Chem 2212 Exam 1 Key - Spring 2011

Chem 2212 Exam 1 Key - Spring 2011 - 810# CHEMISTRY 2212...

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Unformatted text preview: 810# CHEMISTRY 2212 EXAM 1 February 2, 2011 SCORE Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1' 1. (6 pts) Provide skeletal structures for all of the possible products of the following reaction. More boxes than are needed to answer the question correctly have been provided. You do not need to show stereochemist E/Z or R/S in our answer; 5 z: 3. 10. 11. 12. Total: Name: 2. (6 pts) Provide appropriate IUPAC names for each of the structures shown below: F Wag—tamin -174!er - ;. wage/‘91 you“, gr l‘Flum'o» 3-C3'W‘hflEfiflB-‘H-U'fiwflqklPropyl‘) bfiyum 0 HO * 750 W221 l bu Aué am- léopnp [9441»; «ac! 3. (4 pts) Provide the appropriate skeletal structure for each of the IUPAC names given below: m-tert-butylbenzaldehyde 5-isobutyl-2-ethylaniline Name: 4. (12 pts) Label each compound as Aromatic, Anti-Aromatic or Non-Aromatic. Write the appropriate label in the space provided. 6’ 03 N H 5. (10 pts) For the reaction below, provide the missing starting material(s), reagent(s), or intermediate(s). Where necessary, be sure your structures clearly indicate the correct stereochemistry. If more than one intermediate would be produced, draw each product (don’t worry about drawing both enantiomers of a racemic mixture, though). Wyn» “my” mJ-W‘N ‘ AND Atarlllalci Name: 6. (12 pts) Provide all of the products, consistent with Markovnikov’s rule, resulting from the addition of one equivalent of HBr to the following compound: You must provide the structure of each final product as well as the structure of the specific intermediate that leads to each product. You do not need to show stereochemist E/Z or R/S} in your answergsl. Intermediates Products Name: 7. (16 pts) Complete the following Diels-Alder reaction schemes by providing either the appropriate diene/dienophile starting materials or all possible reaction product(s). Show specific stereochemistry when appropriate: COZCH3 CHO COZH COZH CHO Heat #k/ + I l —> Name: 8. (10 pts) When bromine and water are added to 1,3,5-cyclooctatriene, three products are formed (shown below). Provide a detailed mechanism for the formation Of compound B. Draw the skeletal structure for each reaction intermediate formed during the course of the reaction. Use curved arrow formalism to indicate the flow of electrons. Name: 9. (6 pts) Propose a step by step synthesis of the compound shown below beginning with the indicated starting material. You may use any and all necessary reagents/reactants to complete your synthetic pathway: WA—> Name: 10. (9 points) Place the following lists of molecules in order as indicated: (a). Place in order of increasing Diels-Alder reactivity with acrylonitrile (shown below): CN W Acrylonitrile (b). Place in order of increasing maximum wavelength of light absorbance (lmax): Com Com 66% WW 11. (3 pts) Which of the following compounds is the most acidic? Circle your answer: \ \J/ Name: 12. (6 pts) Compound X, C14H2002, has the 1H NMR and 13C NMR spectra shown below. Propose a structure that is consistent with the provided spectra. Important IR data has been provided to aid you in your task. IR Peak Data: 3030 cm‘1 medium 1690 cm'1 strong 1600 cm"1 sharp, medium 1500 cm"1 sharp, medium Compound X: Proton NMR: E Doublet, 6H DcmbletJ 6H Doublet, 2H 9. Doublet, 2H Doublet, 2H Septet, 1H _ ...
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This note was uploaded on 10/05/2011 for the course CHEM 2211 taught by Professor Hubbard during the Spring '07 term at University of Georgia Athens.

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Chem 2212 Exam 1 Key - Spring 2011 - 810# CHEMISTRY 2212...

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