Spring 2013COURSE SYLLABUSCH-251: ORGANIC CHEMISTRY IHours: 3 Class Hours 4 Laboratory Hours 1 Recitation Hour 5 CreditsPre-requisites: CH-151 and CH-152Course Description: The relationship between structure and properties of organiccompounds are discussed, with emphasis on reaction mechanisms, stereochemistry,and synthesis. Laboratory work involves preparation, isolation, and identification oforganic compounds.Curricula for which the course is required/recommended: A.S. Degree Programs inLiberal Arts and Sciences (Science and Mathematics), Engineering Science, HealthSciences including Medical Laboratory Technician and those interested in careers in theMedical, Dental, Veterinary, Pharmacy, Chiropractic, and Physician fields, Forensics,Pharmaceutical Sciences, and Environmental Health.General Education Objectives: Use analytical reasoning and mathematical skills tosolve problems; integrate knowledge and skills in their major field and acrossdisciplines; use information management skills effectively for academic research andlifelong learning.Course Objectives/ Expected Student Learning Outcomes: The objective of thiscourse is to gradually and logically develop the relationship between properties andstructure of organic compounds. The lecture will begin by introducing general chemistryconcepts as they pertain to organic chemistry and will then describe drawing organicmolecules, functional groups, energetics of reactions, and stereochemistry. After thebasics are taught, students will learn reactions of specific functional groups and themechanism of the reactions. At the end of the semester, students should be able toperform multi-step syntheses and be able to work backwards starting from a complexmolecule. In the laboratory, the student will be introduced to the basic techniquesinvolved in the preparation, isolation, and identification of organic compounds.Texts: ORGANIC CHEMISTRY, 8THED., L. G. Wade, Pearson Education Inc., ISBN-13#: 978-0-321-76841-8WORKBOOK PROBLEMS FOR ORGANIC CHEMISTRY, Sarlo & Svoronos,Wm. C. Brown Publishers, ISBN-13#: 978-0-07-289968-9Lab: ORGANIC CHEMISTRY LABORATORY MANUAL, 2NDED., P. Svoronos, E.Sarlo, R. J. Kulawiec, Wm C. Brown Publishers, ISBN-13#: 978-0-697-33923-2QUEENSBOROUGH COMMUNITY COLLEGE which iseasier at queens collegeCHEMISTRY DEPARTMENTUse this as a guide for your next class This class is usally the same all around
Spring 2013CH-251: ORGANIC CHEMISTRY IMethods by which student learning will be evaluated: The general guidelines forassessing grades are as follows:o Examinations, Assignments and Classroom Performance 50%o Laboratory Work 25%o Final Examination 25%The distribution may be changed at the discretion of the individual instructor. Aside fromthe above, the student is mandated to take the American Chemical Society (ACS)assessment test which will be administered at the end of the semester. Ten percent ofthat grade will be added, as a bonus, to the student’s final course grade.Accommodations for students with disabilities: Any student who feels that he/shemay need an accommodation based upon the impact of a disability should contact theoffice of Services for Students with Disabilities in the Science Building, Room S-132(718-631-6257) to discuss his/her specific needs and to coordinate reasonableaccommodations for documented disabilities. Students should also contact theirinstructor privately to discuss their specific needs.Academic Integrity: Academic honesty is taken extremely seriously and is expected ofall students. All assignments must be the original work of the student (and partners orgroup, if applicable). All questions or concerns regarding ethical conduct should bebrought to the course instructor. “It is the official policy of the College that all acts orattempted acts that are violations of academic integrity be reported to the Office ofStudent Affairs (OSA). At the faculty member’s discretion and with the concurrence ofthe student or students involved, some cases, though reported to the OSA, may beresolved within the confines of the course and department. The instructor has theauthority to adjust the offender’s grades as deemed appropriate, including assigning anF to the assignment or exercise or, in more serious cases, an F to the student for theentire course.” (Taken from the QCC Academic Integrity Policy, 2/14/2005.)Attendance/Absence Lecture Policy: Attendance will be taken at every class. TheStudent Handbook states that you will be considered excessively absent from a courseand will receive a WU grade if you have been absent for 15% or more of the totalnumber of contact hours for your course. A WU is computed as an F in your GPA.Students who have valid excuses for missed classes should speak with their instructorand present documentation explaining the reason for the absence. Absences that havebeen excused at the discretion of the instructor will not be counted toward a WU grade.
