Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil

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1 Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil Textbook and Materials What you must buy: Organic Chemistry 4 th Ed. Janice G. Smith, McGraw Hill. (Older edition is fine) Chem 7A and 7B Lab Manual Version 3 Robert Keil and Steve Joiner (bookstore) Subscription to TWO online services: smartworks.com (free), tophat.com ($20) You should buy: A lab coat and safety goggles. (Otherwise you ll be using a loaner) Getting in the Class Instructors have little control over who gets added to classes, or whether they can add extra students. If someone is not in attendance in the first lecture or lab, and have not written me beforehand, I drop them. The computer adds the next person on the waitlist. I have no control over who that is. If you are not on the waitlist, your chances of getting in are very low. If no one has dropped after the first day of lab, it is highly unlikely that any space will open up. I cannot get any more add codes, I cannot let you audit in case a spot opens up, there is no method to allow me to choose who gets in the class. I will give out add codes as they become available in the third week of class. Lecture Grade: Exams: Four each at 100 points = 400 points ~50% Weekly Homework: 5 points each = 75 points (Norton SmartWorks) ~10% Daily Quizzes 1-2 pts/day = 60 points (Top Hat) ~8% Cumulative Final Exam = 100 points ~13% Lab Grade: Pre-lab Quiz: 3-4 pts/day = 60 points (Top Hat ) ~8% Lab Sheet: 3-4 pts/day = 45 points ~6% Write-ups and Formal labs = 20 points ~3% Lab competency = 15 points (my assessment) ~2% 90% for an A; 80% for a B; 65% for a C; and 55% for a D. All exams will be cumulative. That is, anything you ve covered in the past can be brought back at any time. Obviously, each exam will mostly cover new material, but you cannot forget what you ve covered! There is no curve in this course. Everyone can earn an A or everyone can fail. You are not competing against your neighbor! No extra credit is offered. You must attend and complete the lab portion of the class, even if you are repeating the course or have taken a lab class at another school.

2 Office Hours My office is in PS-126. Office hours are before and after lecture Monday and Weds. I will be in (and out) on my office Tuesday 8:30 am-noon and some Thursdays. at (best); phone xtn 1765 Attendance and Dropping the Class: If you miss more than two weeks of class (or more than one exam), you will not pass! It is your responsibility to drop and make sure you are dropped. Pre-Requisites: You must have completed Chem 1A and 1B or an equivalent to take this class. Students who attempt to take organic chemistry before Chem 1B, or even concurrently with Chem 1B, have a 90% dropout rate! Course Website Smartwork.norton.com (free); search for Moorpark College Chem M07A Top Hat response system ($20); go to tophat.com; look for course Cheating: Cheating includes faking results and copying other people s answers during exams, and using unauthorized electronic devices on an exam. DO NOT USE YOUR PHONE DURING AN EXAM. EVER! Secret of Success in O-Chem: Organic chemistry is a lot like a foreign language. Study a little at a time, but study often. Unlike a lot of other classes you have taken, cramming before an exam will not work after the first few exams! If you find yourself falling behind, get help from a tutor or me. If you don t become familiar with the basics of the subject, you will fail the next semester. Don t let it wait! Try and form small study groups so that you can ask questions of your fellow students. Access Statement Students with disabilities, whether physical, learning, or psychological, who believe that they may need accommodations in this class, are encouraged to contact ACCESS as soon as possible to ensure that such accommodations are implemented in a timely fashion. Authorization, based on verification of disability, is required before any accommodation can be made. The phone number for ACCESS is and they are located on the ground floor of the LMC Building. Complaints? Chemistry Dept Chair Robert Keil Dean of Physical Sciences Julius Sokenu; AC 232, 8AM -5PM M Tr, 8AM - Noon Fri.

3 Student Learning Outcomes: Chem 7A At the conclusion of the course, students will be able to 1 describe how various organic molecules are used in medicine, industry, and the household and how their use impacts daily life and draw correct Lewis structures for a wide variety of main group compounds, identify hybrid and molecular orbitals utilized in bonding, and convert formulas into various three dimensional structural representations including skeletal (bond line) structures and resonance hybrids. 2 name cyclic and acyclic compounds containing alcohols, halides, alkenes and alkynes using the IUPAC (International Union of Pure and Applied Chemistry) system, name small compounds using common (e.g., iso, sec, tert ) prefixes, identify and name compounds containing common functional groups such as halides, alkenes, alkynes, carbonyl groups, alcohols, amines, aromatic rings and ethers. 3 identify conformational isomers, draw Newman projections and cyclohexane chair forms that accurately portray axial and equatorial groups, and predict which Newman projection and chair form will be most stable and least stable. 4 identify stereoisomers, label a stereocenter using the Cahn Ingold Prelog rules, distinguish between and define the terms enantiomer, diastereomer, meso, chiral and achiral, and provide examples of chiral molecules without stereocenters. 5 predict both the magnitude and direction of the polarity of organic molecules, identify intermolecular forces between organic molecules, and understand how intermolecular forces influence boiling point, solubility, nucleophilicity, and reactivity of organic compounds. 6 predict the course of any acid base reaction based on pka values and organic structures, rank common functional groups in order of their pka values, draw electron arrows to indicate the flow of electrons in Lewis acid base reactions, and identify various reagents that will quantitatively deprotonate an alcohol and an alkyne. 7 draw the mechanism and predict the products of inter and intramolecular nucleophilic substitution (SN) reactions, including stereocenter inversion during an SN2 reaction, racemization of stereochemistry during an SN1 reaction, and carbocation rearrangements. Students should be able to rank carbocations in the correct order of stability and list various groups in order of their nucleophilicity and use these skills to rank the rate of similar SN reactions that vary in the nature of the substrate. 8 use Zaitsev s rule to predict which alkenes will be most stable, label alkenes as E or Z using the Cahn Ingold Prelog rules, predict whether a given nucleophile will give predominately elimination or substitution in a reaction, draw the mechanisms of E2 and E1 reactions, and use this information to predict the major and minor products of substitution and elimination reactions of electrophiles bearing a leaving group. 9 draw the mechanism and predict the products of addition reactions to alkenes and alkynes including reactions that demonstrate the stereochemical ramifications of the addition of halogens and hydrohalogens (in the presence and absence of water), the difference between acid catalyzed hydration and hydroboration as methods of adding hydroxy groups, and the consequences of tautomerization to the enol products formed during hydration of alkynes. 10 draw the mechanism and predict the products of redox reactions of alkenes and alkynes, including epoxidation, stereoselective dihydroxylation, ozonolysis, catalytic hydrogenation, and stereoselective reduction of alkynes to cis and trans alkenes. Also, plan synthetic strategies using alkynyl nucleophiles. 11 draw the mechanism and predict the products of substitution, elimination, and redox reactions of alcohols, ethers, and epoxides, including the Williamson ether synthesis, dehydration reactions catalyzed by acids and other reagents, conversions of alcohols to alkyl halides using hydrohalogens and other reagents, tosylate formation, oxidations of alcohols to form aldehydes, carboxylic acids, and ketones, acid catalyzed decomposition of ethers, and the stereochemical ramifications of epoxide opening reactions in the presence and absence of acid catalysts. 12 explain the use of infrared spectroscopy and mass spectrometry in the determination of organic chemical structure, identify specific functional groups from IR spectral data, and use IR and MS data to make determinations about organic structures. 13 identify the causes and origins of the nuclear magnetic resonance (NMR) effect, correlate chemical shifts in NMR spectra with structure and predict the integrations, positions and peak splitting of signals in proton spectroscopy, and be able to both predict the NMR spectra.

