A study Guide For Organic Chemistry
Chapter 1
- The structural theory.
- Chemical bond and octet rule.
- Lewis structure.
- Exceptions to the octet rule.
- Representation of structural formulas, bond line, dash, 3-D.
Chapter 2
- Hydrocarbons: alkanes, alkenes,alkynes.
- Naming of alkyl groups. Functional groups and families of organic compounds.
- Physical properties and molecular structure.
Chapter 3
- Heterolysis cleavage of covalent bond.
- Acids and bases, strength of acids and bases: Ka and pKa.
- Predicting the outcome of acid-base reactions.
- The effect of electronegative atoms, inductive effects, and hybridization on acidity.
Chapter 4
- Constitutional isomers
- Naming alkanes, alkyl halides, alcohols, and cycloalkanes.
- Naming alkynes and alkenes.
- Physical properties of alkanes and cycloalkanes.
- Sigma bonds and bond rotation.
- Conformation stability of ethane (staggered-eclipsed).
- Conformation of butane.(anti-eclipsed-gauche)
- Conformation of cyclohexane (boat, chair)(ring strain).
- Axial and equatorial substitution on cycloalkanes and their relative stability.
Chapter 5
- Constitutional isomers, diastereomers, enantiomers, chiral, achiral, meso compounds.
- The biological importance of chirality.
- Naming compounds with more than one stereocenter.
- Fischer projection formula.
- Stereoisomerism of cyclic compounds and their derivatives.
Chapter 6
- Mechanisms of recations: addition, elimination, substitution, and rearrangement..
- Cleavage of double bonds, carbocations and carboanions.
- Nucleophilic substitution reactions of alkyl halides: nucleophiles, leaving groups.
- Sn2 mechanism (energy diagram, transition state, and intermediate).
- Stereochemistry of Sn2.
- SN1 mechanism.
- Structure of carbocation, relative stability of carbocations.
- Stereochemistry of Sn1.
- Factors that affect Sn1, Sn2.
- Organic synthesis using Sn2 and Sn1.
- E2 and E1 mechanisms
- Substitution vs. elemination
Chapter 7
- Naming of alkenes and cycloalkenes, cis-trans and E-Z system.
- Naming of alkynes.
- Relative stability of alkenes.
- Cycloalkenes.
- Synthesis of alkenes and Zaitsev's rule.
- Stability of carbocations and molecular rearrangements.
- Synyhesis of alkynes.
- Acidity of terminal alkynes and their reactions.
- Hydrogenation of alkenes and alkynes.
- Syn-anti additions to alkenes and alkynes.
Chapter 8
- Aditions to alkenes; HX, H2SO4, H2O, X2 (Markovnikov's rule).
- Addition of HX and X2 to alkynes.
- Oxidative cleavage of alkynes.
Chapter 10
- Radical reactions.
- Homolytic bond dissociation energies and relative stability of radicals.
- Reaction of alkanes with halogens (chain reaction).
- Halogenation of higher alkanes (selectivity of bromine).
- Stereochemistry of halogenation.
- Radical addition to alkenes (anti-Markovnikov).
- Radical polymerization of alkenes.
- Other important radical chain reactions (autoxidation, ozone depletion).
Chapter 11
- Naming of alcohols, phenols, and ethers.
- Properties of alcohols and ethers, the H-bond.
- Synthesis of alcohols, from alkenes, and carbonyl compounds.
- Reactions of alcohols (the acidity of alcohols).
- Alkyl phosphates and alkyl halides from alcohols.
- Synthesis of ethers.
- Reactions of ethers.
- Epoxides, the reaction of epoxides by ring opening.
- Anti hydroxylation of alkenes via epoxides.
Chapter 13
- Conjugated dienes and allylic substitution.
- Stability of allylic radical and carbocation, resonance structure.
- Drawing of resonance structures and their stability.
- Alkadienes and addition reactions of dienes.
- The Diels-Alder reaction.
Chapter 14&15
- Structure and stability of benzene ring, meaning of aromaticity.
- Naming aromatic compounds.
- Reactions of aromatic compounds (electrophilic aromatic substitution):
- Halogenation
- Nitration
- Sulfonation
- Friedel-crafts alkylation and acylation.
- Orientation of reactions on substituted aromatic rings.
- Oxidation and reduction of aromatic rings.
- Organic synthesis.
Chapter 16
- Nomenclature of aldehydes and ketones.
- Synthesis of aldehydes and ketones.
- Nucleophilic addition to the carbon-oxygen double bond:
- water addition (gem-diols)
- alcohol addition (acetal, hemiacetal and ketal, hemiketal)
- Oxidation of aldehydes and ketones.
Chapter 18
- Nomenclature of carboxylic acids.
- Why carboxylic acids are more acidic than alcohols.
- The conductive effect on acidity.
- Preparation of carboxylic acids.
- Synthesis and reactions of carboxylic acid derivatives. ( acyl chloride, acid anhydride, ester, amide).
- Decarboxylation of carboxylic acids.
Chapter 20
- Nomenclature of amines, arylamines, and heterocyclic amines.
- Basicity of amines.
- Preparation of amines: - Nucleophilic substitution.
- Reduction of Nitro and amide compounds.
- Reduction of aldehydes and ketones.
- Reactions of amines: - as nucleophiles.
- reaction with nitrous acid (HNO2) to form nitroso compounds.