Course Sidekick: Organic Chemistry I

Explore long line drawings in organic chemistry, learning how hydrocarbon chains like propane are represented with zigzag patterns, bonds, and hydrogens, including single, double, and triple bonds.

Master bond-line drawings by showing hydrogens on heteroatoms, drawing carbons with correct hydrogens, placing double bonds away from substituents, and recognizing changes by hydrogen counts.

Learn to identify formal charges by counting valence electrons and lone pairs around atoms, using propane and key elements like carbon, nitrogen, and oxygen.

Learn to infer lone pairs around atoms by combining valence electron counts from the periodic table with observed formal charges and bond counts, then draw in the lone pairs.

Learn to represent resonance structures by using curved arrows to show electron movement and brackets to display alternate electron arrangements in benzene and other molecules.

Apply resonance rules: never break a single bond; for second-row elements like C, N, O, F, bonds plus lone pairs total four, using arrow pushing to show valid electron movement.

Identify formal charges and practice drawing resonance structures by shifting electrons, checking overall charge, and recognizing how lone pairs and double bonds create positive or negative charges.

Identify five resonance patterns, including lone pair next to a pi bond, lone pair next to a positive charge, and pi bonds on a ring, through drawing practice.

Prioritize resonance structures by minimizing charges, favoring neutral forms for stability. Electronegative atoms like oxygen or nitrogen influence significance, limiting some positively charged arrangements.

Review orbital shapes and hybridization states to predict reactions and three-dimensional molecular geometry, using sp, sp2, and sp3 hybrids and the rule: bonds plus lone pairs equal hybrid orbitals.

Explore 3D molecular geometry with VSEPR theory to predict shapes from sp3, sp2, and sp hybridizations, including tetrahedral, trigonal pyramidal, bent, and linear arrangements, considering lone pairs.

Explore how acid-base strength relates to the stability of the conjugate base's negative charge, focusing on the atom with the charge and comparing electronegativity and size.

This lesson shows how resonance delocalizes a negative charge over oxygen atoms to stabilize a conjugate base. It compares two structures and notes induction as a forthcoming factor.

Explore induction as a factor in stabilizing negative charges, showing how electronegativity, resonance, and proximity influence acidity, alpha effects, and hyperconjugation in conjugate bases.

Examine how sp and sp2 hybridized orbitals influence acidity and equilibrium through conjugate bases and proton transfer. Apply four factors: atom charge, resonance, induction, and orbitals to predict reaction direction.

Use pKa values to gauge acidity; lower pKa means higher acidity and greater magnitude differences. Illustrate mechanisms with curved arrows moving electrons from base to proton, forming the conjugate base.

Explore IUPAC nomenclature in organic chemistry and the five parts of every name: stereoisomerism, substitutions, parent chain, unsaturation, and functional group, with a practical naming example.

Explore the six common functional groups and their naming suffixes, including carboxylic acid, ester, aldehyde, ketone, alcohol, and amine, with R group wildcards, substitutions, and priority.

Learn how to identify unsaturation in hydrocarbons, differentiate saturated and unsaturated compounds, and name double and triple bonded molecules using ene and yne suffixes and prefixes like di and tri.

Learn to name the parent chain in organic compounds, choosing the chain that includes the functional group and double or triple bonds, or the longest chain when none are present.

Explore the naming of substituents on a parent chain in organic chemistry, including methyl, ethyl, propyl, and isopropyl, their abbreviations and the yl ending, plus hydroxy and halogen substitutions.

Explore stereoisomerism in organic chemistry by naming compounds with fixed double bonds, and distinguish cis and trans configurations, noting when identical groups yield no stereo centers.

Learn to number the parent chain from the functional group, then from the double or triple bond if needed, assign lowest locants, and recognize common names and substitutions.

Learn how to visualize molecular conformations using Newman projections and chair forms, using wedges and dashes to distinguish front and back carbons, staggered and eclipsed states, and energy considerations.

Explore the relative stability of butane’s Nouman projections, comparing three staggered conformations—anti, gauche, and another—versus three eclipsed forms. Anti is lowest energy, eclipsed forms are higher due to crowding.

Learn to draw the chair conformation of cyclohexane, recognize axial and equatorial substituent positions, and practice parallel alignment of bonds for accurate chair drawings.

Learn how to draw substituents on a chair conformation, assign axial and equatorial positions, and understand ring flipping and reinflating to swap axial and equatorial substituents.

Predict the relative stability of chair conformations in cyclohexane derivatives by placing bulky groups in equatorial positions to minimize steric hindrance; understand chair flip and locking effects.

Explore stereocenters and configurations such as R and S, show how a carbon bonded to four different atoms becomes chiral, and link mirror-image relationships to enantiomers.

Learn how to determine the configuration of a stereocenter using atomic weight-based priority, assign numbers, rotate to place four on the dash, and distinguish R from S.

Explore how to name organic compounds by applying the five-part nomenclature, identify stereocenters and assign R/S configurations, and distinguish E/Z geometry for alkenes with priority rules.

Define enantiomers, diastereomers, and meso compounds as mirror-image, non-superimposable pairs and molecules with internal symmetry, and illustrate how wedge-to-dash flips and mirror drawings distinguish them.

Learn how to use Fischer projections for three stereocenters, converting line drawings by rotating bonds, with horizontal lines toward us and vertical lines away, and assign configurations by priority.

Learn how organic reaction mechanisms depict electron movement with curved arrows, covering lone-pair to bond, bond-to-lone-pair, bond-to-bond steps, and multistep mechanisms.

Identify short-lived intermediates and use arrow pushing to predict the next step, illustrated by hydroxide attack creating a negatively charged oxygen; future lessons compare nucleophiles and electrophiles.

Explore the differences between nucleophiles and electrophiles, how electron-rich nucleophiles attack electron-poor electrophiles, and how bases can act as nucleophiles with kinetic and equilibrium considerations.

Explore regiochemistry within reaction mechanisms, learn how a base attacks specific hydrogens to form the most substituted double bond, and compare competing pathways.

Explore how stereochemistry is shown within a mechanism, focusing on R and S configurations and anti- and syn-additions to predict final products.

Learn to build a three-component mechanism list, with reaction type, stereochemistry, and regiochemistry, by drawing SN2 inversion and SN1 substitution mechanisms with nucleophile attack, leaving group departure, and carbocation steps.

Explore substitution reactions, compare sn1 and sn2 mechanisms, and understand how nucleophile, leaving group, and stereochemistry-driven inversion influence rate and products.

Explore four factors: electrophile (substrate), leaving group, solvent, and nucleophile strength to decide SN1 versus SN2. Analyze primary, secondary, and tertiary substrates and how nucleophile strength shifts the reaction.

Analyze how leaving group quality (excellent, good, bad) and solvent choice (polar protic vs polar aprotic) influence SN1 and SN2 rates, with examples of proton-donating and non-donating solvents.

Apply the four factors—substrate structure, nucleophile strength, leaving group quality, and solvent—to predict SN1 or SN2 reactions, illustrated with primary, secondary, tertiary cases and DMSO.