Student achievement objectives are listed after each section below: - General Principles
Definition of organic chemistry. Atomic structure. Atomic orbitals and electron configuration. Chemical bonds: ionic, covalent, and coordinate covalent. Molecular and structural formulas. Use of atomic orbitals in covalent bond formation. Sigma and pi bonds. The charges on common elements. The covalence of common elements. Formal charges. Carbocations, free radicals, and carbanions. Functional groups.
Section I - At the end of this section, the student should be able to:
1. Understand why there are so many organic compounds.
2. List some common elements, besides carbon, found in many organic compounds.
3. Describe the type of orbitals found in each of the first four main energy levels.
4. Write the electron configuration for any of the first twenty elements, when given the atomic number of the element.
5. State the octet rule and understand its significance.
6. Describe the formation of ionic, covalent, and coordinate covalent bonds.
7. List common elements which enter into ionic bond formation, and their charges.
8. List common elements, which enter into covalent bond formation, and their usual covalence.
9. Describe the characteristics of ionic and covalent compounds.
10. Write Lewis structures for ionic substances and for covalent molecules, including organic molecules with multiple bonds.
11. Differentiate between molecular and structural formulas.
12. Describe covalent bond formation using atomic orbitals of atoms.
13. Distinguish between a sigma and pi molecular orbital.
14. Calculate formal charges on atoms in Lewis structures.
15. Describe the nature of three unstable reaction intermediates found in many organic reactions.
16. Recognize the structures of common organic compounds such as: alkenes, alkynes, alcohols, phenols, ethers, aldehydes, ketones, amines, amides, and carboxylic acids, based on their functional groups.
- Acids and Bases
The Arrhenius concept of acids and bases. The Bronsted theory of acids and bases. Conjugate acid-base pairs. Dissociation and ionization constants. Electronegativity. Effect of electronegativity on acidity and basicity. Acidity and the separation of mixtures. Lewis theory of acids and bases. Lewis acids as catalysts in organic reactions.
Section II - At the end of this section, the student should be able to:
1. Give the Arrhenius definition of acids and bases.
2. Write an equation showing the reaction of an Arrehenius
acid and base.
3. Give the Bronsted definition of acids and bases.
4. Explain how a non-Arrhenius base can qualify as a Bronsted base.
5. Explain how water can act as either an acid or a base.
6. Define what is meant by a conjugate acid-base pair.
7. Identify the conjugate acid-base pair in a chemical equation.
8. Explain how the relative strengths of acids and bases can be determined from ionization and dissociation constants.
9. Define the meaning of electronegativity and explain how it varies in the periodic table.
10. Explain how electronegativity can affect the acidity or basicity of compounds.
11. Compare the acidity of strong acids, carboxylic acids, alcohols, amines, and hydrocarbons.
12. Write chemical equations showing the reaction of a Grignard reagent with strong acids, carboxylic acids, alcohols, and amines.
13. Define the meaning of the terms nitride ion, allkoxide ion, and carboxylate ion.
14. Explain why sodium bicarbonate will react with carboxylic acids, but not with alcohols, amines, and hydrocarbons.
15. Describe the process of separating a mixture of a water insoluble alcohol and a water insoluble carboxylic acid.
16. Explain how the ammonium salt of an amine can be converted to its free amine.
17. Give the Lewis definition of acids and bases.
18. Provide examples of Lewis acids and bases.
19. Define the terms electrophilic and nucleophilic as they relate to Lewis acids and bases.
20. Explain how Lewis acids are used as catalysts in the formation of carbocations.
- Isomers and Spectroscopy
The tetrahedral bond angle in methane. The equivalency of the bonds in methane. Conformations of ethane: eclipsed and staggered. Conformers. Isomers. Functional isomerism. Structural isomerism. Identification of isomers by chemical methods. Identification of isomers using spectroscopy. Electromagnetic radiation. Principles of spectroscopic analysis. Ultraviolet-visible spectroscopy. Infrared spectroscopy. Nuclear magnetic resonance spectroscopy.
Section III - At the end of this section, the student should be able to:
1. Describe the tetrahedral structure of the methane molecule.
2. Explain how all the carbon-hydrogen bonds in methane are equivalent.
3. Differentiate between the eclipsed and staggered conformations of ethane.
4. Define functional isomerism and give examples.
5. Define structural isomerism using the isomeric pentanes as an example.
6. Give examples of how chemical methods can be used to differentiate among different isomeric structures.
7. Explain the feature that is common among the instrumentation used to determine the structure of molecules.
8. Provide examples of radiations that are part of the electromagnetic spectrum.
9. Explain how the frequency and wavelength of electromagnetic radiation are related.
10. Write equations showing how the energy of a photon associated with a certain type of radiation is related to its frequency and wavelength.
