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Exam 2 Key - NAME last first 810 CHEMISTRY 2211 EXAM 2 Be...

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Unformatted text preview: NAME last, first 810# CHEMISTRY 2211 EXAM 2 March 02, 2011 Be sure to read each question carefully. Partial credit will be assigned where appropriate. SCORE Onlx answers written in the boxes or on the lines will be graded. 1. (12 points) Name the following compounds using formal IUPAC nomenclature. 1- S 3. 4. (33“ 2" CYCLDPRDPYL - 3 —METH‘ILBU1‘HNE 5. 6. 7. H (I3 ) ZS)" IFCHLDRO "1— FLuomo L‘fCLCJ HEX/4114f; 8. 21¢, - DIMET‘H‘H— 4) 5" mnmonw. TOTAL IS 3R3— l* as zfl—Z—me‘neucvuotswrvn —3—((|s,25) ~Z~METHYLCYCL030TY L) as coo HEXANE’ 2 2. (10 points) In the accompanying box, draw (18, 3R)—l-ethyl-3-(methylethyl)cyclohexane in its most stable chair conformation. Calculate the total strain energy of this conformation given the provided steric strain energies. X 1,3-Diaxial strain ethyl 4.0 kJ/mol methylethyl 4.6 kJ/mol total strain energy: 0 gram IN EN 9:12:97 3. (16 points) Draw a detailed, stepwise mechanism using the curved arrow formalism to describe the following reaction. Identify each step of the mechanism. Brz, hv —> Hum“ NAME 3 last, first 810# 4. (8 points) Identify the following reactions as Addition, Elimination, Substitution, or Rearrangement. CI C12,,1V S DES—Fl TUTION \/\ _,.. \/\ + H30” 'ELIMINA-TIOM «smut Fi-Né—EMLE'N T” 5. (16 points) Label each of the chirality centers in the compounds below by writing R or S immediately adjacent to each chiral carbon. ‘u’ CH Cl H 3 /I< HO H H CH3 CH3CH2 BI" H 12 OH CHZCI CH—C—H2 Br H OH R Br 3 "’"HcH 3 HO H S 4 6. (12 points) Consider the molecule Cszlez. On the template below, draw a structure that is optically inactive because it does not have a chirality center. H it On the template below, draw a structure that is optically inactive because it is a meso compound. Illlllu- I I—C‘F I—g—F H On the template below, draw a structure that is optically active. Ilium I I—E‘F Iunllll 7. (12 points) Draw an asterisk (*) next to each chiral carbon in the following compound. You will lose credit for each chiral carbon not identified and each achiral carbon incorrectly identified as chiral. (H30)2N Calculate the total number of stereoisomers possible for this compound. 251 31 OH c—_‘“‘““"CCHa 8. 1.00 SD TIINSHITTINCEI Kl NAME 5 last, first 810# (14 points) Draw the structure for the following compound with molecular formula CmHqu based upon the IR and 1HNMR spectra. IIIDD i000 :nnn m‘lEMI'IIERI -I| lilfl 1.000 0; 3H d C 2H 5H — I I | .. I l I "l" 8 7 6 5 On the IR spectrum, circle and name two important absorptions. On the 1H NMR spectrum, label the four proton types from high field to low field as a, b, c, and d. Then, place those letters on your structure to correlate your structure to the 1H NMR spectrum. ...
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