ORGANIC CHEMISTRY I
CHEM 2323/CHEM 2123
Lecture –
Lab -
Monday and Wednesday - TSC - Room 106 (4:00 PM)
Thursday - TSC - Room 106 (1:00 PM)
Thursday - TSC - Room 111 (2:00 PM)
Richard Wheet – Associate Professor Chemistry – 867- 4859 – richard.wheet@tstc.edu
Office Hours – Monday and Wednesday at 3:00 – 4:00 PM or by appointment
Website for Organic Chemistry – http://chemtech.org
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.
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:
o Hybrid orbitals: sp
o Hybrid orbitals: sp2
o 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
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
o from alcohols
o halogenation of hydrocarbons
o addition of hydrogen halide
o addition of halogens to alkenes
o addition of halogens to alkynes
o halide exchange
Reactions. Nucleophilic aliphatic substitution
Reactions of Alkyl Halides
o nucleophilic substitution
o dehydrohalogenation
o 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 SN2 reaction: mechanism and kinetics
The SN2 reaction: stereochemistry, Inversion of configuration
The SN2 reaction: reactivity. Steric hindrance
The SN1 reaction: mechanism and kinetics. Rate-determining step
Carbocations and the Structure of carbocations
The SN1 reactions: stereochemistry
Relative stabilities of carbocations
Stabilization of carbocations. Accommodation of charge.
Polar effects.
The SN1 reaction: reactivity. Ease of formation of carbocations
Rearrangement of carbocations
SN2 vs. SN1
Analysis of alkyl halides
Alcohols
Introduction
Structure of alcohols
Classification of alcohols
Nomenclature of alcohols
o common
o iupac
Physical properties of alcohols
Industrial source
o hydration of alkenes
o oxo process
o Fermentation of carbohydrates
Fuel from carbohydrates. Carbon dioxide balance
Ethanol
Preparation of alcohol
o hydrolysis of alkyl halides
o grignard synthesis
Reactions of alcohol
o reaction with hydrogen halide
o reaction with phosphorus trihalides
o dehydration
o reaction as acids
o ester formation
o oxidation of primary alcohol
o oxidation of secondary alcohol
o 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
o common and 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 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
o IUPAC Nomenclature
o Common Names
o Cis or Trans
o E,Z System
Physical properties
Industrial source
Sayzeff's Rule
Preparation
o Dehydrohalogenation of alkyl halides
o Dehydration of alcohols
o Dehalogenation of vicinal dihalides
o 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: SN1.
Reactivity. Allylic rearrangement
Stabilization of carbocations: the resonance effect
Nucleophilic substitution in allylic substrates: SN2
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
o IUPAC
o Common
Physical properties of alkynes
Industrial source of acetylene
Preparation of alkynes
o Dehydrohalogenation of alkyl dihalides
o Reaction of metal acetylides with primary alkyl halides
Reactions of alkynes
o Electrophilic addition to alkynes
o Reduction to alkenes and alkanes
o Addition of halogens
o Addition of hydrogen halides
o Hydration of alkynes. Tautomerism
o 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
o nitration
o sulfonation
o halogenation
o Friedel-Craft alkylation
o oxidation
Nomenclature of benzene derivatives
o mono-substituted special compounds
o 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.
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
o Hydrogenation
o Oxidation of alkylbenzenes
o Halogenation of alkylbenzenes: ring vs. side chain
o Side-chain halogenation of alkylbenzenes
Preparation of alkenylbenzenes.
Spectroscopy and Structure
Mass spec
Infrared
uv-visible
Nuclear magnetic resonance
REQUIRED STUDENT MATERIALS & SUPPLIES
notebook
pens
safety glasses
stirring bars
bound laboratory notebook (numbered pages)
GRADING POLICY
The final grade will be based on the average all major tests and the average of the quizzes
(which count as one major test)
Grade:
A = 90 - 100
B = 80 - 89
C = 70 - 79
D = 60 - 69
F = 59 and below
There are no makeups for any missed tests or quizzes. A grade of zero will be recorded
for failure to take a test or a quiz on its scheduled time and day.
ATTENDANCE POLICY
Refer to current Chemical Technology attendance policy.
The student must be present for all tests, quizzes, and assignments. Failure to attend will
result in a grade of zero for that particular test, quiz or assignment.