Spring 2013CH-251: ORGANIC CHEMISTRY I If your class meets twice per week: you will receive a grade of WU ifyou have a total of 6 or more unexcused absences. If your class meets once per week: you will receive a grade of WU if youhave a total of 3 or more unexcused absences. If your class meets 3 or 4 times a week (summer session): you willreceive a grade of WU if you have a total of total of 2 or more unexcusedabsences.Laboratory PoliciesAll lab policies will be explained in detail by your lab instructor.Three (3) or more absences from the lab earn a grade of WU in the lab. A WU inthe lab results in a WU for the entire course. The first and last lab meetings are alsomandatory and will count against your total attendance. Policies regarding excused andunexcused absences will be explained by your lab instructor.There are no make-up sessions for missed labs. A full lab report is required for eachexperiment and is due the next class period. Your lab instructor will describe the formatfor lab reports, as well as requirements for entry into the lab. Students who arrive afterthe pre-lab lecture may not participate and will be marked absent.Safety in the lab is extremely important. Therefore, the ACS safety video must beviewed during the first lab session. A safety quiz must be taken and passed, and thesafety declaration sheet must be signed. A student that shows up for the lab, but whohas not seen the safety video and passed the quiz, will not be permitted to conduct theexperiment, will be considered absent, and will receive a zero for the lab. There will beseveral additional showings of the safety video during the first two weeks of classes. Astudent who has not viewed the safety video and passed the quiz by the third labsession will have accumulated 3 absences in the lab and therefore will not bepermitted to continue in the course. They may either withdraw or receive a WU forthe course.Required attire: Students MUST wear safety goggles in the lab at all times. Shorts andshort skirts, tank tops and cropped tops, sandals and open-toed shoes, untied long hair,and any type of food or beverage in the lab are forbidden. Students who fail to followthese rules will not be permitted to perform the experiment. They will be marked absentand will be given a zero for that lab.
Spring 2013CH-251: ORGANIC CHEMISTRY ILECTURE SCHEDULECHAPTER TOPIC HOURS*1 Introduction and Review 32 Structure and Properties of Organic Molecules 33 Structure and Stereochemistry of Alkanes 54 The Study of Chemical Reactions 45 Stereochemistry 56 Alkyl Halides: Nucleophilic Substitution 6and Elimination7 Structure and Synthesis of Alkenes 58 Reactions of Alkenes 59 Alkynes 310 Structure and Synthesis of Alcohols 411 Reactions of Alcohols 314 Ethers, Epoxides, and Sulfides 4* The approximate hours per chapter are guidelines and are at the discretion of theinstructor. The instructor is responsible for making assignments and schedulingexaminations. The Final Exam date is scheduled by the Registrar.
