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Jordan University of Science and Technology Faculty of Science and Arts Department of Chemistry Second Semester 2007 Course Title Course Information Organic Chemistry Course Number Chem. 217 Prerequisites Chem. 103 Course Website Under-construction Instructor Dr. Khaled Shawakfeh Office Location N4L0 Office Phone Tel. # 7201000 Ext. 23646 Office Hours Mon & Wed at 11:15-1:15. E-mail [email protected] Teaching Assistant None Course Description This course deals primarily with the basic principles of organic chemistry in order to understand the structures and reactivity of organic molecules This course also deals mainly with the constitution and properties of the different classes of organic compounds, with considerable attention to stereochemistry, reaction mechanisms, synthetic organic chemistry and Surveys the chemistry of functionalized organic compounds emphasizing mechanisms and multi-step syntheses.. Emphasis will be on substitution and elimination reactions , the chemistry of hydrocarbons, alkyl halides, alcohols, carbonyl compounds, and amines. Text Book Title Organic Chemistry, A Short Course Author(s) Hart/Craine/Hart/Hadad Publisher Houghton Mifflin Year 2007 Edition 12th Ed. www.brookscole.com Organic Chemistry, John McMurry Book Website References Assessment Policy Assessment Type First Exam Expected Due Date Mon March 19, 2007. Second Exam Sat Final Exam May 26- June 4, 2007 Assignments April 28, 2007. Weight 30% 30% 40% Course Objectives 1. Name simple organic compounds and draw their structures. Weights 15% 2. Compare the physical and chemical properties for different organic compounds. 3. Write reaction equations, Mechanisms and possible intermediates, Transition states with relative energy. 4. Differentiate the orientation of substitution in the electrophonic aromatic substitution reactions of mono substituted benzene. 5. Synthesis of simple organic compounds from simple organic materials. 10% 6. Study the water derivatives (Alcohol, Ether, Thiols and Sulfides) 10% 7. Prepare derivatives like esters, anhydrides, acid chlorides and amides from the corresponding carboxylic acids. 8. Understand the relationship between structure and acidity, basicity and reactivity of organic compounds. 9. Learn some applications of organic molecules and reactions in medicine biochemistry, pharmacology, and some industrial applications 10. Learn simple multi step synthesis with their stereochemistry 10% 5% 20% 5% 10% 10% 5% Teaching & Learning Methods Class periods will be a mixture of theory, analysis, demonstration, and discussion. I believe in the active-learner approach. You are required to read organic chemistry (I) before registering for this class. Learning Outcomes: Upon successful completion of this course, students will be able to Reference(s) Related Objective(s) 1 Chapter 1-10 2 Chapter 2-10 3 Chapter. 3, 4 4 Chapter 5 5 Chapter 6 6 Chapter 7-10 7 Chapter 9, 10 8 Chapter 7, 9, 10 9 Chapter 5-10 10 Chapter 5, 7, 9, 10 Useful Resources Organic Chemistry, John McMurry Course Content Week Topics 1 The nature of chemical bond, hybridization, acids & bases Alkanes , structure & isomers, conformations, cycloalkanes, cis- ttrans isomers, conformations, axial & equatorial bonds in cyclohexane Reactions of alkanes, alkenes, structure, naming, cis- trans isomers Chapter 2 Kinds of organic reactions, reaction mechanisms ( free radical & polar ) Chapter 3 2 3 4 5 6 7 8 9 10 Reactions of alkenes, addition of HCl, addition of water, addition of halogens, oxidation,Hydroboration- oxidation, reduction, polymerization, addition reactions in dienes Alkynes, structure, naming, addition of HX, hydration (ketone formation ), addition of X2 , acidity of terminal alkynes, structure of benzene, naming substituted benzenes Electrophilic aromatic substitution, Halogenation, nitration, sulfonation, Friedel-Crafts alkylation & acylation Activating & deactivating groups, ortho, para & meta directing groups, chirality & enantiomers, srereogenic carbon, R &S configuration, E&Z convention for cis-trans isomers. Optical activity, properties of enantiiomers, Fischer projection formula, diastereomers & meso compound, stereochemistry & chemical reaction, resolution of racemic mixture Alkyl halides, nucleophilic reactions, the SN1 & the SN2 mechanims, elimination reactions, the E2 & the E1 mechanisms, substitution & elimination in competition. Chapter in Text (handouts) Chapter 1 Chapter 2 Chapter 3 Chapters 3, 4 Chapter 4 Chapters 4, 5 Chapter 5 Chapter 6 11 12 13 14 15 16 Naming alcohols, classification of alcohols, naming phenols, H- bonding in alcohols & phenols, acidity & basicity of alcohols & phenols, dehydration of alcohols, reaction of alcohols with hydrogen halides, other methods toprepare alkyl halides from alcohols. Oxidation of alcohols, aromatic substitution in phenols, oxidation of phenols, thiols, naming ethers, physical properties of ethers, the Grignard reagent, preparation of ethers Cleavage of ethers, epoxides, reactions of epoxides, cyclic ethers, naming aldehydes & ketones, synthesis of aldehydes & ketones, nucleophilic addition to the carbonyl group, addition of alcohols, addition of water, Addition of Grignard reagent , addition of HCN, addition of amines, reduction of carbonyl group, oxidation of carbonyl group, naming carboxylic acids, acidity, effect of structure on acidity, conversion of acids to salts, preparation of carboxylic acids. Nucleophilic acyl substitution, reaction of esters with base, amines,Grignard reagent and reducing agents, acyl halides, acid anhydrides, amides. Classification & structure of amines, naming & physical properties of amines Preparation of amines, alkylation of ammonia & amines, reduction of amides & nitriles, the basicity of amines,reaction of amines with acid derivatives, quaternary ammonium compounds, aromatic diazonium compounds, diazo coupling, azo dies. Chapter 7 Chapters 7, 8 Chapters 8, 9 Chapter 9 Chapters 10, 11 Chapter 11 Additional Notes Assignments Exams No assignments During this course, there will be a first worth 30 points and a second worth 30 points and a final examination worth 40.0 points. There is NO curve in this course. Please bring only pencils to the exams. Tentative Exam Schedule: 1. Two Majors (Class Tests): 2 x 30% = 60% I. First Exam: Mon March 19, 2007. II. Second Exam: Sat April 28, 2007. 2. Final Exam: May 26-June 4, 2007 40% TOTAL Cheating Attendance 100% Academic dishonesty of any form will not be tolerated. University policies on cheating and plagiarism (see Students' Guide) will be strictly enforced. Your attendance at all lectures is expected and essential to your success in this course. As a rule the student can't miss more than 10% of the lectures with reasonable excuses from the instructor, and another 10% with reasonable excuses accepted by the dean of science. If the student misses overall 20% of the lectures, then he or she can't enter the final exam and will fail the course with 35. Workload Graded Exams ……………. Participation No points, but students are highly encouraged to participate in the discussion. Laboratory None Projects None Disclaimer The instructor reserves the right to make changes to this course and its administration as reasonable and necessary. …………….