Practice Exams with Answers

Practice Exams with Answers - Chem 333 Practice exam II...

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Unformatted text preview: Chem 333 Practice exam II 1)What are the correct IUPAC name for the following compounds: A) b) Br 054W :3- ogqgm fimi—t’lmémuj’fl’tbwoo .t. CHM-m \ A. 1;: a» ’gftwhamtw‘f “5W EIEDW 1 AW 15.. Wmml 3! WW 45mm .., Ewec‘hfim ‘_ 0M Q H 0:43 :gijl—ig: HK 30 @HCHSJ “rig H30 H CH3 2—H CHC5 2- “-99% 3 ' H Identify the three structures that are lower in energy. a J b; Q . ‘8 ~ Are these identicai 111 energy? if one is lower if} energy identify which one. Ave, 9 (WDAt—ta \OWWS’MW Which of these five structures has the highest energy? 3) Circle which of the stluctures in the following pairs is more stable and list a reason Why. (If you think they have the same stability please say_ so. ) 4) Describe the relationship: Constitutional Isomers, conformational isomers, enantiomers, diasteriomers, same compozund or not isomers. 5 f 3 \l QMQWJW- 1 . 6) Ampicillin (shown below) is a widely used broadwspectrum antibiotic. Circle all the chiral carbons in ampicillin. What is the maximum number of possible stereoisomers‘? 1’} O _ _ 02 4 fl - Maximum#of81ereoisomers= m NH2 .. Amphicillin ’COZH (it; also Nit-ea M 7) Identify the product(s). If more than one product could be formed draw the major product. Show b) d} 8) Nucleophiiie Substition Reactions shott answers. a) Rank the following alkyi haiides aecmding to their expected reactivity (from fastest to slowest) with CH3OH 1n methanol. __'> S N 3— 6 Of +0. 0» W: «mst ‘t hOwWB m>a>a I b) Briefly expiain your choice for the one that reacts fastest: A Maker; MM MSJY 5W (Myocw‘w‘ _.__ 3:» \S 3 m3 WWW We} @ & N? :CEN: NETC {01‘4" Br omso 9 2° Wad-j “‘4 a) identify the major p1oduct formed. (Show stereochemistry when appropriate.) Potential Energy Products Reaction Coordinate h) Propose a structure for the transition state (I) given that this reaction is thought to go through an SN2 mechanism. (2) How does the concentration of {“ CN] effect the rate of the reaction? Circle ail the statements that are true. 10). Draw both chair conformations for cis l~chloro 4~t~buty1 cyclohexane. are 1° “3 t-BU = '-CH3 —R Conformation A Conformation B Which conformation is lower in energy A or B? Why? .. s . L B ,- JAq. \anx {Jada/Q 0km“? Rama/mm S PM on. Lg‘MM‘J WM 11. Stephanie added sodium hydride to compound I to make compound 2. Then she stirred the solution with 2~rnethyl~5—iodon2-pentene to make compound 3. Finally, she treated 3 with hydrogen (g) Pd in methanol. Identify the structures of compounds 2, 3, and 4. iii . Hscm—CECQH I{1%qu magi/1:12:30" Hztg) 1 —~—-—»> 2 -—«~——-—-—>~ 3 --—————-——~>- 4 w a j; k Pd CH3OH q i H%”C: ° \/M¢ E¢fi§/\¢L; 'l g \ c ‘4 l 5 3 ...
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