Organic Chemistry II

The course aims to provide an understanding of radical reactions, the relationship between the structure and chemical behavior of specific classes of organic compounds, and an introduction to the basic principles of spectroscopic techniques used to determine the structure of organic compounds.

In this course, students will acquire the knowledge and skills necessary to understand:

• The reactions that occur through free radical intermediates, including their structure, reactivity, and role in the chemical industry and human health.
• The structure and properties of alcohols and phenols, including methods of preparation, ways to protect the hydroxyl group during various transformations, and the reactions of substitution, elimination, and oxidation.
• The structure and properties of ethers and crown ethers, along with their preparation methods and associated reactions.

The text outlines various topics in organic chemistry, including:

• The preparation reactions of epoxides, the enantioselectivity of epoxidation, and the ring-opening reactions of epoxides.
• The structure and properties of thiols and sulfides.
• The nomenclature of aromatic compounds, their structures, stability, and aromaticity according to Hückel’s rule (4n + 2).
• The reactions of aromatic electrophilic substitution and nucleophilic aromatic substitution.
• Carbonyl chemistry, including nucleophilic addition reactions to the carbonyl bond, the role of oxygen and nitrogen nucleophiles, the formation of acetals, imines, and enamines, and the synthesis strategies and spectroscopic analysis of aldehydes and ketones.
• Synthetic strategies, selection of appropriate reagents, functional group transformations, carbon chain extension, and retrosynthetic analysis.
• The interaction of matter with electromagnetic radiation.
• Visible and ultraviolet spectroscopy (theory and applications).
• Spectrometry, including the principles of the method, the decomposition processes of various classes of organic compounds, along with examples and applications.
• Nuclear magnetic resonance spectroscopy (NMR), focusing on chemical equivalence, scaling, chemical shifts, spin-spin coupling, integration, decoupling techniques, and DEPT in obtaining ¹³C-NMR spectra.
• The combined use of spectroscopic techniques in the identification of organic compounds.
• Conjugated π systems and pericyclic reactions, including Diels-Alder reactions, electrocyclic reactions, and sigmatropic rearrangements.

Skills Development

• Identifying the weakest C-H bond in a compound
• Designing radical coordination structures
• Drawing the mechanism of radical halogenation
• Predicting the selectivity and stereochemical effects of radical bromination
• Predicting the products of radical reactions
• Designing steps to change the identity or position of a functional group or to modify the carbon skeleton
• Planning the steps for retrosynthetic analysis
• Comparing the acidity of alcohols
• Identifying oxidation and reduction reactions and predicting their products
• Preparing alcohols and selecting appropriate reagents
• Preparing ethers and epoxides
• Designing mechanisms and predicting products for epoxide reactions
• Selecting the appropriate Grignard reaction
• Nomenclature of benzene derivatives
• Determining the aromaticity of a structure
• Assessing the directing effects of substituents in electrophilic aromatic substitution
• Preparing aldehydes and ketones, selecting reagents, and determining nucleophilic addition products to carbonyls
• Designing compounds, transforming functional groups, and introducing two adjacent functional groups
• Analyzing IR spectra
• Distinguishing between two compounds using IR spectroscopy
• Analyzing mass spectra and understanding characteristic fragmentation patterns of organic compound classes
• Analyzing 1H-NMR and 13C-NMR spectra, determining the expected number of signals, identifying proton and carbon atom characteristics, predicting signal multiplicity, and differentiating compounds.
• Determining the degree of unsaturationon
• Determination of Molecular Structure Using Combined Spectroscopic Techniques:**
• Mechanism design and product prediction for electrophilic addition to conjugated diene compounds.
• Predicting the product of a Diels-Alder reaction.
• Predicting the product of an electrocyclic reaction.
• Using Woodward-Fieser rules to estimate λ max (maximum wavelength).

Upon completing the course, students will have developed the following key skills:

1. The ability to search for, analyze, and synthesize data and information using relevant technologies.
2. A strong respect for the natural environment.
3. The practice of critical thinking and self-reflection.
4. The promotion of creative and inductive thinking.