9: Introduction to Organic Chemistry
- Page ID
- 341931
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)- 9.1: Why Is Organic Chemistry Special?
- One very important factor that make so much of chemistry center on a single element is that carbon-carbon bonds are strong, so long chains or rings of bonded carbon atoms are possible. Carbon is not unique in forming bonds to itself because other elements such as boron, silicon, and phosphorus form strong bonds in the elementary state. The uniqueness of carbon stems more from the fact that it forms strong carbon-carbon bonds that also are strong when in combination with other elements.
- 9.2: sp³ Hybrid Orbitals and the Structure of Methane
- The four identical C-H single bonds in methane form as the result of sigma bond overlap between the sp3 hybrid orbitals of carbon and the s orbital of each hydrogen.
- 9.3: sp² Hybrid Orbitals and the Structure of Ethylene
- The C=C bond in ethylene forms as the result of both a sigma bond overlap between a sp2 hybrid orbital on each carbon and a pi bond overlap of a p orbital on each carbon
- 9.4: sp Hybrid Orbitals and the Structure of Acetylene
- The carbon-carbon triple bond in acetylene forms as the result of one sigma bond overlap between a sp hybrid orbital on each carbon and two pi bond overlaps of p orbitals on each carbon.
- 9.5: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
- The atomic orbitals of nitrogen, oxygen, phosphorus and sulfur can hybridize in the same way as those of carbon.
- 9.6: Describing Chemical Bonds- Molecular Orbital Theory
- Molecular Orbital theory (MO) is a more advanced bonding model than Valence Bond Theory, in which two atomic orbitals overlap to form two molecular orbitals – a bonding MO and an anti-bonding MO.
- 9.7: Lone Pair Electrons and Bonding Theories
- The chemical reactivity of lone pair electrons can be determined from the identity of the orbital they occupy. This concept will be further refined when we study aromaticity.
- 9.8: Drawing Chemical Structures
- Kekulé Formulas or structural formulas display the atoms of the molecule in the order they are bonded. Condensed structural formulas show the order of atoms like a structural formula but are written in a single line to save space. Skeleton formulas or Shorthand formulas or line-angle formulas are used to write carbon and hydrogen atoms more efficiently by replacing the letters with lines. Isomers have the same molecular formula, but different structural formulas
- 9.9: A Review of Isomerism
- Isomers are molecules which contain the same number and type of atoms, but with different arrangements. The arrangement can be different due to the order the atoms are bonded together or due to their arrangement in space.
- 9.10: Enantiomers and the Tetrahedral Carbon
- A classification within isomerism is whether two isomers are superimposable mirror-images of each other. This can have an impact on reactivity and an important effect on organic molecules.
- 9.11: Polar Covalent Bonds - Dipole Moments
- Mathematically, dipole moments are vectors; they possess both a magnitude and a direction. The dipole moment of a molecule is therefore the vector sum of the dipole moments of the individual bonds in the molecule. If the individual bond dipole moments cancel one another, there is no net dipole moment.
- 9.12: Organic Acids and Organic Bases
- In the absence of pKa values, the relative strength of an organic acid can be predicted based on the stability of the conjugate base that it forms. The acid that forms the more stable conjugate base will be the stronger acid. The common factors that affect the conjugate base's stability are 1) the size and electronegativity of the the atom that has lost the proton, 2) resonance effects, 3) inductive effects, and 4) solvation effects.
- 9.13: Noncovalent Interactions Between Molecules
- In contrast to intramolecular forces, such as the covalent bonds that hold atoms together in molecules and polyatomic ions, intermolecular forces hold molecules together in a liquid or solid. Intermolecular forces are generally much weaker than covalent bonds. The most common intermolecular forces in organic chemistry are from strongest to weakest are hydrogen bonds, dipole-dipole interactions, and London Dispersion (van der Waals) forces.