11. Draw a schematic diagram of a spectrophotometer.
12. Discuss what is occurring in compounds that absorb ultraviolet and visible light.
13. Describe the structural feature that must be present for a compound to absorb ultraviolet and visible light.
14. Explain what the absorption of infrared photons does to an organic molecule.
15. Discuss how the absorption of infrared photons helps to identify the type of functional group and molecular structure present.
16. Describe what occurs when hydrogen nuclei in a magnetic field absorb photons of radio-frequency radiation.
17. Explain the significance of a proton NMR spectrum in terms of: (a) the number of signals, (b) the chemical shift of each signal, (c) the area under each peak, and (d) the number of peaks into which each signal is split.
UNIT EXAM I
- Alkanes and Cycloalkanes
General characteristics of alkanes. Bond orbitals of methane. sp3 hybridization. Nomenclature: systematic-IUPAC and naming alkanes as derivatives of methane. Alkyl groups. Applying the rules of nomenclature to isomers of the first six alkanes. Methods of preparing alkanes. Cycloalkanes. Conformations of cyclohexane. Equatorial and axial hydrogens. Conformation of methyl cyclohexane. Reactions of alkanes.
Section IV - At the end of this section, the student should be able to:
1. Identify the molecular formula of an alkane.
2. Explain how the hybridization of carbon's atomic orbitals results in the formation of four equivalent sp3 hybrid atomic orbitals.
3. Draw the molecular orbital picture of methane.
4. Write the names of the first ten unbranched alkanes.
5. Distinguish among primary, secondary, and tertiary carbon atoms.
6. Name the isomeric alkyl groups that contain up to four carbon atoms.
7. Name an alkane using either the systematic IUPAC system or the derivative of methane system.
8. Write the structural formula of an alkane from its name and vice versa.
9. Know which reactions are used in the preparation of alkanes.
10. Recognize the difference in the molecular formulas of cycloalkanes and alkanes.
11. Draw the two conformations of cyclohexane.
12. Explain why the chair conformation of cyclohexane is more stable than the boat conformation.
13. Differentiate between the equatorial and axial hydrogen atoms of cyclohexane.
14. Understand the preferred conformation of the methyl group in methyl cyclohexane.
15. Write the mechanism for the chlorination of methane.
16. Know which reactions are typical of the alkanes.
- Small Rings, Alkenes, and Alkynes
Reactions of small ring compounds. General characteristics of alkenes. Bond orbitals of ethylene. sp2 hybridization. Nomenclature of alkenes. Cis-trans isomerism. Reactions of alkenes. Markovnikov's rule. Peroxide effect. Preparation of alkenes. Elimination reactions. General characteristics of alkynes. Bond orbitals of acetylene. sp hybridization. Nomenclature of alkynes. Reactions of alkynes. Addition to the triple bond. Reactions of the terminal
= C-H bond. Preparation of alkynes.
Section V - At the end of this section, the student should be able to:
1. Explain the reactivity of small ring compounds.
2. Write chemical equations illustrating three typical small ring opening reactions.
3. Identify the molecular formula of an alkene.
4. Explain how hybridization of carbon's atomic orbitals results in the formation of three equivalent sp2 hybrid atomic orbitals as found in double bonds.
5. Draw the molecular orbital picture of ethylene.
6. Write the correct IUPAC name for an alkene on the basis of a given structural formula and vice versa.
7. Differentiate between cis-trans isomers.
8. Write chemical equations showing five typical alkene addition reactions.
9. Explain and give an example of Markovnikov's rule and the peroxide effect.
10. Write chemical equations illustrating two methods by which alkenes can be prepared.
11. Describe the E2 and E1 mechanism of dehydrohalogenation of alkyl halides, clearly identifying the role of the base.
12. Identify the molecular formula of an alkyne.
13. Explain how hybridization of carbon's atomic orbitals results in the formation of two equivalent sp hybrid atomic orbitals as found in triple bonds.
14. Draw the molecular orbital picture of acetylene.
15. Write the correct IUPAC name for an alkyne on the basis of a given structural formula and vice versa.
16. Write chemical equations showing four typical alkyne addition reactions.
17. Account for the reactivity of sodium amide with a 1-alkyne but not with a 2-alkyne.
18. Show how an alkyne can be prepared from an alkene.
UNIT EXAM II
- Aromatic hydrocarbons
The structure of benzene. Resonance. Rules for resonance. The molecular orbital picture of benzene. Nomenclature: (a) the systematic and common names of aromatic hydrocarbons, (b) ortho, meta, para system, (c) the numbering system. Reactions of benzene: (a) nitration, (b) sulfonation, (c) halogenation, (d) Friedel-Crafts alkylation. Orientation in aromatic substitution. Synthesis of aromatic compounds using the rules of orientation. Side chain halogenation. Other aromatic ring systems. Huckel's rule.
