ࡱ> PROa  bjbjxx 0N\N\ZZ$֜*~~~~ rrrUWWWWWW$f{re rrr{~ E7{7{7{r~ U7{rU7{7{n4 qZt A0֜9w@rr7{rrrrr{{yrrr֜rrrrrrrrrrrrrZ> : Exam 1: Chemistry 4524 24 Feb 2017 __/100 Your Name: ____________________________________ 1 pt Boxed and Addled by Alkenes (23 pts/1 pt per box) Fill in the products, reactants and/or conditions for the reactions below a) 1) +  Z only 3-hexene  Light & ______ b) propene + c)  + HBr 2-methyl-1-bromo-propane (mostly)  d)  + HCl e) peroxide  n CH2=CHCl  f )     g) +  h) Industrial route to ethanol   ___/17 including name Exam 1: Chemistry 4524 1.1 Boxing with Alkenes (continued) 2/6   uv light  i) +   j) +CH2I2  k)  + + 1.2. Stereo Entertainment Center (35 pts) 1.2.1 Terms of Organic Endearment ( 15 pts/1 pt each) 1) Im used to describe a 2 center stereochemical system where the groups of one sort are all on opposite sides. I sound almost religious but for my `r: ________________ 2) We have adjacent non-equivalent centers but we are the same (e.g. superimposable) even though we are mirror reflections of each other. We are _________ compounds (sounds sort of like a Japanese soup base as spoken by a Kansan) 3) Attack on an alkene from the same side: ___________ (sounds like something you should not do mispelled..) 4) Mirror images are not superimposable (rhymes with spiral): _____________ 5) Optical activity refers to: (circle your choice) a) rotation of plane polarized light by a molecular species b) whether a material absorbs visible light or not c) whether a compound is cis or trans d) molecules engaged in naughty, illicit liaisons 6) Letters defining specific handness of sugars and amino acids (Doc hates this one): _____ & ______ (2 pts) 7) Not mirror images, not superimposable. Chemically and physically different ________________________ 8) Weve got the same formula, same physical properties, but different chemical properties. We are a(n)________________ pair. 9) Name for a 50:50 mixture of left and righthanded stereo isomers of the same compound:_____________ 10) Name for the symbol: (d20 ___________________________ (two words, specifically) 11) Letter used by the Ingold-Cahn-Prelog system to indicate left handedness ______________(~ evil ) 12) Attack on an alkene that occurs during halohydrin formation: _________________(sounds like a relative) 13a)German word associated with R ______________13b) German word associated with Z______________ __/21 Exam 1: Chemistry 4524 (continued) 3/6 1.2.2 One-potato chirality (6 pts) Can use kits provided a) Assign the compounds below as R or S ( 2 pts each/ 6 pts total) Br=81, C=12, H=1  R S R S R S 1.3.3 Two-potato chirality (11 pts) Can use kits provided a) Determine whether the pair of compounds in the boxes below are diasteromers, enantiomers or meso structures. (2 pts each) [circle your answers] X Y  diastereomers enantiomers meso diastereomers enantiomers meso Assign the R/S character of the carbons at X and Y indicated above X is: R S 2 pts Y is: R S 2 pts   Jack Jack is: a) Z b)E c) D d) Threo e)syn f)poop     B Jill is : a) Threo (A=S,B=S) b) Meso (A=R,B=S) c) Z, A=R, B=S) d) Erythro , A=S, B=S) 2 pts  A ___/17 Exam 1: Chemistry 4524 (continued) 4/6 1.3 Alkyne world ( 40 pts) 1.3.1 Name or draw us! (2 pts each/12 pts total) C(C-C-C-C-Br _____________________________   3)   4) Draw 4-cyclopentyl-2-pentyn-1-ol 5) C(C-C-C-OH ________________________________ 6) IUPAC name for acetylene ______________________ 1.3.2. Alkyne Reactivity (2 pts/1 pt each) Which is the most acidic species? (circle your answer) H-CH2CH3 H-CH=CH2 H-C(CH H-C(C-C-C Predict the product(s) of combining: CH3C(CH + NaNH2 (in NH3(l)( 1.3.3. To and from alkynes Write out the classical two-step Bertholet process for synthesis of ethyne (1 pt) step 1 step 2 ___/15 Exam 1: PART 2 Chemistry 4524 : 1.3.3. To and from alkynes (continued) 5/6 Predict all the likely products if any: (1 pt each/5 pts total) NaNH2 in NH3(liq) CH3-CH Br2 NaNH2 in NH3(liq)  ` ``` (show all three possible) Cl-C(C-Cl NaNH2 in NH3(liq)  Alkyne Boxing Practice (20 pts/1 pt per box)   HC(CH then add   Only cis form +   4)  + 2HBr Solvent ?  5)   6)  7) +  E(trans) only  8) Br2 + indicate solvent Stereochemistry  9) H2O + __/25 Exam 1: PART 2 Chemistry 4524 : 1.4. Basic Alkadiene Finishing Touches 6/6 1.4. 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DPC!#?D C!#?@C C!?_`?`?`?+?+`?Sd+?d+Z   --"SystemOfk G-.  Arialv  ƒvvOfk--%\PRINT/2CompObjhObjInfo13Ole10Native.\%gg%a%a"SystemkOfk "---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q*''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   #?DCC!#? &DCC!#?3D@D!#?6DC!??I?_1517480685 @6eF0'O0'OOle PRINT58CompObjh   d * --"Systemfo G-.  Arialv ͘ޠƒvvfo- 2 Cl 2 cOl!2 EHl2 QNCHArialv* -8 ƒvvfo-2 d3H-2 CH-2 3H- 2 Cl 2 Ol!2 Hl-%]%]S]%----$]].,*]]-%]].,*]]-$]]]]-%]]]]-%%%%%%%%%%%"Systemofo "---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qObjInfo79Ole10Native_1486580165<eF0'O0'OOle ''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   #?PD@ D!#?)DD!#??D@D!#?$D!D!_?$D;D!#?!CH3_??DC!#?!CH3#?DD!#?:DD!? ?? ?_o?n? ?0! PRINT;>&CompObjhObjInfo=?Ole10Native.Z   --"Systemf G-.  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PRINTGJ%FCompObj/hObjInfoIK1Ole10Native2 Arialv  kvvf--%%%%%vN%NvN%+N%N"Systemf "---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   #?CD!#?@ DD!#?@.DD!#?@DDC!#?bDC!#?qD@D!#?lDC!?)LL?L)L?L??I?   nI _1390932646RNeF0'O0'OOle >PRINTMP?CompObjHh--"Systemf G-.  Arialtf wkttf--%t%Zt% ZZ% OO%E Z"Systemf "---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qq''[',Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   @#?ObjInfoOQJOle10NativeKu_1390932647TeF0'O@NOOle UD(D!#? D(D!#?D;D!#?@D;D!#?@D%D!?P??Z?Z M   --PRINTSVV6CompObj_hObjInfoUWaOle10Nativeb"SystemAf G-.  Arialt DPkttAf--%r}}%r%rrr%}}}%}}}%}}}%}}}"SystemAf "---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   #?pICC!#?(. DC!#?6CC!#?6C mC!#?aG>CC!#?6CpID!?-?8?8a8?8?8U8m   --_1486582226:ZeF@NO@NOOle mPRINTY\nCompObj}h"System fb G-.  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