Unit Summary

ORGANIC CHEMISTRY-2323 

Dr. Amorde

Unit Summary

Review

Fundamentals: The Basics

1. Atomic structural theory, Lewis structures, Formal charges, constitutional isomers, basic resonance theory

2. Atomic, molecular, and hybrid orbitals, covalent bonding, shapes of molecules

3. Polarity of molecules and bonds

4. Physical properties and intermolecular forces

5. Functional groups and families of organic compounds

6. Acid and base properties, equilibria, and relative acid/base strengths, structural features affecting acidity(e.g., inductive effects, resonance, hybridization, etc.), selection of appropriate conjugate base for H removal

7. Evaluate nucleophilic (basic) strength

8. Potential energy diagrams of reactions, activation energies of reactions

General Skills (We will work on these skills throughout the entire semester) Introduction to Mechanisms and Synthesis:

1. Introduction to mechanisms

2. Curved arrow notation

3. Basic retrosynthetic analysis

4. Synthesis of alkanes, alkenes, alkynes, and aromatic compounds

5. Hammond Postulate

Unit 1

Organic Nomenclature

1. IUPAC Nomenclature of alkanes, cycloalkanes, bicycloalkanes, alkenes, cycloalkenes, alkynes, alkyl halides, and aromatic compounds

2. Hydrocarbons (Alkanes, cycloalkanes)

3. Structure and physical properties

4. Homolytic bond dissociation Energies

5. Ring strain and conformations of cycloalkanes

6. Conformational analysis of ethane and higher alkanes

7. Cyclohexane- chair, boat, axial/equatorial positions, “flipping” between conformations

8. IR spectroscopy

9. Functional Groups

Unit 2

Hydrocarbons (Alkanes, cycloalkanes, and alkyl halides) Stereochemistry (Time permitting will be in unit 1)

1. Chirality

2. Optical activity, specific rotation, optical purity, enantiomeric excess

3. Enantiomers, diastereomers, meso compounds

4. R/S Nomenclature system for chiral molecules

5. Stereoisomerism of cyclic compounds

6. Stereochemistry in reactions

7. Resolution of a racemic mixture

Reactions and Their Mechanisms

1. Free radical reactions, halogenation of alkanes, radical addition to alkenes

2. Halogens and selectivity

3. Reduction of alkyl halides

Organic Acids and Bases

1. Acid and base properties, equilibria, and relative acid/base strengths, structural features affecting acidity(e.g., inductive effects, resonance, hybridization, etc.), selection of appropriate conjugate base for H removal

Unit 3

Hydrocarbons (Alkanes, cycloalkanes, alkyl halides, and alkenes)

1. IUPAC Nomenclature of alkenes, cycloalkenes, alkyl halides

2. E/Z Nomenclature system for alkenes

Reactions and Their Mechanisms

3. Nucleophilic substitution reactions (SN2 and SN1)

4. Elimination reactions (E2 and E1)

5. Dehydrohalogenation of alkyl halides, Zaitsev rules

6. Rearrangements of carbocation intermediates

7. Organometallics, Gillman reaction

Unit 4

Hydrocarbons (Alkanes, cycloalkanes, alkenes, alkynes, and dienes)

1. Stereospecific reactions

2. Conjugated dienes; their stabilities

3. Stability of allylic radicals and cations

Reactions and Their Mechanisms

1. Formation of halohydrins

2. Oxidations of alkenes and alkynes, syn-hydroxylation, oxidative cleavage, ozonolysis

3. Markovnikov’s rule and ant-Markovnikov’s reactions (Peroxide effect); Regioselectivity

4. Allylic substitution

5. 1, 2 and 1, 4 addition reactions; The Diels-Alder Reactions

6. Hydrogenation of alkenes

7. Addition of hydrogen halides, sulfuric acid, water, and halogens to alkenes

8. Grubb’s reaction

Unit 5

Hydrocarbons (Alkanes, cycloalkanes, alkenes, alkynes, dienes, and aromatics)

1. IUPAC Nomenclature of alkynes

2. Relative stabilities of alkynes

Reactions and Their Mechanisms

1. Alkylation of terminal alkynes

2. Addition of hydrogen halides, sulfuric acid, water, and halogens to alkynes

3. Debromination of vicinal dibromides

4. Hydrogenation of alkynes

5. Resonance theory

6. Aromaticity of benzene and other aromatic compounds

7. Huckel’s Rule

8. Antiaromatic, and Nonaromatic compounds

9. Electrophilic aromatic substitution reactions, halogenation, nitration, sulfonation, Friedel-
   Crafts alkylation, Friedel-Crafts acylation, effects of substituents on reactivity and orientation

10. Sonogashira and Heck couplings

11. Reactions of alkyl side chains on aromatic rings, benzylic halogenation, addition to alkenyl benzenes, oxidation of alkyl side chains

After the completion of this course, students will be able to:

1. Understand the structure and bonding of organic molecules

2. Understand the nomenclature of aliphatic and aromatic compounds

3. Understand conformational structures of alkanes

4. Recognize and assign stereochemical designations of organic compounds

5. Predict products from reactions of alkenes, alkynes, alkyl halides, dienes, and aromatic
   compounds based on a mechanistic understanding of these reactions and apply these reactions in multi-step syntheses

Assessment: The expected learning outcomes will be assessed through the use of homework, assignments and/or quizzes, regular exams and the final exam.