spring11sampleexam1key

spring11sampleexam1key - "\ CHEMISTRY 322bL/325bL 1::...

Info iconThis preview shows pages 1–10. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 10
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: "\ CHEMISTRY 322bL/325bL 1:: FIRST EXAM Print Last Name First Name January 27, 2010 First4 digits ofUSC ID _ __ _ _ -XXXX-XX Name of TA First letter of Last Name W Grader 1 (1-10). ________ (20) 11 (11-12). (6) 111 (13—14). _________ (10) IV (15-19).,_1_.1_ (25) v (20-21). _______ (15) VI (22). (12) VI (23). (12) W I will observe the rules of Academic Integrity while taking this exam. Signature Section 1. Multiple Choice. (20 points). 1. Circle the aromatic molecules. Assume that all structures are planar. 2. Circle the electronic configuration that corresponds to the cyclopentadienyl cation assuming that it is planar. ##llll 3. Circle the diene that will react the fastest with the dienophile below. 0 Diane + (ILH —————-—> Adduct (Circle the Diene Below) OEt Diene: / OEt / \ OEt \ / \ Name: k b 3 4. Circle the correct hybridization for the marked atoms in the structure below. Nitrogen ,/ Sp Nitrogen 3/»! SP @810 H 5. Circle the molecular orbital or orbitals (I — IV below) that are antibonding molecular orbitals in benzene. 6. Circle the compound below that should show the longest wavelength ultraviolet-visible absorption peak. 7. Circle the structure below that is the most stable. Assume that all species are planar. 0W0 Name: 4 8. The conjugated molecule 1,3,5-hexatriene (CH2=CH-CH=CH-CH=CH2) has 6 it molecular orbitals. Which of the three molecular orbitals shown below is the HOMO. 9. Circle the compound or compounds below that have degenerate molecular orbitals. Assume that all structures are planar. 10. Circle all the terms or phrases below that relate to reactions run under thermodynamic control. More Stable Producy Less Stable Product High Temmow Energy Transition State Low Temperature Equilibrium Section II. Nomenclature. (6 points). 11. Name the following compound. Br Br l/ 27 5: “"‘ +r; brflMebenwa Br 0 12. Draw the structure of p-nitroan‘lline. Section III. Drawing Structures. (10 points). 13. Draw all of the reasonable resonance structures for the compound below. Circle the resonance structure that would be the major contributor to the hybrid. V 77 ®\/.S.\ w Name: 6 14. Draw all of the reasonable resonance structures for the compound below. Circle the resonance structure that would be the major contributor to the hybrid. Section IV. Complete the Reactions. [25 points). Fill in the reactants, reagents, and/or products for the transformations below. Where appropriate, show the stereochemistry. 15. 16. 17. / H20 / H2304 M \ 18. / Brg —-—-—-———————————> CCI4/ Dark 25°C 19. _ ‘ W N {39 Br qu“ cm Qua» Br M/ -———————-—-> W Section V. Draw the Mechanism. (15 points). Draw the “arrow-pushing” reaction mechanism for the transformations below. Cl 20' )\ Clz Low Concentration ;\ High Temperature ~ci '——-—-’> 26! au- ' ~ 1 Ajfjfl‘mi Hf“? J“ ‘ch A \ fl n_ a M Jr 41' “t9 N 21 HBr Br Br r \ \ \ . / /\ // A //\I(‘%/+Nbér r——-L> “71 4-H- W69 A % DE? he, / 69/§ me; to W Name: 9 Sections Vi. Outline the Synthesis. (24 points]. 22. Outline an efficient synthesis for the product mixture below using the indicated starting material and saturated monohaloalkanes of 4 carbons or fewer as the only carbon sources. —————————> Br CH3 H CH3 0 ” B’ —«—————————-——> ‘ + ‘ H H Br H Br CH3 H CH3 racemic racemic Q (‘7 O Q lave/A D U Name: )4 1’3 Z; ’10 23. Outline an efficient synthesis for the product mixture below using the indicated starting material as the only carbon source. \/\/0H w“, Qgr ' I U "\ /\/\ou ""m t Mgr +63 0K9 _/\/ Nigg (gr “FEUOK‘ , ' ~ /\// //\/ \nv“ of” MIN * M5 60%;," /\/\%r / D Mmjap /\/\ou \/\/ H v @H l 9230?" v MVV + V in A/VV fly; / C3 7 4- + l) (gr (flwl 64w“ "We '3 [MMWQ/ ...
View Full Document

This note was uploaded on 03/15/2012 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

Page1 / 10

spring11sampleexam1key - "\ CHEMISTRY 322bL/325bL 1::...

This preview shows document pages 1 - 10. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online