ORGANIC CHEMISTRY I CHEM 2323

COURSE DESCRIPTION (catalog description)

CHEM 2323 Organic Chemistry I (4-0-3) A study of the general principles of the chemistry of carbon. Topics include alkanes, alkynes, ethers, alcohols, stereochemistry, reactions, synthesis, and mechanisms. Prerequisite: CHEM 1305 and CHEM 1105 or CHEM 1312 and CHEM 1112.

REQUIRED TEXT/MANUALS

Organic Chemistry - Morrison and Boyd (latest edition)

Organic Chemistry Laboratory Procedures- Wheet (latest edition)

COURSE OUTLINE (content)

Structure and Properties

• Organic chemistry
• The structural theory
• The chemical bond before 1926
• Quantum mechanics
• Covalence numbers
• Atomic orbitals
• Electronic configuration. Pauli exclusion principle
• Molecular orbitals
• The covalent bond
• Hybrid orbitals:
  • Hybrid orbitals: sp
  • Hybrid orbitals: sp²
  • Hybrid orbitals: sp³
• Unshared pairs of electrons
• Intramolecular forces
• Bond dissociation energy. Homolysis and heterolysis
• Polarity of bonds
• Polarity of molecules
• Structure and physical properties
• Melting point
• Intermolecular forces
• Boiling point
• Solubility
• Isomerism

Methane Energy of Activation. Transition State

• Hydrocarbons
• Structure of methane
• Physical properties
• Source
• Reactions
• Oxidation, Heat of combustion
• Chlorination: a substitution reaction
• Control of chlorination
• Reaction with other halogens: halogenation
• Relative reactivity
• Reaction mechanisms
• Mechanism of chlorination. Free radicals
• Chain reactions
• Inhibitors
• Heat of reaction
• Energy of activation

Alkanes. Free-Radical Substitution

• Classification by structure: the family
• Structure of ethane
• Free rotation about the carbon-carbon single bond
• Conformations. Torsional strain
• Propane and the butanes
• Conformations of n-butane. Van der Waals repulsion
• Higher alkanes. The homologous series
• Nomenclature
• Alkyl groups
• Common names of alkanes
• IUPAC names of alkanes
• Classes of carbon atoms and hydrogen atoms
• Physical properties
• Industrial source
• Industrial source vs. laboratory preparation
• Preparation
• Reactions
• Halogenation
• Mechanism of halogenation
• Orientation of halogenation
• Relative reactivities of alkanes toward halogenation
• Ease of abstraction of hydrogen atoms. Energy of activation
• Stability of free radicals
• Ease of formation of free radicals
• Transition state for halogenation
• Orientation and reactivity
• Reactivity and selectivity
• Non-rearrangement of free radicals. Isotopic tracers
• Combustion
• Pyrolysis: cracking
• Determination of structure
• Analysis of alkanes

Review for Test 1 - Structure and Properties, Methane, and Alkane

Stereochemistry I. Stereoisomers

• Stereochemistry and stereoisomerism
• Isomer number and tetrahedral carbon
• Optical activity. Plane-polarized light
• The polarimeter
• Specific rotation
• Enantionmerism: the discovery
• Enantiomerism and tetrahedral carbon
• Enantiomerism and optical activity
• Prediction of enantiomerism. Chirality
• The chiral center
• Enantiomers
• The racemic modification
• Optical activity: a closer look
• Configuration
• Specification of configuration: R and S
• Sequence rules
• Diastereomers
• Meso Structures
• Specification of configuration: more than one chiral center
• Conformational isomers

