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This 18 page Study Guide was uploaded by Alexander Thompson on Friday September 30, 2016. The Study Guide belongs to CHM2211 at University of Florida taught by Castellano, Ronald in Fall 2016. Since its upload, it has received 11 views. For similar materials see Organic chemistry 2 in Chemistry at University of Florida.
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Date Created: 09/30/16
Pars.llano NA___E________________________ CHM 2211 F-2016 CHM 2211 Section 0786 Practice Exam #1 Solutions This practice contains 137 points worth of questions, so give yourself ~ 70 minutes to complete it. Important notes about the actual exam: You will be given two blank pages for scratch work. You must place your student ID on your desk for checking during the exam. There will be no regrades of exams that are written in pencil, erasable pen, or have white-out on them. Books, notes, models, and calculators are not permitted. Helpfinlformation: Degree of unsaturation (UN) = 1/2 (2C + 2 + N – H – X) On my honor, I have neither given nor received unauthorized aid on this examination. Signed: ___________________________________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 1. Answer the questions given below: 18 pts. a. Providthe IUPAC name of the molecule b. Rank the compounds in order of increasing shown below: 4 pts. acidity based on the indicated hydrogen atom. 3 pts. a. Classify the bold hydrogens as homotopic, d. How many C resonances are expected for each 13 heterotopic, enantiotopic, or diastereotopic hydrocarbon in its C NMR spectrum? 4 pts. in each case. 4 pts. 6 7 homotopic diastereotopic c. Shown below is a portion of a molecule that inhibits the enzymatic activity of -secretase by forming a carbonyl hydrate. Draw the structure of the hydrate. No mechanism is necessary. 3 pts. 2. Draw the structures of the cyclic hemiacetals that can be formed from the molecule shown below. Pay attention to stereochemistry! It is not necessary to draw a mechanism. 12 pts. O HO H OH (optically pure) 2 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 3. Draw the expected products for the following reactions. Treat each stereoisomer as a separate product (and draw it!). No mechanisms are required here! 35 pts. a. 3 pts. Br 1. Mg, Et2O 2. O Et O 2 3. HCl, H2O b. 6 pts. c. 6 pts. d. 6 pts. e. 6 pts. f. 8 pts. 3 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 4. Based on the molecular formula and NMR data given below, deduce the structure of the unknown. Answer the questions below to guide your thought process. 16 pts. a. Calculate the degree of unsaturation. 2 pts. b. Above each signal in the 1H NMR spectrum, write its multiplicity (e.g., doublet). 3 pts. 13 c. What do you learn from the C NMR data? Be specific. 3 pts. 4 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 5. Based on the molecular formula and 1H NMR spectrum given below, deduce the structure of the unknown. Begin by calculating the degree of unsaturation. Show your work/reasoning to guarantee at least partial credit. Your answer must cl early relate your propos ed structure to the spectrum (through chemical shift, integration, and multiplicity). 10 pts. 5 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 1 6. Based on the molecular formula and H NMR spectrum given below, deduce the structure of the unknown. Calculate the degree of unsaturation and provide thoughtful reasoning. 8 pts. 6 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 1 7. The following H NMR spectrum is of a dichlorophenol. From the chemical shifts and coupling patterns, match the spectrum with its correct isomer and explain your choice. Start by predicting the number and multiplicity of the peaks expected for each isomer. 14 pts. 7 Total Points:________ Castellano CHM 2211 S-2010 Exam #1 NAME:_______________________________ 8. Draw a complete stepwise mechanism for the following reaction. Used the curved arrow formalism and do not leave out any steps. You can ignore stereochemistry in this problem. 14 pts. 9. Propose a synthesis of the target shown. Show allreagents and conditions that you would use in each step. Restrictions have been placed on the carbon-containing building blocks that you can use (carbon-containing reagents are fair game). No mechanisms are required here! 10 pts. 8 Total Points:________
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