Spring 2013CH-251: ORGANIC CHEMISTRY I: LABORATORY SCHEDULELAB EXPERIMENT TITLE EXPT. # Page#1 Check-in; Lab Techniques; Safety Video --- ---2 Melting Points* 3.1 214 Steam Distillation* 4.3 385 Separation by Extraction 6.2 64Recrystallization of a Solid 6.3 696 Distribution coefficient --- handout**7 Equilibrium Constant* 7 808 Dehydration of tert-Amyl Alcohol --- handout**9 Synthesis of tert-Butyl Chloride* 13.1 15210 The Pinacol Rearrangement* 17.4 23211 Solvolysis of t-Butyl Chloride: 13.2 156A Kinetic Study12 The Grignard Reaction (Part 1) 14.1 17513 The Grignard Reaction (Part 2) 14.1 17514 ACS Exam15 Checkout* designates labs that have modifications to their procedures. See the next page titled‘Modifications to the Laboratory Procedures’** handouts are at the end of the syllabus3 Distillation - Simple and Fractional 4.1 & 4.2 31, 32
Spring 2013MODIFICATIONS TO THE LABORATORY PROCEDURESEXPERIMENT TITLE DESCRIPTION OF THE MODIFICATIONMelting Points Do Part B only but you will need to refer tosteps 4, 5, and 6 from Part A (p. 21) to do theexperiment.Steam Distillation For step 6 (p. 38), gravity filter into a pre-weighed, small beaker and remove the organicsolvent (CH2Cl2) under the hood using a hotwater bath.Equilibrium Constant Use half the quantity for each reagent (p. 80):therefore, acetic acid (7.2 mL) and n-propanol(9.4 mL) and switch to using a 50 mL roundbottom (instead of 100 mL) flask.Synthesis of t-Butyl Chloride For step 7 (p. 152), please check with yourinstructor first.The Pinacol Rearrangement For step 7 (p. 233), please check with yourinstructor first regarding the IR. Do the samefor step 8 regarding the NMR.,
Spring 2013DISTRIBUTION COEFFICIENT – LAB 6The experimental procedure is modified slightly from the one in the lab manual (p.56). Please read the lab manual first to understand the background information andimportant equations used during the experiment (p. 54-55).Procedure1. Place 1 mL of acetic acid into a 125 mL Erlenmeyer flask. Then add 59 mL of water.Therefore, the total solution volume is 60 mL.2. Take a 10 mL aliquot of the acid solution using a pipette and transfer it to a secondErlenmeyer flask. Add 2 drops of phenolphthalein indicator and then titrate with a 0.2N NaOH solution to a pale pink endpoint.3. Take another 10 mL aliquot of the acid solution from step 1 and transfer it to aseparatory funnel. Extract with 10 mL of ethyl acetate.4. Drain the bottom, aqueous layer into an Erlenmeyer flask, add 2 drops of theindicator, and titrate as before.5. Take a third 10 mL aliquot of the acid solution and transfer it to a separatory funnelbut now extract it twice, each time with 5 mL of ethyl acetate.6. Drain the bottom, aqueous layer into an Erlenmeyer flask, add 2 drops of theindicator, and titrate as before.7. Now repeat steps 3-6 but using toluene instead of ethyl acetate. Therefore theefficiency of extraction of ethyl acetate versus toluene can be tested.8. In the end, a total of five titrations will have been performed. This will leave behind~10 mL of the acid solution from step 1.9. To clean the burette (while still attached to the clamp), drain all the liquid. Then add10 mL of water and drain. Then add 10 mL of dilute hydrochloric acid and drain.Then finally add 50 mL of water, in portions, and drain. Do not unclamp the buretteuntil all draining and washing is completed.Questions1) Based on your data, is acetic acid more soluble in water or ethyl acetate? How aboutwater versus toluene?2) Which of the following organic solvents can be used in this experiment: ethanol,acetone, diethyl ether, methylene chloride, propanoic acid, acetonitrile? Explain youranswer (Hint: Look up the water solubilities of each compound in a reference bookbefore answering this question [e.g., the CRC Handbook of Chemistry and Physicsor use this lab manual, Table 6.1])3) Compared to acetic acid, is hexanoic acid (CH3(CH2)4COOH) more or less soluble inwater? Explain.