Alkyl Halides Nucleophilic Aliphatic Substitution

• Homolytic and heterolytic chemistry
• Relative rates of competing reactions
• Structure. The functional group
• Classification
• Nomenclature
• Physical properties
• Preparation
  • from alcohols
  • halogenation of hydrocarbons
  • addition of hydrogen halide
  • addition of halogens to alkenes
  • addition of halogens to alkynes
  • halide exchange
• Reactions. Nucleophilic aliphatic substitution
• Reactions of Alkyl Halides
  • nucleophilic substitution
  • dehydrohalogenation
  • Grignard reagent
• Nucleophilic aliphatic substitution. Nucleophiles and leaving groups
• Rate of reaction: effect of concentration. Kinetics.
• Kinetics of nucleophilic aliphatic substitution. Second-order and first-order reactions
• Nucleophilic aliphatic substitution:duality of mechanisms
• The S_N2 reaction: mechanism and kinetics
• The S_N2 reaction: stereochemistry, Inversion of configuration
• The S_N2 reaction: reactivity. Steric hindrance
• The S_N1 reaction: mechanism and kinetics. Rate-determining step
• Carbocations
• Structure of carbocations
• The S_N1 reactions: stereochemistry
• Relative stabilities of carbocations
• Stabilization of carbocations. Accommodation of charge.
• Polar effects.
• The S_N1 reaction: reactivity. Ease of formation of carbocations
• Rearrangement of carbocations
• S_N2 vs. S_N1
• Analysis of alkyl halides

Alcohols

• Introduction
• Structure of alcohols
• Classification of alcohols
• Nomenclature of alcohols
  • common
  • iupac
• Physical properties of alcohols
• Industrial source
  • hydration of alkenes
  • oxo process
  • Fermentation of carbohydrates
• Fuel from carbohydrates. Carbon dioxide balance
• Ethanol
• Preparation of alcohol
  • hydrolysis of alkyl halides
  • grignard synthesis
• Reactions of alcohol
  • reaction with hydrogen halide
  • reaction with phosphorus trihalides
  • dehydration
  • reaction as acids
  • ester formation
  • oxidation of primary alcohol
  • oxidation of secondary alcohol
  • oxidation of ternary alcohol
• Alcohols as acids and bases
• Reaction of alcohols with hydrogen halides. Acid catalysis
• Formation of alkyl sulfonates
• Oxidation of alcohols

Ethers

• Structure
• Nomenclature of ethers
  • common
  • iupac
• Physical properties of ethers
• Industrial sources of ethers. Dehydration of alcohols.
• Hazards of ethers
• Preparation of ethers. WIlliamson synthesis
• Reactions of ethers. Cleavage by acids
• Analysis of alcohols
• Analysis of ethers

Review for Test 2 - Stereochemistry, Alkyl Halides, Alcohols and Ethers

Alkenes I. Structure and Preparation - Elimination

• Unsaturated hydrocarbons
• Structure of ethylene. The carbon-carbon double bond
• Propylene
• Hybridization and orbital size
• The butylenes
• Geometric isomerism
• Higher alkenes
• Nomenclature
  • IUPAC Nomenclature
  • Common Names
  • Cis or Trans
  • E,Z System
• Physical properties
• Industrial source
• Sayzeff's Rule
• Preparation
  • Dehydrohalogenation of alkyl halides
  • Dehydration of alcohols
  • Dehalogenation of vicinal dihalides
  • Reduction of alkynes
• Dehydrohalogenation of alkyl halides: 1,2 - elimination
• Kinetics of dehydrhalogenation. Duality of mechanism
• The E2 mechanism
• The E1 mechanism
• Dehydration of alcohols

Alkenes II. Reactions of the Carbon-Carbon Double Bond Electrophilic and Free-Radical Addition

• Reactions of alkenes
• Reactions at the carbon-carbon double bond. Addition
• Electrophilic addition: mechanism
• Electrophilic addition: rearrangements
• Electrophilic addition: orientation and reactivity
• Hydrogenation. Heat of hydrogenation
• Halogenation
• Heat of hydrogenation and stability of alkenes
• Addition of hydrogen halides. Markovnikov's rule.
• Regioselective reactions
• Addition of hydrogen bromide. Peroxide effect
• Addition of sulfuric acid
• Addition of water. Hydration
• Addition of alkanes. Alkylation
• Ozonolysis
• Analysis of alkenes

