Eresorganic
– an online resource for students of Introductory Organic Chemistry CHEM2401

eResorganic is a series of audio-linked sketches prepared using a tablet: click, watch, listen and learn as often as you wish.

Click on the page numbers to access the following topics: this page - Functional groups and nomenclature; Page 2 – Structures, bonding and acidity; Page 3 – Isomerism; Page 4 – Organic reactions; Page 5 – Characterization

Naïve individuals might mistake the use of this resource as an alternative to regular attendance at lectures: do not make this mistake.

Adobe flashplayer (http://get.adobe.com/flashplayer) might need updating on your computer for you to see/hear these sketches.

Functional groups and nomenclature (both self-taught)

These topics are both self-taught and will not be covered extensively in lectures. The OWL/Blackboard site has additional material regarding how to draw and name organic molecules (see Course Content/Study Resources/Additional Material), as does the text-book.

Drawing and identifying functional groups - basics

Drawing and identifying functional groups - single bonds

Drawing and identifying functional groups - double bonds

Drawing and identifying functional groups - triple bonds

Primary (1^o), secondary (2^o) and tertiary (3^o) alkyl halides and alcohols

Primary (1^o), secondary (2^o) and tertiary (3^o) amines

Functional groups in complex molecules

Nomenclature - see Bb and text-book

Structures, bonding and acidity

Lewis structures - octet rule

Formal charges

Exceptions to the octet rule

Contributing resonance structures

Electron-pushing using curly arrows

Disallowed curly arrow-pushing

Resonance structures - examples

Rules for drawing Lewis structures

VSEPR (valence shell electron pair repulsion theory) – summary

MO theory – basics and LCAO 

Hybridization - sp³

Hybridization - sp²

Hybridization - sp

Drawing and labeling Lewis structures - putting it all together

Allylic and benzylic systems

Acids and bases - pushing curly/curved arrows

Conjugate acids and bases - best acid wins

Factors affecting pK_a values - stability of conjugate bases

pK_a values - numbers and trends

Ranking acids and bases

Isomerism

Isomerism - overview

Alkanes - drawing molecules

Conformational isomers of alkanes – Newman projections (circles and sticks)

Cycloalkanes

Drawing chair conformations of cyclohexanes – parallel lines

Chair conformations as Newman projections

Conformational isomers of cyclohexanes – the ring flip

Upside-down cyclohexane chairs

Stereochemistry

Chiral and achiral - optical activity

Enantiomers

Assigning Cahn-Ingold-Prelog priorities

Applying Cahn-Ingold-Prelog rules – deducing R and S, E and Z

Diastereomers

Meso compounds

Fischer projections – criss-cross

Erythrose and threose

Preparation of homochiral molecules

Resolution of enantiomers

Flow-chart for deducing isomeric relationships

Organic reactions

Substitution reactions

S_N2 reactions - bimolecular substitution

Rates of S_N2 reactions

Mechanism of S_N2 reactions

Reaction profile of S_N2 reactions (reaction coordinate diagram)

Inversion of configuration in S_N2 reactions

Electrophiles in S_N2 reactions (methyl, primary, secondary and tertiary)

Nucleophiles in S_N2 reactions

Leaving groups in S_N2 reactions

Solvent effects in S_N2 reactions

Equilibrium in S_N2 reactions

S_N1 reactions – unimolecular substitution

Rate and mechanism of S_N1 reactions

Reaction profile of S_N1 reactions (reaction coordinate diagram)

Stereochemistry of S_N1 reactions

S_N1 reactions and rearrangements

Summary of S_N1 and S_N2 reactions

Elimination reactions

Mechanism, rate and reaction profile of E2 reactions

Stereospecificity of E2 reactions

Stereoselectivity of E2 reactions

Regioselectivity of E2 reactions

E1 reactions

Comparison of S_N1, S_N2, E1 and E2 reactions

Reactions of alkenes

Hydrogenation reactions (alkenes)

Reactions with bromine and chlorine

Addition of HX across double bonds

Oxymercuration-demercuration reactions

Epoxidation reactions with m-CPBA

Dihydroxylation reactions

Oxidative cleavage of alkenes

Hydroboration-oxidation of alkenes

Reactions of alkynes

Alkylation

Hydrogenation reactions (alkynes)

Reduction of alkynes

Additions across triple bonds

Hydroboration-oxidation of alkynes

Synthesis of methyl ketones

Synthetic sequences

Characterization

Elements of unsaturation – double bond equivalents

Mass spectrometry

Basics of mass spectrometry – what the lines correspond to

Odd molecular masses – molecules containing one nitrogen atom

Isotope patterns – carbon-13

Isotope patterns – molecules containing bromine and chlorine atoms

Deducing potential formulae using mass spectral information

NMR spectroscopy – theory in brief

Acquiring NMR data – solvents, references and experiments

Chemical shifts – shielding and spectroscopy data tables

Clues in ¹H NMR spectra – integration and symmetry

Multiplicity in ¹H NMR spectroscopy – three-bond H-C-C-H coupling

Pascal's triangle – lines and patterns

Exchangeable protons

Seven ¹H NMR spectra – deducing structures

Differences in ¹³C NMR spectroscopy – one-bond C-H coupling

Deducing structures using mass spectrometry and NMR spectroscopy

Example 1 – Compound 6 (MS and NMR)

Example 2 – Compound 28 (MS and NMR)

Example 3 – Compound X (MS and NMR)

Example 4 – Compound Y (MS and NMR)

Example 5 – Compound Z (MS and NMR)