4 Week of 19- Aug 26- Aug Lecture Monday Introduction to the course; online portions of the course; Review of Lewis structures Bond and molecule polarity; Electron arrows; Acid strength; Lecture Wednesday Lewis Structures; resonance forms; hybridization; bond Lengths; Lewis structures and electron arrows; 2- Labor Day Functional groups; intermolecular forces; Keq and pka; Predict acid-base reactions; 9- Finish/Review topics Chap 1-3; Intro to nomenclature Exam One (Chapters 1-3) Oct 14-Oct 21-Oct Alkane nomenclature; Newman Projections; Chair forms Chirality; Plane of symmetry; R/S designation (CIP system); meso Finish/Review topics Chap 4-5; Intro to thermodynamics and kinetics Review H, G, S; Energy diagrams; The SN2 reaction; leaving group; nucleophile, solvent, R group; examples The E2 reaction; Base strength; regiochemistry of E2; mechanism and electron arrows Stability of chair forms and Newman forms; Definition of oxidation Relationships between compounds; enantiomers and diastereomers Exam Two (Chapters 1-5) 28-Oct Finish/Review topics Chap 6-8 Exam Three (Chapters 1-8) Dec 9-Dec Nomenclature of alcohols and ethers; Synthesis of ROH and ROR; Dehydration reactions; Carbocation rearrangements Veteran's Day Addition of X2; hydroboration; halohydrins; organic synthesis Rate laws; catalysts; Nomenclature of Alkyl Halides; Physical properties of Alkyl Halides The SN1 reaction; stereochemical differences; leaving group; nucleophile, solvent, R group; deciding on a pathway The E1 reaction; solvent effects; Electron arrow mechanisms; Which reaction is it?; Organic synthesis POCl3; PBr3, TsCl; Epoxides; Opening epoxides in acid and base Nomenclature of alkenes; E/Z notation; Synthesis of alkenes; addition of HX; regiochemistry of addition Alkyne nomenclature; synthesis of alkynes; application of previous methods to alkynes; acetylide reactions Finish/Review topics Chap 9-11 Exam Four (Chapters 1-11) Review oxidation numbers; Hydrogenation; Partial hydrogenation; Epoxidation; Osmylation Lewis structures and properties of radicals; halogenation of alkanes; Final: Weds, 12/ am Ozonolysis; Partial vs complete oxidation of alcohols; LiAlH4 and NaBH4 Allylic halogenation; Polymers

5 Week of Lab Monday Lab Wednesday 19-Aug Check In - Worksheet Check In- Worksheet 26-Aug Physical Properties of Compounds: Melting Points Review 2- Labor Day Physical Properties of Compounds: Melting Points 9- Recrystallization of Benzoic Acid Recrystallization of Benzoic Acid 16- Acid-Base Extraction of Benzophenone and Benzoic Acid Acid-Base Extraction of Benzophenone and Benzoic Acid 23- Stereochemistry Model-Building Lab Stereochemistry Model-Building Lab 30- Infrared Spectroscopy Infrared Spectroscopy 7-Oct Synthesis of 2-Ethoxynaphthalene: An SN2 Reaction and Lab Notebook Exercise 14-Oct Gas Chromatography Gas Chromatography Synthesis of 2-Ethoxynaphthalene: An SN2 Reaction and Lab Notebook Exercise 21-Oct Simple and Fractional Distillation Simple and Fractional Distillation 28-Oct The Blue Bottle Reaction Mechanism The Blue Bottle Reaction Mechanism 4- TLC and column chromatography of a spearmint oil mix TLC and column chromatography of a spearmint oil mix 11- Veteran's Day A Grignard-like Organic Reaction in Water 18- A Grignard-like Organic Reaction in Water Review 25- GCMS day - Finish Grignard lab GCMS day - Finish Grignard lab 2-Dec Check Out Check Out 9-Dec Review for final Review for final

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