Sterochemistry II. Stereoselective and stereospecific Reactions

• Organic chemistry in three dimensions
• Stereochemistry of addition of halogens to alkenes. syn- and anti-addition
• Mechanism of addition of halogens to alkenes
• Stereochemistry of the E2 reaction. syn- and anti-elimination
• Stereospecific reactions
• Stereoselectivity vs. stereospecificity

Conjugation and Resonance - Dienes

• The carbon-carbon double bond as a substituent
• Free-radical halogenation of alkenes: substitution vs. addition
• Free-radical substitution in alkenes: orientation and reactivity
• Free-radical substitution in alkenes: allylic rearrangement
• Symmetry of the allyl radical
• The theory of resonance
• The allyl radical as a resonance hybrid
• Stability of the allyl radical
• Using the resonance theory
• Resonance stabilization of alkyl radicals. Hyperconjugation
• The allyl cation as a resonance hybrid
• Nucleophilic substitution in allylic substrates: S_N1.
• Reactivity. Allylic rearrangement
• Stabilization of carbocations: the resonance effect
• Nucleophilic substitution in allylic substrates: S_N2
• Nucleophilic substitution in vinylic substrates. Vinylic cations
• Dienes: structure and properties
• Stability of conjugated dienes
• Resonance in conjugated dienes
• Resonance in alkenes. Hyperconjugation
• Ease of formation of conjugation dienes: orientation of elimination
• Electrophilic addition to conjugated dienes. 1,4- Addition
• 1,2-vs. 1,4-Addition. Rate vs. equilibrium
• Free-radical polymerization of dienes. Rubber and rubber substitutes
• Isoprene and the isoprene rule
• Analysis of dienes

Alkynes

• Introduction
• Structure of acetylene. The carbon-carbon triple bond
• Nomenclature
  • IUPAC
  • Common
• Physical properties of alkynes
• Industrial source of acetylene
• Preparation of alkynes
  • Dehydrohalogenation of alkyl dihalides
  • Reaction of metal acetylides with primary alkyl halides
• Reactions of alkynes
  • Electrophilic addition to alkynes
  • Reduction to alkenes and alkanes
  • Addition of halogens
  • Addition of hydrogen halides
  • Hydration of alkynes. Tautomerism
  • Reactions of metal acetylides. Synthesis of alkynes
• Formation of carbon-carbon bonds. Role played organometallic compounds
• Analysis of alkynes

Cyclic Aliphatic Compounds

• Rings
• Nomenclature
• Ring shorthand
• Polycyclic
• Industrial sources
• Preparation
• Reactions
• Reactions of small ring compounds
• Stability of rings
• Factors affecting stability
• Stereoisomerism of cyclic compounds
• Crown ethers
• Epoxides

Aromaticity - Benzene

• Aliphatic and aromatic Compounds
• Structure of benzene
• Stability of benzene
• Resonance structure of benzene
• Reactions of benzene
  • nitration
  • sulfonation
  • halogenation
  • Friedel-Craft alkylation
  • oxidation
• Nomenclature of benzene derivatives
  • mono-substituted special compounds
  • di-substituted
• Polysubstituted
• Polynuclear hydrocarbons

Electrophilic Aromatic Substitution

• Introduction
• Reactions
• Effect of substituent groups
• Determination of orientation
• Determination of relative reactivity
• Classification of substituent groups
• Orientation of disubstituted benzenes
• Orientation and synthesis

Aromatic - Aliphatic Compounds. Arenes and Their Derivatives.

• The aromatic ring as a substituent
• Aromatic-aliphatic hydrocarbons: arenes
• Structure and nomenclature of arenes and their derivatives
• Physical properties
• Industrial source of alkylbenzenes
• Preparation of alkylbenzenes
• Friedel-Crafts alkylation mechanism
• Limitations of Friedel-Craft
• Rearrangement
• Reactions of alkylbenzenes
  • Hydrogenation
  • Oxidation of alkylbenzenes
  • Halogenation of alkylbenzenes: ring vs. side chain
  • Side-chain halogenation of alkylbenzenes
• Preparation of alkenylbenzenes.
• Reactions of alkenylbenzenes.

