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OAT Orgo Day One
| Question | Answer |
|---|---|
| What is the difference between molecular formula, condensed formula, and structural formula? | Molecular formula: shows number of atoms of each element (e.g., C₅H₁₂) Condensed formula: shows order of attachment (e.g., CH₃CH₂CH₂CH₂CH₃) Structural formula: shows all bonds between atoms |
| What do wedge and dashed bonds represent? | Wedge bonds = atoms coming out of the page toward viewer; Dashed bonds = atoms going into the page away from viewer |
| What are constitutional (structural) isomers? | Compounds with the same molecular formula but different connectivity of atoms |
| What is the steric number and how does it relate to hybridization? | Steric number = number of electron domains (lone pairs + bonds). It determines hybridization: 4 = sp³, 3 = sp², 2 = sp |
| What is the s-character and p-character of sp³, sp², and sp orbitals? | sp³: 25% s, 75% p sp²: 33% s, 67% p sp: 50% s, 50% p |
| Do cations and radicals contribute to steric number? | No. Cations have an empty unhybridized p orbital and radicals have a single unpaired electron in an unhybridized p orbital |
| What molecular geometry corresponds to each hybridization? | sp³ (4 bonds, 0 LP): tetrahedral, 109.5° sp³ (3 bonds, 1 LP): trigonal pyramidal, <109.5° sp³ (2 bonds, 2 LP): bent, <109.5° sp² (3 bonds, 0 LP): trigonal planar, 120° sp² (2 bonds, 1 LP): bent, <120° sp (2 bonds, 0 LP): linear, 180° |
| What is the difference between sigma and pi bonds? | Sigma (σ) bonds form from direct overlap of s orbitals and/or hybrid orbitals. Pi (π) bonds form from lateral overlap of unhybridized p orbitals |
| How many sigma and pi bonds are in single, double, and triple bonds? | Single bond: 1 σ Double bond: 1 σ + 1 π Triple bond: 1 σ + 2 π |
| What are the requirements for valid resonance structures? | Same skeleton (no atom movement) Valid Lewis structure Same net charge |
| What rules determine the most significant resonance contributor? | Maximize complete octets Minimize formal charges Negative charge on more electronegative atom is more stable Positive charge on less electronegative atom is more stable |
| How does resonance affect hybridization? | If an atom's lone pair electrons are delocalized through resonance, they don't contribute to the atom's steric number |
| What are the Brønsted-Lowry definitions of acids and bases? | Brønsted-Lowry acid = proton donor; Brønsted-Lowry base = proton acceptor |
| What are the Lewis definitions of acids and bases? | Lewis acid = electron pair acceptor; Lewis base = electron pair donor |
| How do Ka and pKa relate to acid strength? | Strong acid = high Ka, low pKa. Weak acid = low Ka, high pKa. (Ka and pKa are inversely related) |
| What does a compound's pKa measure? | The stability of the compound's conjugate base. Lower pKa = more stable conjugate base = stronger acid |
| Which direction does acid-base equilibrium favor? | Equilibrium favors formation of the weaker acid (higher pKa) |
| What does the CARDIO acronym stand for in ranking acidity? | Charge, Atom, Resonance delocalization, Induction, Orbital hybridization |
| How does charge affect acidity? | Acidity increases with increasing positive charge. H₃O⁺ > H₂O > OH⁻ |
| How does atom position on the periodic table affect acidity? | Acidity increases going down a column (larger atomic radius) and left to right across a row (increasing electronegativity) |
| How does resonance delocalization affect acidity? | Resonance that stabilizes the conjugate base increases acidity. Acetic acid > ethanol because acetate is resonance-stabilized |
| How do inductive effects affect acidity? | Electronegative atoms on nearby carbons stabilize the conjugate base by pulling electron density, increasing acidity. CF₃COOH > CH₃COOH |
| How does orbital hybridization affect acidity? | Greater s-character = more stable negative charge (closer to nucleus). Terminal alkynes (sp) > alkenes (sp²) > alkanes (sp³) |
| What are the four types of IMFs from weakest to strongest? | London dispersion forces < dipole-dipole interactions < hydrogen bonding < ion-ion interactions |
| What are London dispersion forces? | Weakest IMF, occur between all molecules, arise from momentary dipoles. Only attractive force for non-polar molecules |
| When does hydrogen bonding occur? | When H is directly bonded to F, O, or N (highly electronegative elements) |
| What is the "like dissolves like" principle? | Compounds dissolve best in solvents with similar chemical properties and that participate in the same IMFs |
| How does hydrocarbon chain length affect water solubility? | Shorter hydrocarbon chains = higher water solubility (less hydrophobic region) |
| How do IMF strength and molecular size affect melting/boiling points? | Stronger IMFs = higher melting/boiling points. Larger molecules = higher melting/boiling points (more surface area for Van der Waals) |
| How does branching affect boiling point? | Increased branching decreases boiling point (less surface area, weaker intermolecular interactions) |
| How does branching and symmetry affect melting point? | Generally, branching decreases melting point. However, increased molecular symmetry increases melting point (tighter crystal packing) |
| What do double-headed and single-headed arrows represent? | Double-headed arrows = movement of two electrons (electron pair). Single-headed arrows = movement of one electron (radical) |
| Where can arrows originate and what does each mean? | Arrow from bond: movement of electrons in that bond (bond breakage) Arrow from atom: movement of lone pair or single electron from that atom (new bond formation) |
| What must remain constant during arrow-pushing? | Overall charge must stay the same (though charges on individual atoms may change) |
Created by:
smurtab