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Exam2_key1a - Name First CWID Seat Number Chemistry 3053...

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Unformatted text preview: Name: First CWID: Seat Number: Chemistry 3053 Exam 2, 100 points Thursday, October 6, 2011 GENERAL INSTRUCTIONS: 1) Write name, CWlD, and seat number on this page 2) Check for 10 pages (including this one and the last page with the periodic table). 3) Sign the attendance sheet when you turn in your exam. 4) Keep your exam flat on the desk in front of you. You may only have a writing utensil and your model kits. EVERYTHING ELSE MUST BE PUT AWAY. No cell phones No calculators No electronic devices of any kind. Show Your Work. Be Specific With Your Answers and Write Legibly (if we can’t read it, we can’t grade it) GOOD LUCK When your exam is returned, your score will be on the last page. 1 Page Point Total 1) a) What is the structure of trans-1,4-dimethylcyclohexane. (4 points) 0)”) ’0 CA 5 b) Is trans—1,4—dimethylcyclohexane chiral? \j I! 2 (2 points) 0) Draw the two possible chair conformers for the structure you gave in part a. (6 points) 0% “A 3' ‘CW: (”I CH} Q43 d) Draw below (from part c) which chair conformer would be lower in energy, and therefore more stable. (2 points) CH 3 2 Page Point Total 2) For the following two reactions, identify which is correct and BRIEFLY explain why using the given pKas. (6 points) ii) CHsoH + NaH Na+ 'CH20H + H2 pKa H20 = 15.7 ' 5 {h pKa CH4=50 ’®\’\ (\0 m w M w 0A3 pKa H2 = 35 W H“ \D N? “SWS WW bum +70 Ww‘e ”CR3 3) For each pair below, state whether the two compounds are enantiomers, stereoisomers, conformational isomers, or identical compounds. (12 points) A) CH3 CH3 ‘ 5 ! molt3 H3c& h fiCH WW3 m! 6H OH D) Br l_3r . 1 l ‘ Br/\/'\/ WEI. 3 Page Point Total 4) Assign R or S at the stereogenic center for the following chiral compounds. (9 points) a) b) c) OH Cl ': Bl’ \Cl A/ N HSC CH3 LLL 5) Show the electron pushing arrows needed to go from the reactants to the products in the following reactions. (8 points) a) 0.. Hc+ Adm —-—-—» i + o O. b) %QJCH20H2CH20H3 ———~———» /1\ + CHgCHgCHgCHs 4 Page Point Total 6) Give the structure that corresponds to the following IUPAC names: (6 points) a) 2,3,3,4—tetramethylhexene 27/9 b) 3-bromo-4—Chlorohex-1-ene C\ M Bf c) 3—bromo—pentan-1 -ol B( 7) identify (by clearly circling) the stereogenic centers in the following compound. (10 points) HO OH OH H30 CH3 CH3 OH 5 Page Point Total 8) In the blank to the left for the structures given with each statement below, mark the correct letter answer (A, B, C, or D) for each question. (12 points) i) A Identify the compound with the highest expected melting point. A) B) C) D) /\/\/\ W —\:/:\ W ii) A identify the compound with the least ring strain. A) B) o) D) o a o A iii) C identify the hydrogenation product of 1-pentene. A) B) C) D) iv) A identify the compound that does not contain a stereogenic center. A) B) CH C) D) H30 CH3 3 / Br Q Am MOH CH3 v) E identify the functional group with the highest priority (assigning R and S) A) B) C) D) —F —| —0H -—8H vi) ,5 identify the electrophile. A) CH4 B) NH3 C) 3013 D) ‘OH 6 Page Point Total 9) a) Convert the sawhorse structure to its corresponding Newman Projection looking from CZ— CS. (6 points) E b 02-03 \3: Br / M 6H3 0" 3 CIA/3 b) Convert the Newman Projection to its corresponding sawhorse structure. (6 points) CH3 0) Draw the enantiomer of your sawhorse structure from part b. (3 points) 0A % H063 C“ Q ’\" '3 \X 3 C C\ d) Clearly label whether your structures from parts b and c are chiral. (2 points) wharf. WM 7 Page Point Total 10) For the following Newman Projection: (6 points) CH3 H Et H30 H CH3 a) Draw the highest energy staggered conformer: b) Draw the lowest energy eclipsed conformer: 9‘0““) 8 Page Point Total Extra Credit: (6 points) For the following conformers of (28,58)—5—(tert—butyl)-2—methyl-’I ,3-dioxane: \ CH3 'gfl/Q a) Identify (by circling) which is lower in energy. (3 points) b) Briefly explain your choice. (3 points) ‘ (Cl/Q Sweemws order er ‘06 600”“ microchm$ 9 Page Point Toté’il Scratch Paper Only — Nothing written on this page will be graded. - v 1 rat periodlc table of the elements 13 QQ sinker»: métals ymi meta 1 8 I. iifiiltfijm, / : lithium -— Hem“ Atomic 3 Number I Li— Symbol Am; nm -—'~‘—“:_°:“_L.. Vi’eight mmmwse 25 NJ” 2- 2‘ '24}.$' “r; V m .1 a 53mm w ":6 am R3: 3d A; Cd? we. Semimsinilim WW» 2 mm yzosmnm - Tm #3.": (is eiemflns by Le van Hare (Adm: synthetic elements Score: 10 Page Point Toté’il ...
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