Spectroscopy and Structure

• Mass spec
• Infrared
• uv-visible
• Nuclear magnetic resonance

COURSE OBJECTIVES

Structure and Properties

• Define organic chemistry
• State covalence numbers.
• Define a covalent bond.
• Draw the three most common hybrid orbits.
• Predict solubilities.
• Define isomers.

Methane

• Classify the hydrocarbons into aliphatic or aromatic
• Draw the structure of methane
• State the common sources of obtaining methane.
• Determine the products of an oxidation reaction.
• Determine the products of a halogenation reaction and the mechanism.
• Define an inhibitor.
• Define heat of combustion, heat of reaction, and energy of activation.
• Assign a molecular formula given percent composition.

Alkanes

• Explain conformations around a single carbon bond.
• List the alkanes series and the respective formulas.
• Given a name, draw the structure of an alkane.
• Gives a structure, write the name of the alkane.
• Draw the isomers of alkanes.
• State the physical properties of alkanes.
• Draw the various preparations of alkanes.
• Write a halogenation reaction.
• Write a combustion reaction.

Stereochemistry

• Define stereochemistry and stereoisomer.
• Draw the three types of structures.
• Define optical activity.
• Define dextro and levorotary.
• Define specific rotation.
• Define enantiomers and draw them.
• Define chiral centers and draw.
• Define diastereomers.
• Define and draw meso structures.

Alkyl Halides

• Differentiate between homolytic and heterolytic.
• Define relative rates of competing reactions.
• Given a structure or name, draw the other.
• Prepare alkyl halides from alcohols.
• Prepare alkyl halides from halogenation of alkanes.
• Prepare alkyl halides through the addition of HX.
• Prepare alkyl halides through addition of halogens to alkenes and alkynes.
• Prepare alkyl halides by halide exchange.
• State the reactions of alkyl halides by nucleophilic substitution, dehydrohalogenation, in preparation of Grignard reagents and reduction.
• Define the kinetics and mechanisms of S₁N and S₂N.
• Describe carbocations.

Alcohols

• Write the structure of an alcohol given its common or IUPAC name.
• Given the structure of an alcohol, write the common or IUPAC name.
• State three industrial sources of alcohols.
• Write the hydrolysis of alkyl halides to produce alcohols.
• Write the reaction of alcohol with HX.
• Write the reaction of alcohol with PX₃.
• Write the dehydration of an alcohol.
• Write the reaction of alcohols with active metals.
• Write the esterification reaction.
• Write the oxidation products of primary, secondary, and tertiary alcohols.

Ethers

• Given the structure of an ether, write the IUPAC or common name.
• Given the IUPAC or common name of an ether, draw the structure.
• Show the preparation of a symmetrical ether.
• Show the preparation of an unsymmetrical ether.
• State the hazards of ethers.
• Show the reaction of ethers with HX.

Structure and Preparations of Alkenes

• Given the common or IUPAC name of an alkene, draw the structure.
• Given the structure of an alkene, write the common or IUPAC name.
• Draw the cis-trans or E,Z configurations of isomers.
• Show the industrial source of alkenes.
• Show a general elimination reaction, and show the two types: E1 and E2.
• Prepare an alkene through dehydrohalogenation of an alkyl halide.
• Prepare an alkene by the dehydration of alcohols.
• Prepare an alkene by dehalogenation of vicinal dihalides.
• Prepare an alkene by reduction of alkynes.

Reactions of Alkenes

• Show the reaction of alkenes by addition of hydrogen.
• Show the reaction of alkenes by addition of halogens
• Show the reaction of alkenes by addition of HX.
• Demonstrate Markonikov's Rule.
• Show the reaction of alkenes by addition of sulfuric acid.
• Show the reaction of alkenes by addition of water.
• Show the reaction of alkenes through alkylation.
• Show the reaction of alkenes by ozonolysis.

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