Study Guide Solutions Manual For Organic Chemistry

[Latisha Gervase]

Mylaboratory 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.

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.

This unit serves the needs of students who wish to major in chemistry or biomolecular sciences, as well as those pursuing related disciplines in biological, medical, materials and health sciences. It will be valuable to anyone with an interest in how organic and inorganic compounds react with one another, and how chemists use this knowledge of molecular interactions to synthesise new compounds with desirable properties (eg, new pharmaceuticals, new catalysts, and new materials). The unit focuses on the principles, mechanisms and synthetic procedures of organic and inorganic compounds. Topics include: chemical reactivity; stereochemistry; introduction to the spectroscopic identification of compounds; reaction mechanisms; and synthetic methods. The study of these mechanisms and methods provides an understanding of chemical processes and reactivity applicable in designed and living systems. The practical component is aimed at developing laboratory skills and deductive reasoning; it comprises syntheses of various classes of compounds and identification of unknown compounds by chemical and spectroscopic means.

Hurdle Activities As explained in the assessment section, practials/experiments are the hurdle activities as they have interconnected learning outcomes and demonstrate the necessary techniques. A passing grade in the practical component (hurdle) is required to pass the unit. You are allowed one missed practical without a medical certificate but missing two or more practicals even with approvals means serious risk of failing the unit, in whick case you must consult with the unit convenor for options or you will fail the unit if left unaddressed. Further details are in the laboratory manual/notes (see the iLearn website).

Special Consideration The Special Consideration Policy aims to support students who have been impacted by short-term circumstances or events that are serious, unavoidable and significantly disruptive, and which may affect their performance in assessment. If you experience circumstances or events that affect your ability to complete the assessments in this unit on time, please inform the convenor and submit a Special Consideration request through ask.mq.edu.au.

These experiments have interconnected learning outcomes and demonstrate the necessary techniques. Some of the practical sessions will be done in the format of "dry-lab" (e.g. workshops) to develop independence in problem solving.

Circumstances such as routine demands of employment/financial need or extra-curricular activities, routine family problems, and difficulties adjusting to university life and stress associated with the demands of academic work, are not unforeseeable circumstances beyond your control and should not be used as an excuse to miss a class. Most of the class material will be available on the unit website, while there will be some provided in class. While recorded lectures are available in this unit, they must not be used in place of active class participation but rather serve as useful resources for reviewing the content.

SGTAs are critical for effective learning with demonstrations of how to solve problems in order to do well in tests/exams. There are no SGTAs in week 1. Regular attendance of a SGTA is key to keeping up with the unit content.

Practicals are compulsory and must be done on-campus. The detailed lab practical notes/ workshop schedule is provided through the unit's iLearn website. The class is divided into two groups (Group A and Group B) for attending the practicals/ workshops according to Group A Schedule and Group B Schedule (on iLearn). Participation in the practicals is compulsory, and no make-up labs will be available. Failure to attend more than once without a special consideration approval will result in being failed. There are no practicals in the 1st week. The students are to use the 1st week practical time to self study and prepare for general practical requirements such as performing risk assessments of experiments and safety review. Please see iLearn instructions for details.

Some of the practical sessions will be used as workshops, and your attendance and active participation in the workshop sessions is compulsory and marks will be awarded for your interactive contributions. The class is divided into two groups (Group A and Group B) for attending the workshops (as well as practicals, please see the next paragraph) according to Group A Schedule and Group B Schedule (on iLearn). Students are expected to attempt the questions prior to attending and bring in all relevant course notes and textbooks for the workshops. The workshop problems will be on the iLearn website closer to the dates. Workshops are long, guided problem-solving sessions where you will be asked to answer final exam style questions with more independence - some exam questions will be drawn straight from the workshop questions. The location will be announced via iLearn. Once you have chosen your group (A or B) and a practical session, you will attend the same session slot for the entire semester. You must regularly check the unit web page for course related information. The web page for this unit can be found at:

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