CHE 241 Organic Chemistry (Learning Center) Instructor: Dr. Dexter L. Criss Exam #2 Student?s Full Name (Print) Student?s Full Name (Write) NOTE: Sharing of calculators is strictly prohibited. Violators will receive a ?0? grade for the exam! Remember, no hats or caps are allowed during the exam! Good Luck!!! I. Give the major mechanism (E1, E2, SN1, SN2) and product for each reaction. 12 points H OH H3O + CH2CH2OH H2SO4 H2O Br CH3O CH 3 C CH 3 CH 3 O CH3CH2S CH3 C O O H3C Br NH2 H2O OH H3O + OH Cl HOCH2CH3 CH3 C CH3 CH3 OH II. Give the product(s) or reagents for the reactions below. 30 points Br CH3 OCH2CH3 CH3CH2 C C Ph H2 P2 Cl H CH3 H CH3OH OH NaBr H2SO4 Ph C C H BuLi CH3Br 1. 2. Br HO - H2O NH2 CH3CH2NH2 Li C C CH3CH3 Cl CH3 H CH3 H OCH2CH3 Br Br Br CH3CH2O Br CH3 C CH3 CH3 O C Ph Ph Ph Br CH3CH2O Cl CH3 CH3CH2OH Br Br CH3O - OH H3O + CH3 CH3 CH3 CH3 CH3 CH3 III. Using the (E/Z) and/or (R/S) designation, give IUPAC names for each of the following. 8 pts CH3 BrC C CH2CH3 BrH3C H IV. Derive and determine the rate expression for the reaction below. 15 points Experiment Number [CH3Cl] [HO -] Rate (mol/L*s) x 10-7 Rate Change 1 0.0010 1.0 5.0 2 0.0030 1.0 14.9 3 0.0010 3.0 15.1 4 0.0030 3.0 45.0 Proportional Observation V. Consider the following pairs of structures. Identify the relationship between them by describing them as representing enantiomers, diastereomer, Cis/ Trans compounds or molecules of the same compound. 8 points CH3 H H CH3 CH3 H H CH3 C C HCl Br H HO Br C C ClBr H OH Br H H H3C H3C H Br OH H Cl l Br H OH H H H H VI. What is the major factor that affect(s): 3 pts SN1 SN2 E2 VII. Which reaction would you expect to react more rapidly by an SN2 mechanism. Explain. 3 pts Cl OCH3 CH3OH Cl Cl FCl OCH3 CH3OH F A) B) VIII. Which SN1 reaction would you expect to take place more rapidly? Explain. C CH3 CH3 CH3 Cl H2O C CH3 CH3 CH3 OH Cl ClC CH3 CH3 CH3 OHC CH3 CH3 CH3 Cl CH3OH 3 pts IX. Which reaction would you expect to react more rapidly by an SN1 mechanism. Explain. (a vs b). 3 pts A) B) Ph Br Ph Br NaCN NaCN DMSO Acetic Acid Ph CN Ph CN NaBr NaBr OCH3 OCH3 CH3CH2OH X. The reaction shown involves nucleophilic substitution. Please give a plausible mechanism of this reaction. 10 pts XI. Give the mechanism and product for the reaction below. 10 points BrH HO CH3 OH H2O H2SO4 Cl C CH3 H Ph HOH OH CH3 CH3 H2O H2SO4 IR Table
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