Section VI - At the end of this section, the student should be able to:
1. Explain why a six membered ring of carbon atoms containing alternating single and double bonds is not an accurate representation of the benzene molecule.
2. Define the term resonance and list the rules for resonance.
3. Draw the molecular orbital picture of benzene and indicate how it can be used to account for some of the structural characteristics of benzene.
4. Write a structural formula for an aromatic compound on the basis of its IUPAC name and vice versa.
5. Explain the meaning of the ortho, meta, para systems, for naming di-substituted benzene derivatives.
6. Provide an explanation as to why benzene does not easily undergo addition reactions.
7. Explain the meaning of electrophilic aromatic substitution.
8. Write chemical equations describing the electrophilic aromatic substitution reactions of benzene: nitration, sulfonation, halogenation, and Friedel-Crafts alkylation.
9. Draw the structure of the electrophile in each of the substitution reactions of benzene.
10. State the rule which characterizes certain groups as either ortho, para directors or meta directors.
11. Show by using the reactive intermediate resonance structures of benzene, why alkyl groups, -C1, -Br, and -OH will direct an entering group to the ortho and para positions. Do the same for the meta directing groups.
12. Write chemical equations showing the synthesis of disubstituted aromatic compounds.
13. Write structures for other aromatic ring systems besides benzene.
14. Predict whether a substance is aromatic based on its structure and Huckel's rule.
- Alcohols, Ethers, and Phenols
Classes of alcohols. Systematic and common names of alcohols. Reactions of alcohols. The Lucas test for alcohols. Preparation of alcohols. Nucleophilic substitution reactions: SN2 and SN1 reactions. Ethers. Systematic and common names of ethers. Preparation of ethers. Reactions of ethers. Phenols. Naming phenols. Reactions of phenols. Separation of phenols from alcohols and carboxylic acids. Preparation of phenols.
Section VII - At the end of this section, the student should be able to:
1. Differentiate on the basis of structure: primary, secondary, and tertiary alcohols.
2. Write a structural formula for an alcohol on the basis of its systematic or common name and vice versa.
3. Explain the reactivity of primary, secondary, and tertiary alcohols, toward sodium.
4. Explain how the Lucas test is used to distinguish among primary, secondary, and tertiary alcohols.
5. Explain what is meant by the phrase "bimolecular nucleophilic substitution."
6. Predict the effect of steric crowding on an SN2 reaction.
7. Explain what is meant by the phrase "unimolecular nucleophilic substitution."
8. Explain how carbocation stability affects the rate of an SN1 reaction.
9. Indicate how primary, secondary, or tertiary alkyl halides, undergo hydrolysis to form alcohols by either an SN2 or SN1 reaction.
10. Outline the steps involved in hydration and hydroboration of an alkene.
11. Write chemical equations showing the reaction of Grignard reagents with aldehydes and ketones to produce primary, secondary, and tertiary alcohols.
12. Write a structural formula for an ether on the basis of its systematic or common name and vice versa.
13. Describe the steps involved in the Williamson ether synthesis.
14. Name the organic compounds obtained as a result of cleavage of ethers by strong acids.
15. Account for the fact that phenols but not alcohols react with sodium hydroxide.
16. Explain how a phenol can be separated from a carboxylic acid and an alcohol.
17. Show how a diazonium salt can be converted to phenol.
- Aldehydes, Ketones, and Quinones
The carbon-oxygen double bond. Nomenclature of aldehydes and ketones. Preparation of aldehydes and ketones. Addition reactions of the carbonyl group: addition of hydrogen, water, alcohols, Grignard reagents, hydrogen cyanide, and amines. Enolization. The aldol condensation. Oxidation of aldehydes and ketones. The Tollen's test. The haloform reaction. Quinones.
Section VIII - At the end of this section, the student should be able to:
1. Write a structural formula for an aldehyde or ketone on the basis of its systematic or common name and vice versa.
2. Name some aldehydes and ketones found in nature.
3. Write chemical equations showing how aldehydes and ketones can be prepared from: oxidation of alcohols, hydrolysis of gem-dihalides, and by addition of water to alkynes.
4. Describe how the polar nature of the carbonyl group affects nucleophilic additions to aldehydes and ketones.
5. Show the addition of hydrogen to an aldehyde or a ketone and the product that is produced.
6. Write a chemical equation for the hydration of an aldehyde or a ketone.
7. Describe through the use of chemical equations, how an acetal is produced from the reaction of an aldehyde or a ketone with an alcohol.
8. Show through the use of chemical equations the reaction of a Grignard reagent with an aldehyde or ketone.
9. Write chemical equations describing the reaction of an aldehyde or a ketone with a primary amine and with hydrazine derivatives.
