Organic Chemistry Study Guide And Solutions Manual
Егор Ульянов
My laboratory research interests are in mechanism-based drug design, organic reaction mechanisms in aqueous solution, enzyme mechanisms, and peptide chemistry. My last projects included the design, synthesis and evaluation of a family of aziridine-based inhibitors of the HIV protease, carboxy-terminal peptide degradation, and site-specific peptide cleavage reactions. Because of my activities in administration and teaching, I do not have a regular research group. However, I am available to serve on committees and to co-direct projects in other laboratories that are within my areas of expertise.
I am also studying (in collaboration with George Bodner in the Department of Chemistry) teaching and learning in organic chemistry. A current project involves comparison teaching of sophomore organic chemistry using cooperative learning and standard lecture approaches.
My current active interests are in university administration, teaching, and the developing of instructional materials. I am the author of Organic Chemistry, 5th Edition, published by Roberts and Company, and am a co-author of both Study Guide and Instructor Supplement to accompany that text. I have, in collaboration with George Bodner in the Division of Chemical Education, been developing a group-study approach to teaching organic chemistry, which has been implemented in the last several years in my organic chemistry course at Purdue (which has between 200-300 students). I am currently interested in working on a revision of the chemistry curriculum for pre-pharmacy, pre-medical, pre-biology, and pre-veterinary students.
Students who are going to be taking an ACS Examinations Institute exam have study materials available in some areas. The Institute is always working to expand this array of study materials. Right now, there are three printed study guides. We also have a variety of practice tests for students.
This guide includes 201 pages of information and over 600 problems separated into first-term and second-term general chemistry material. Each section contains 8 chapters of material that also aligns to most general chemistry textbooks for a seamless addition to study materials for students. Each chapter is designed with an introductory section of the material including common representations and where to find this material in a textbook. The second section provides worked examples of typical, multiple choice questions including how the correct answer is determined as well as how the incorrect answers were determined. Also included for each study problem is a listing of the corresponding practice questions that use that concept. The final section is a series of practice problems to test the concepts collectively. The key is provided on a separate page for all study and practice problems.
This guide is the newest update to our suite of study materials. A second edition was released in early 2020 with over 240 pages and over 600 unique problems. The guide is organized similarly to the general chemistry guide with a clear separation of first-term and second-term material. Each chapter is organized with study and practice questions where the study questions take you through the problem solving process of key problems explaining the correct process and also explaining the incorrect processes leading to incorrect answers. These study questions are then linked to practice questions where you can work through multiple choice questions and check your answers. Additionally, there are two culminating chapters linking all previous material: Multistep Synthesis and Applications of Organic Chemistry.
Aim of the course is to acquire knowledge and understanding, concepts and learning skills within the following domains:
1) Students should learn and understand the basic language of organic chemistry;
2) students should learn and understand the basic principles which connect the structure of organic compounds with their physic-chemical properties;
3) students should learn and understand the key concepts of the basic organic chemistry course in view of further in-depth study in the subsequent organic chemistry course.
At the end of the course, students having followed all the theory and exercise lessons are expected to be able to applying knowledge and understanding of the above mentioned subject areas through the correct execution of problems and exercises about:
1) recognizing, writing and naming the main organic molecule classes;
2) viewing simple organic molecules in three dimensions with an emphasis to their stereochemical properties;
3) recognizing and analyzing the relationship between structure and properties (reactivity) of basic organic molecules including alkanes, cycloalkanes, halogeno-alkanes, alkenes, alkynes, alcohols, polyols, ethers, epoxides, thiols;
4) proposing viable solutions as how to retro-synthesize, synthesize, transform, and interconvert the above mentioned organic compounds.
Further aim of the course involves the acquisition of learning skills and communication skills by employing appropriate language to both specialized and non-specialized audience, in line with the above mentioned objectives.
Origin and development of organic chemistry as a science. Functional groups of the main organic compounds. The carbon atom as a focal element in organic chemistry. Oxidation number assignment to a given atom within an organic molecule with a special emphasis on the carbon atom. Relationship between the structure of an organic compound and its physical and chemical behaviour. Hybridation (in aprticulr of the carbon atom within organic molecules), molecular geometry, electronegativity, polarity of organic compounds. Resonance in organic compounds. Configurational and conformational isomerism. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometric isomerism. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Radical and ionic reactions. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry, acid-base reactions. Oxidative-reductive reactions. Monomolecular and bimolecular nucleophilic substitutions at saturated carbons. Monomolecular and bimolecular beta-elimination reactions. Main solvents and their use in organic chemistry. Organometallic reagents, Grignard reagents: generality and use. Electrophilic addition reactions to alkenes and alkynes. Regioselective, stereospecific, and stereoselective organic reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, polyols, thiols, ethers, epoxides.
According to the above mentioned objectives and contents, the course is carried out through frontal oral lessons and includes exercises at the blackboard dealing with the design, synthesis, and transformation of simple organic molecules which could be connected with the pharmaceutical and biological domains. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course.
Classify the reactions of organic compounds, and characterize the structural aspects that confer and influence their reactivity and their physicochemical properties.
Understand the chemical reactions and mechanically justify the facts that have occurred.
Apply the knowledge of the reactivity of the different functional groups in order to obtain new compounds, that is, to project the knowledge acquired in organic synthesis, namely in the synthesis of potential drugs.
Acquire the concept of molecule geometry in the space associated with the study of stereochemistry.
Stimulate and develop the capacities for reflection and criticism, by carrying out review and application exercises of the acquired knowledge.
Develop scientific skills and attitudes, namely deductive reasoning, rigor, teamwork and observation.
Plan laboratory experiments, organize and interpret experimental data.
Apply laboratory safety rules and good practices in the use of material and equipment.
Develop the capacity for experimental, critical and self-assessment of the experiences made. Prepare accurate and reproducible reports.
It is intended that students acquire a clear vision of the potential and application of organic chemistry, as well as the reactivity and physicochemical properties of different groups of organic compounds.
With the knowledge acquired on chemical reactivity of organic compounds and stereochemistry, it is intended that students are able to acquire skills that will be essential for understanding the syllabus content of other more professionalizing MICF sylabus related to the pharmaceutical act, namely in the field of Pharmaceutical Chemistry, Biochemistry, Phytochemistry / Pharmacognosy and Pharmaceutical Technology.
Learn techniques for obtaining, isolation, purificationand control of the purity of samples of different origin, which are commonly used in the control of quality of medicines and synthesis of drugs.
It is alsoencouraged the development of the skills of reflection and critique,teamwork andlaboratory experiments planning, organization and interpretation ofexperimental data.
Study of organic compounds: alkanes, cyclic alkanes, haloalkanes, alkenes, alkynes, alkyl halides and aromatic compounds: Structures, nomenclature, physical-chemical properties, synthesis and reactivity, mechanisms. Conformational analysis. Stereochemistry: chiral compounds, optical activity, separation of enantiomers; stereochemistry in chemical reactions.
Execution of laboratory tasks aimed at the basic operations for the separation, purification and control of purity of organic compounds, namely:
- Analysis of a sulfamide mixture by analytical thin layer chromatography (CCF);
- Purification of a sulfamide mixture by preparative thin layer chromatography;
- Purification of a solid sample by crystallization and determination of the melting point of the crystals obtained;
- Isolation of Single Acid by continuous solid / liquid extraction;
- Nicotinamide extraction by continuous liquid / liquid extraction;
- Extraction of picric acid by continuous liquid / liquid extraction;
- Purification by preparative column chromatography (Dye separation).