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3331 SP-11 Key exam 2 - CHEMISTRY 3331 Name EX Ll Second...

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Unformatted text preview: CHEMISTRY 3331 Name EX Ll: Second EXAM (print) Lust Dr. R. Thummel Last 4 digits of Peoplesoft Number 25 March, 2011 Please read all directions carefully. Write all answers legibly in the appropriate spaces and THINK about what you are doing. Give only ONE answer for each question (100 pts total). I . (20 pts) Carefully draw the structure of the compound whose name is given. Be sure to indicate stereochemistry where appropriate: (a) Z] ‘bromocyclodecene ._f”3 — (b) methyleneCYdObumne - (c) Z-4,6~climethyl—l,3,6—heptatriene [1/7 W \ (d) l—methyl—2,3-diehloro-1 ,3-cyelopentadiene C! a! “*3 H rst 2. (18 pts) A mono—substituted cyclohexene with the formula C6HgBr is chiral. In the top two boxes below draw and label both enantiomers of this molecule. Allylic bromination of these enantiomers leads to four structural isomers, two of which are achiral. In the second two boxes draw the two achiral products. C(,Hgl3r (Chiral) Enantiomer .or S ? (Circle one) R or©i7 (Circle one) N—bromosuccinimide (NBS) CaHxBrz (AChil‘al) CthBrz (Achirul) 3. (20 pts) The acid catalyzed dehydration of hydroxymethylcyclopentane gives a mixture of alkenes products. Give a detailed stepoby—step mechanism to explain the formation of the two products that are shown. Use arrows to show the flow of electrons. Draw any intermediates but do NOT draw transition states. Be sure to indicate all charges. (mom CH3 H4- + — H20 a @i (‘9 Mi C «Ole 1m 2, CM}! H W3 “2 W a» 4* ln the box below draw the structure of an additional alkene product that may be formed om 4. (12 pts) Starting only with 2—chloropropane, one can synthesize allyl isopropyl ether according to the synthetic scheme shown below. In each empty box draw the structure of the reaction products needed to complete this scheme. Y Cl NaOH t-BuOK (1 equiv) 0H NaOH (1 equiv) NBS @Oila WOY Allyl isopropyl ether 5. (10 pts) Consider the Fisher structure below. To the right of this structure are two Fisher skeletons with one substituent in place. Add the other 3 groups to give the same configuration 0f the same molecule. Is it R or S? E: Br CH8 CH3 W C\ /\ OtL Be m H\C>Q CH? C) CH} W ’Bv“ :t BY“ (3. (20 pts) For each of the following reactions, draw the structure of the principle organic product in the empty box. Give only one structure per box. Be sure to indicate STEREOCHEMISTRY where pertinent. (a) E“ ' Na Q Acetone CHQCH3 NaCN N CH (C) fig; 3 + NaCl + H20 OH D 3 t—BuOK , CH3 H t—BuOH ”“ Br H \‘i 7. Extra Credit 2! (6 pts) Draw the most stable chair conformation of S-Z—methyl-l .1» dibromocyclohexane. ...
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