10. Describe by using a chemical equation, the formation of a cyanohydrin.
11. Write the mechanism showing the aldol condensation of an aldehyde.
12. Write a chemical equation for the oxidation of an aldehyde.
13. Describe a positive Tollen's test.
14. Draw the structure of an aldehyde or a ketone which will produce a positive haloform reaction.
15. Recognize quinone type structures in organic compounds.
16. Write a chemical equation describing the formation of a quinone by the oxidation of 1,4-dihydroxybenzene.
UNIT EXAM III
- Stereochemistry
Mirror images and chirality. Enantiomers. Chiral centers. Perspective and Fischer projections. Plane polarized light. The polarimeter. Optical activity. Plane of symmetry. Synthesis of chiral molecules. Absolute configurations. The R-S notational system of absolute configuration. Diastereomers. Meso compounds. Naming stereoisomeric alkenes by the E-Z system. Molecules with two or more chiral centers. Resolution of enantiomers.
Section IX - At the end of this section, the student should be able to:
1. Identify a chiral molecule by locating a chiral carbon atom.
2. Explain what is meant by the term enantiomer.
3. Explain what is meant by the term diastereomer.
4. Draw perspective representations of chiral molecules.
5. Draw Fischer projections of chiral molecules.
6. Describe how a plane of symmetry relates to whether or not
a molecule is chiral.
7. Explain optical activity as a property of chiral molecules.
8. Specify the absolute configuration of a molecule using the
R-S notational system.
9. Specify alkene stereochemistry using the E-Z notational system.
10. Explain why addition reactions to achiral alkenes give racemic mixtures of products.
11. Explain the meaning of the term meso isomer.
12. Give the number of stereoisomers possible for a molecule having more than one chiral center.
13. Describe how a racemic mixture may be resolved into individual enantiomers.
- Carboxylic Acids and Related Compounds.
Acidity of carboxylic acids. Systematic and common names of carboxylic acids. Preparation of carboxylic acids. Reactions of carboxylic acids and their derivatives. Formation of salts. Formation of acid halides. Reactions of acid halides. Formation of acid anhydrides. Reactions of acid anhydrides. Formation of esters. Reactions of esters. Preparation of soap. Formation of amides. Reactions of amides.
Section X - At the end of this section, the student should be able to:
1. Explain the acidic nature of carboxylic acids.
2. Write a structural formula for a carboxylic acid on the basis of its systematic or common name and vice versa.
3. Write chemical equations showing how carboxylic acids can be prepared from: oxidation of primary alcohols, hydrolysis of nitriles, and carbonation of Grignard reagents.
4. Describe how to prepare salts of carboxylic acids, and explain the process of liberating the free carboxylic acid from its salt.
5. Give two chemical equations which lead to the formation of acid halides.
6. Name the organic compound formed as a result of the reaction of an acid halide with an alcohol.
7. Show the reaction of an acid halide with benzene in the presence of a Lewis acid.
8. Write a chemical equation showing how an acid anhydride can be prepared from an acid halide and the sodium salt of a carboxylic acid.
9. Specify the product formed as a result of the reaction between salicyclic acid and acetic anhydride.
10. Show the products obtained as a result of an acid anhydride undergoing hydrolysis, alcoholysis, and ammonolysis.
11. Define the term esterification. Show the mechanism as to how this process takes place.
12. Write a chemical equation showing the reaction of an ester with sodium hydroxide. What is this reaction called.
13. Specify the reactants that are required in order to produce a fat.
14. Describe the substance that is produced as a result of saponification of a fat.
15. Explain how a tertiary alcohol is formed as a result of the reaction of an ester with two moles of a Grignard reagent.
16. Give two reactions in which an amide can be produced.
17. Show how amides can undergo dehydration to produce nitriles.
18. Explain the nature of the bond that joins long chains of amino acids to form proteins.
- Amines
Classes of amines. Systematic and common names of amines. Base strength of amines. Preparation of amines: alkylation of ammonia, the Hofmann reaction, reduction of nitriles, and reduction of nitrobenzene. Reactions of amines.
Section XI - At the end of this section, the student should be able to:
1. Differentiate on the basis of structure; primary, secondary, and tertiary amines.
2. Write a structural formula for an amine on the basis of its systematic or common name and vice versa.
3. Compare the base strength of alkyl amines to ammonia and aromatic amines.
4. Write a chemical equation for the reaction of an amine with an acid.
5. Write a chemical equation describing the preparation of an alkylamine by alkylation of ammonia.
6. Describe how to prepare an alkylamine by reduction of an amide.
7. Show how a primary amine can be prepared by reduction of a nitrile.
8. Write a chemical equation describing the preparation of an arylamine from an aromatic nitro compound.
9. Show how a quaternary ammonium salt can be prepared from a tertiary amine.
10. Use a chemical equation to describe the reaction of an amine with an alkyl halide.
11. Explain how primary amines and monosubstituted ammonias such as hydroxylamine, can be used in the identification of aldehydes and ketones.
UNIT EXAM IV
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