Organic Chemistry — Structure, Bonding & Nomenclature flashcards
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Hybridization, resonance, formal charge, intermolecular forces, functional-group priority, IUPAC naming, E/Z and R/S, degrees of unsaturation, Newman and chair conformations, stereoisomer types, optical activity and Fischer projections.
Learn deck · part of Organic Chemistry I/II · written against: Standard two-semester sequence; compound names use either the traditional locant style (1-butene, 2-propanol) or the IUPAC 2013 style (but-1-ene, propan-2-ol), both in wide use, and the nomenclature cards teach the 2013 rule. Updated 2026-10-10.
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What is the quickest way to assign the hybridization of a carbon, and what geometry and bond angle go with each result?Count the groups around it (bonded atoms plus lone pairs): 4 groups → sp³, tetrahedral, 109.5°; 3 groups → sp², trigonal planar, 120°; 2 groups → sp, linear, 180°. Equivalently, for a neutral carbon with four bonds, each π bond on the carbon removes one p orbital from the hybrid set.Hybridization & Geometry
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What may you move, and what may you never do, when drawing resonance structures?Move only π electrons and lone pairs; nuclei never move, the total electron count and net charge stay the same, and no second-row atom may exceed an octet. The structures are not equilibrating isomers — the real molecule is a single weighted hybrid.Resonance
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Carbon tetrachloride has four strongly polar C–Cl bonds yet no dipole moment. Why?Its tetrahedral symmetry makes the four bond dipoles cancel as vectors, so the net dipole is zero. Breaking the symmetry — as in chloroform, CHCl₃ — leaves a net dipole and a polar molecule.Polarity & Intermolecular Forces
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Structurally, what separates an ester from an ether, and how does each show up in a name?An ester is R–C(=O)–O–R', a carbonyl attached to an O–R'; an ether is R–O–R' with no carbonyl. Esters are named 'alkyl alkanoate' (ethyl acetate); ethers as 'alkyl alkyl ether' or with an alkoxy prefix (methoxyethane).Functional Groups
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How do you choose and number the parent chain of an acyclic compound?Take the longest continuous chain that contains the principal functional group and as many multiple bonds as possible; on a tie, take the chain with more substituents. Number from the end that gives the lowest locant to the principal group, then to the first multiple bond, then to the first substituent.IUPAC Nomenclature
Watch out: the 2013 IUPAC recommendations put chain length before the number of multiple bonds; many textbooks still teach the older rule that the chain must include them. -
What is the formula for degrees of unsaturation, and how are N, O and halogens handled?. Oxygen is ignored, each halogen counts like a hydrogen, and each nitrogen adds one to the numerator. Every ring or π bond is one degree; a benzene ring is four.Degrees of Unsaturation
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Looking down the C2–C3 bond of butane, list its conformations from lowest to highest energy with approximate energies.Anti (methyls 180° apart, 0) < gauche (60° apart, about 3.8 kJ/mol) < eclipsed methyl/H (about 16 kJ/mol) < fully eclipsed methyl/methyl (roughly 19–25 kJ/mol). Staggered forms are minima; eclipsed forms are the barriers between them.Newman Projections & Conformations
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What happens to axial and equatorial substituents when a cyclohexane chair flips, and what does not change?Every axial position becomes equatorial and vice versa. The cis/trans relationships do not change — a group that was 'up' stays up — because the flip is a conformational change, not a bond-breaking one.Cyclohexane Chairs
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How is specific rotation defined, and does its sign tell you R or S?, with the observed rotation α in degrees, concentration c in g/mL and path length l in decimeters. (+) is dextrorotatory, (−) levorotatory, and the sign has no fixed relationship to R or S — it must be measured.Optical Activity
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In a Fischer projection, which bonds point toward you and which away, and how is the chain oriented?Horizontal bonds come toward the viewer; vertical bonds go away, and each intersection is a carbon. The main chain runs vertically with C1, usually the most oxidized carbon, at the top.Fischer Projections
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About these cards
Review status: Second-reader reviewed, with corrections applied.
Checked against:
- OpenStax Organic Chemistry: A Tenth Edition, consulted as a reference; no text copied.
- Checked against IUPAC Nomenclature of Organic Chemistry (2013 Recommendations) for naming rules — reference only; no text copied.
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