sp²-hybridized carbon and its bond angles?


    Trigonal planar geometry with bond angles of approximately \(120^\circ\).

    geometry hybridization
  • Where is the remaining unhybridized p orbital located in an sp² carbon?


    Perpendicular to the plane of the three sp² orbitals.

    structure orbitals
  • What two types of bonds make up a carbon-carbon double bond (C=C)?


    One sigma bond from sp²–sp² overlap and one pi bond from side-by-side 2p–2p overlap.

    bonding alkenes
  • How does the C=C bond length compare to a C–C single bond as noted in the study notes?


    The C=C bond is shorter, about \(134\text{ pm}\).

    bondlength alkenes
  • What effect does the pi bond in a C=C double bond have on rotation about the bond?


    The pi bond restricts rotation around the C=C bond.

    stereochemistry alkenes
  • Describe the spatial arrangement of sp² orbitals relative to each other.


    Three sp² orbitals lie in one plane and are separated by approximately \(120^\circ\) from each other.

    orbitals chemistry
  • What type of bond forms when two sp²-hybridized orbitals overlap?


    • A sigma (σ) bond
    hybridization sigma bonding
  • How is a pi (π) bond formed between carbon atoms in sp² systems?


    • By side-to-side overlap of p orbitals (2p–2p overlap)
    pi bonding orbitals
  • What bonds make up a carbon–carbon double bond in sp²-hybridized carbons?


    • One sp²–sp² σ bond
    • One 2p–2p π bond
    doublebond sigma pi
  • Where are the electrons of a σ bond located relative to the nuclei?


    • Centered between the two nuclei
    sigma electrons
  • Where do electrons in a π bond reside relative to the line between nuclei?


    • In regions on either side of the line between the nuclei
    pi electrons
  • Provide two geometric or bonding properties of sp²-hybridized carbon in a C=C double bond.


    • Trigonal planar geometry, \(120^\circ\)
    • C=C has one σ and one π bond (shorter bond length, restricts rotation)
    geometry sp2 doublebond
  • Show an illustrative diagram of sp² orbital σ overlap and p-orbital π overlap for a C=C bond.


    Diagram of sp² σ overlap and p-orbital π overlap - Caption: sp² orbitals form the σ bond; p orbitals form the π bond

    diagram visual bonding
  • What orbitals form σ bonds to hydrogen in ethylene (C₂H₄)?


    Hydrogen atoms form σ bonds with four sp² orbitals.

    bonding hybridization ethylene
  • What are the approximate H–C–H and H–C–C bond angles in ethylene?


    Both H–C–H and H–C–C bond angles are about 120°.

    geometry ethylene angles
  • How does the C=C double bond in ethylene compare to a C–C single bond in ethane?


    The C=C double bond in ethylene is shorter and stronger than the C–C single bond in ethane.

    bonding comparison ethylene
  • What is the bond length of the C=C double bond in ethylene and the C–C single bond value given?


    • C=C (ethylene): 134 pm
    • C–C (single): 154 pm
    bond-length ethylene values
  • Where can a structural diagram of ethylene showing bond angles and bond lengths be found?


    See molecular model and structural diagrams: Molecular model of ethylene

    image diagram ethylene
  • What molecule is titled in the section 'Structure of Ethylene'?


    Ethylene (C₂H₄)

    chemistry organic molecules
  • Write the Lewis structure shown for ethylene in the text.


    H:C::C:H (each carbon bonded to two H and to the other C)

    chemistry lewis bonding
  • What is the molecular shape of a molecule with a carbon–carbon double bond as given?


    Trigonal planar

    chemistry geometry bonding
  • Which atoms form the vertices of the triangle in the ethylene shape?


    The hydrogens and carbons

    chemistry geometry structure
  • What are the bond angles in the ethylene molecule as stated?


    120°

    chemistry angles structure
Appunti di studio

sp\(^2\) Hybridization (core idea)

  • Definition: sp\(^2\) hybridization mixes one 2s and two 2p orbitals to give three equivalent sp\(^2\) orbitals and one unhybridized 2p orbital.
  • Geometry: The three sp\(^2\) orbitals lie in a plane with trigonal planar geometry and bond angles of \(120^\circ\).
  • Unhybridized p orbital: The remaining 2p orbital is perpendicular to the sp\(^2\) plane and can overlap with another p orbital to form a \(\pi\) bond.

sp² orbitals side and top views

Sigma (\(\sigma\)) and Pi (\(\pi\)) Bonds

  • Sigma bond (\(\sigma\)): Formed by end-to-end (head-on) overlap of two sp\(^2\) orbitals; electron density is centered along the internuclear axis.
  • Pi bond (\(\pi\)): Formed by side-to-side overlap of the unhybridized 2p orbitals; electron density lies above and below the molecular plane.
  • Double bond composition: A carbon–carbon double bond consists of one \(\sigma\) bond (sp\(^2\)–sp\(^2\)) plus one \(\pi\) bond (2p–2p), sharing four electrons total.

sp² overlap forming σ and π bonds

Structure and Properties of Ethylene (C₂H₄)

  • Bonding arrangement: Each carbon is sp\(^2\)-hybridized; two sp\(^2\) orbitals form C–H bonds and the third forms the C–C \(\sigma\) bond.
  • Geometry: At each carbon the atoms are arranged trigonal-planar; H–C–H and H–C–C angles ≈ \(120^\circ\).
  • Bond lengths: C=C double bond is shorter and stronger than a C–C single bond; typical values: C=C ≈ \(134\text{ pm}\), C–C (single) ≈ \(154\text{ pm}\).
  • Restricted rotation: The \(\pi\) bond fixes the relative positions of groups on the two carbons, preventing free rotation about the C=C bond.

Ethylene molecular model and bond measurements

Lewis Structure and Molecular Shape

  • Lewis: H:C::C:H with each carbon forming three sigma bonds and one pi bond (one C–C \(\sigma\), one C=C \(\pi\)).
  • Shape: Hydrogens and carbons occupy the vertices of triangles around each carbon (trigonal planar), shown by bond-angle diagrams.

Lewis structure and trigonal planar shape

Key Consequences & Practical Points

  • Reactivity: The \(\pi\) electrons are more exposed (above/below the plane) and are typically the site of electrophilic attack.
  • Bond strength vs. length: Shorter bonds (C=C) generally have higher bond energies than single bonds; the \(\pi\) component is weaker than the \(\sigma\) component.
  • Stereochemistry: Planarity of sp\(^2\) carbons is essential for cis/trans (E/Z) isomerism in substituted alkenes.

Mnemonics & Quick Memory Aids

  • "sp\(^2\) = planar, pair (one) p left over" — three orbitals in plane, one perpendicular p.
  • Double bond = 1 \sigma (strong, axis) + 1 \pi (weaker, above/below).

Quick Practice Questions

  1. Why does an sp\(^2\) carbon have \(120^\circ\) bond angles? (Answer: three equivalent sp\(^2\) orbitals arrange to minimize repulsion → trigonal planar.)
  2. What prevents rotation about a C=C bond? (Answer: the \(\pi\) bond requires overlap of perpendicular p orbitals.)
  3. Compare bond lengths: which is longer, C–C single or C=C double? (Answer: C–C single ≈ \(154\text{ pm}\), C=C ≈ \(134\text{ pm}\).)