Spring 2013DATA SHEET: DISTRIBUTION COEFFICIENT – LAB 6Equiv. wt. of acetic acid = ______ g/mola. Volume of base required for first titration ________ mL = ________ Lb. Mass of acetic acid in the 10 mL aliquot ________ gFormula: massacid = (N x V)base x (Equiv. wt.)acidc. Volume of base required for second titration ________ mL = ________ Ld. Mass of acid left over in water layer ________ gUse the same formula as in (b) g AcOH in H2Oe. Mass of acid in ethyl acetate after a single 10 mL extraction ________ gItem (b) – item (d) g AcOH in EtOAc1 x 10 ml extraction(starting g AcOH in 10 mL aliquot – g AcOH remaining in H2O = g AcOH in EtOAc)f. Volume of base required for third titration ________ mL = ________ Lg. Mass of acid in water layer ________ gUse the same formula as in (b) g AcOH in H2Oh. Mass of acid in ethyl acetate after two 5 mL extractions ________ gItem (b) – item (g) g AcOH in EtOAc2 x 5 ml extractionsi. Distribution coefficient (Kp) of acetic acid in ethyl acetateItem (e) / item (d) Item (h) / Item (g)Kp (single extraction) ________ versus Kp (double extraction) ________
Spring 2013DEHYDRATION OF TERT-AMYL ALCOHOL (2-METHYL-2-BUTANOL) – LAB 8The synthetic procedure is identical to the one used for the dehydration ofcyclohexanol to cyclohexene (p. 123). In this experiment, however, two isomers will beformed instead of one.2-methyl-2-butanol2-methyl-2-butene2-methyl-1-buteneOHH2SO4OH2+H2O+Procedure1. Setup a simple distillation using a 100 mL round bottom flask as the reaction flaskand a 25 mL round bottom flask as the receiving flask. Keep the receiving flask in anice bath to reduce evaporation.2. Place 10 mL of water into the reaction flask and cool in an ice bath for severalminutes.3. Use a funnel to transfer 6 mL of concentrated sulfuric acid into a 10 mL graduatedcylinder (note: sulfuric acid is corrosive!).4. Use a pipette to transfer the concentrated sulfuric acid dropwise to the flask (fromstep 2) while continuously swirling.5. Slowly add 10.0 mL (8.1 g, d= 0.81 g/mL) of tert-amyl alcohol to the flask using apipette.6. Add several boiling chips and then heat the contents. Collect the distillate that boilsat 30-43 °C in a receiving flask (25 mL round bottom flask). Continue to collect aslong as the distillate is still flowing into the flask at temperatures above 43°C, butstop the distillation if it goes above 50 °C.7. Discontinue heating and transfer the distillate to a separatory funnel (using a funnel).8. Place 10 mL of 10% NaOH into the separatory funnel and swirl cautiously (releasethe vapor immediately).9. Separate the bottom aqueous layer and place in the designated waste container.10. Transfer the top organic layer into a small conical flask, dry the organic layer withapproximately 1 g of anhydrous sodium sulfate, and then cover the flask with awatch glass to prevent evaporation.11. Use a funnel to carefully decant the liquid from step 10 into a round bottom flask andset up a simple distillation (avoid the transfer of any crystals of the sodium sulfateinto the distillation set up as they contain water which should be removed).12. Collect the distillate in a pre-weighed dry vial that is kept in an ice bath to reduceevaporation. The bp range of the mixture should be 30-43 °C.
Spring 201313. Calculate the % yield of the mixture of alkene isomers.14. Add 5-10 drops of the distillate into 5 drops of 1% KMnO4 in a test tube. Record yourobservations. Add 5-10 drops of the distillate into 5 drops of 1% Br2/H2O in aseparate test tube. Record your observations.15. Check with your instructor first! Obtain a gas chromatogram of the isomeric mixture.Compare (if available) with pure samples of the two isomers formed. Calculate therelative % of the isomers formed.Questions1) Write the reactions that represent the addition of KMnO4 and Br2 to the two alkenes.2) Draw the full mechanism (with arrow pushing) for the dehydration of tert-amylalcohol that leads to the formation of both products.3) Explain the purpose of the following in the above experiment:a. Sulfuric acidb. Simple distillation – in step 1c. Sodium hydroxide extractiond. Anhydrous sodium sulfatee. Ice-cooled receiving/collecting flaskf. Covering the flask with a watch glass in step 104) Give all possible alkenes formed during the dehydration of each of the followingalcohols:a. 1-methylcyclohexanolb. 2-methylcyclohexanolc. cyclopentylmethanold. 3,3-dimethyl-1-butanol5) What alcohol would be the most appropriate starting material for the synthesis of 1-methylcyclohexene? Draw the reaction scheme.