Organic Chemistry I

The course aims to equip students with the essential knowledge and skills to understand the fundamental principles of Organic Chemistry and apply them to problem-solving scenarios.

Specifically, throughout the course, students will gain expertise in the following areas:

• The structural theory of matter. Τhe role of electrons in bond formation and their influence on the molecular properties of organic compounds. Ηybridized atomic orbitals and the geometry of organic molecules.  Polarity, Intermolecular Forces and Solubility of Molecules. Molecular representations, functional groups, and the nomenclature rules of organic compounds. Three-dimensional bond-line structures, resonance structures, and formal charges. Delocalized and localized electron pairs.
• Bronsted-Lowry and Lewis Acids and Bases.
  • Understanding the quantitative and qualitative approaches to acidity
  • The position of equilibrium in acid-base organic reactions and choice of reagents
  • Leveling Effect. Solvating Effects.
• Alkanes and Cycloalkanes.
  • The relative stability of isomers
  • Newman projections and conformational analysis of alkanes
  • Conformations of cyclohexane
  • Cis-trans stereoisomerism in cycloalkanes
• Stereoisomerism
  • Concepts of symmetry and chirality
  • Determination of stereoisomers through imaging
  • Enantiomers and diastereomers
  • Fischer projections
• Chemical Activity and Mechanisms
  • Terms related to enthalpy, entropy, and free energy according to Gibbs in organic reactions
  • Equilibrium and kinetics of reactions
  • Energy diagrams, nucleophilic and electrophilic reagents
  • Electron movement patterns and carbocation rearrangements
• Substitution Reactions
  • Mechanisms of SN2 and SN1 reactions
  • Factors determining which mechanism prevails
• Alkenes
  • Stereoisomerism in alkenes and their relative stability
  • E2 and E1 elimination mechanisms
  • Factors that influence the choice between substitution and elimination mechanisms
  • Product prediction
• Addition Reactions of Alkenes
  • Rules governing the addition mechanism
  • Types of addition reactions: hydrogenation, hydration, oxyhydration-dehydration, hydroboration-oxidation, catalytic hydrogenation, halogenation, anti and syn dihydroxylation, and oxidative degradation
• Alkynes
  • Acidity of terminal alkynes
  • Preparations and reactions of alkynes, including reduction, hydrogenation, hydration, halogenation, ozonolysis, and alkylation
• Synthesis Strategies
  • Selecting reagents for the transformation of functional groups

Skill Development

• Identification of the Structural Formula
• Designing Lewis structures and calculating the formal charge of atoms
• Prediction of geometry, molecular dipole moments, and physical properties
• Identification and design of skeletal structures
• Drawing significant resonance structures and assigning formal charges
• Identifying localized and delocalized lone pairs
• Design of the proton transfer mechanism
• Utilization of pKa values to compare acidic and basic character and predict equilibrium position
• Prediction of equilibrium position without using pKa values by evaluating relative stability based on ARIO factors
• Selection of the appropriate reagent for a proton transfer reaction
• Identification of organic acids and Lewis bases
• Name organic compounds
• Designing structural isomers
• Creating Newman projections and evaluating the relative energy of various configurations
• Design of chair conformations for cyclohexane, including axial and equatorial positions, and identification of the most stable configuration for multi-substituted cyclohexane
• Identification of cis-trans stereoisomerism
• Finding and naming chiral centers. The R- and S- system.
• Calculation of the specific rotation and enantiomeric excess
• Determination of the stereoisomeric relationship between two compounds and identification of meso compounds
• Identification of nucleophilic and electrophilic centers
• Drawing curved arrows and sequences of electron flow patterns
• Predicting carbocation rearrangements
• Designing the complete mechanism of an SN2 process and predicting the product
• Designing the complete mechanism of an SN1 process and predicting the product
• Determining whether a reaction proceeds via an SN1 mechanism or an SN2 mechanism
• Identifying the reagents needed for a substitution reaction
• Defining the stereoisomerism of the C=C double bond
• Comparing the stability of isomeric alkenes
• Designing the mechanism of an elimination reaction
• Predicting the topochemical and stereochemical effects of E2 and E1 reactions
• Determining whether a reagent acts as a nucleophile or a base and predicting the expected mechanism
• Predicting the products of substitution and elimination reactions.
• Predicting the products of alkene addition reactions
• Predicting the equilibrium position for the deprotonation of a terminal alkyne
• Designing the mechanism of keto-enol tautomerization
• Predicting the products of alkyne reactions
• Developing synthesis strategies, selecting suitable reagents, and interconverting alkanes, alkenes, and alkynes

Upon completing the course, students will have developed the following skills: the ability to search, analyze, and synthesize data and information using necessary technologies; respect for the natural environment; and the promotion of free, creative, and inductive thinking.