Exam 1 Practice KEY

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University of Delaware *

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321

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Chemistry

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Jan 9, 2024

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12

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14. (10 points) Here are spectra for two of the compounds listed below. Draw the correct compound next to each spectrum. ---------------------- 13C NMR : - 200 ~ ~ 180 160 ~ ~ "s0 ~ © ; 5 IR E : 3080 2000 1500 1000 500 i 5 0O OU o oTTo O"% IGNORE KEY FOR THIS - IT’S MISSING
12. (12 points) Here are 13C NMR and IR spectra for compounds from the list below. Draw the correct structure next to each spectrum. The same compound could be used more than once. ----------------------- *, a) 2C NMR : E ' : ' ' ' ' . O ' ' NSNS . 1 ] ' ' 1] 200 10 10 s ' 0o f T NN EEmEmEmssssEsE.----- b) ~\ p \J VAR 3\ N IR | e Vo a [ N \ / | OH o B - . - = —— ____‘ —— ——~ . - .. . ’.-------' ~ zdoo .. 2000 . 1500 1000 . 500 | ----------------------- é/: ----------------------- 11. (10 points) Here are spectra for two of the compounds listed below. Draw the correct compound next to each spectrum. ------------------------ o : ; 200 ° "150 " ! 100 ° 50 ° ' 0 ".'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.'.‘ a‘ ; 200 ' ' ! ' 100 T T v O 2 TTTmmmmmmmmmmmmmmmmmsss AN /\I/ /\( /\"/ /\n/OH OH 0]
7. (4 points) Here are '3C NMR spectra for two of the compounds listed below. Draw the correct compound next to each spectrum. 100 200 Sk 150" = 100 ---------------------- ----------------------- ---------------------- e E e e -----—- ---------------------- 8. (8 points) Each of these spectra represents one of the compounds listed at the bottom. Draw the correct compound next to each spectrum. The same compound could be used more than once. e e a) - \ . AR AY WA Y ARE \ h"ln||. \ / l( ' | | | 1] ( | | |} i { ' . | | [ ‘H' | o [f H \J / ! ....... 2000 < 1500 . 1000 _ 500 | * . . 1 ] H 1 ] : . L} 150 " 100 50 = o ---------------------- R g ---------------------- ---------------------- Ve mmmmmmm----? ----------------------
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8. (6 points) These '3C NMR spectra correspond to two of the compounds below. Draw the correct structure next to each. 13C NMR premmnsnsnsnsaee , 200 "150 T 100 T " 50 T ) e e mmmmmeeeeeeeeaaaaat ' 13C NMR prenmmmnsnsanns : NN 200 150 100 50 g rrommemmemreeeneeeset
10. (12 points) These spectra represent compounds from the list below. Draw the correct compound next to each spectrum. The same compound could be used more than once. 15C NMR a) 200 S o150 100 50 IR \ oV N\ . -\' 2 N\ N\ {" \ //' | \[ )/ Wl [, 8] |fl ) b) | | [ | 'U) o Wf A | ........ 3000 . . ... ..2000. . ‘. . 1500 . . 1000 15C NMR c) 200 150 100 50 . 500 --------------------- \i --------------------- ---------------------- --------------------- ---------------------- 1. (12 points) Here are the IR spectra for two of the compounds shown below. Draw the appropriate compound next to each spectrum. | Y ]1 [ | |{r11fi'\ / | { | PV | H | / A 3000 2000 1500 1000 \ L A n ol ; | 1/ I| 4 i | M 1 | l K* | I H] |1 I | | |P i gw U l AW _3000 . 2000 . ~1500 . 1000 --------------------- --------------------
1. (12 points) Here are the IR spectra for two of the compounds shown below. Draw the appropriate compound next to each spectrum. -------------------- a) i o < y— P - --------------------- 3000 . ... 2000 . N 1500 . 1000 . 500 - 4 b) -------------------- r han's ' TV P . 4 avYavl \.S A \ { \ 2 y J 3000 . . 2000 . 500 O> >= --------------------- OH O O /\O/\ /\O/\ /\0/\ /\) /\/”\OH /\O)I\ 5. (10 points) Draw Newman projections looking down the C2-C3 bond of the three staggered conformations of this. Circle the lowest energy one or ones. ----- . e ~ . ------
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5. (16 points) | have drawn in one conformation for this compound (it is repeated at the 360 degree mark). a) Please draw in the other staggered and eclipsed conformations in the small boxes. b) In the large box draw a curve showing the relative energies. You DO NOT need specific values -You DO NOT need specific values - all you need to know is that a Ph group is larger than a CH3 group. Based on that you can make it clear which energies are higher and lower or the same.
5. (18 points) Here are the energies (in kcal/mol) for staggered and eclipsed interactions for CH, CC, and CO bonds. bonds CH/CH CH/CC CC/CC CH/CO CC/CO eclipsed (0°) 1.0 1.3 3.0 1.6 3.6 staggered (60°) 0.0 0.0 0.9 0.0 0.2 OH a) Here is a Newman projection of one of the staggered conformations of the molecule above, looking down the C2-C3 bond. Draw Newman projections of the other two staggered and the three eclipsed conformations (in order). CHs HCH3 CH; HsCCHs CH4 HOCH; OH H,C HO CHs OH - CH T H {H H% H {H H H CHj OH = 0.2 4.2 0.9 5.6 1.1 5.9 b) Calculate the relative energies for each of the conformations and write them below each conformation.
8. (16 points) Label the relationship between each pair as identical, constitutional isomers, stereoisomers, or unrelated. a) cyclohexane /\/\/ b) Zlfl w d) ‘é'\/\/\ \/\/ | --------------------------- constitutional isomers """" . 3 ; ;;L;;};';L;;L;""g Bl 8. (16 points) Label each pair as identical, constitutional isomers, stereoisomers, or unrelated. a) /\/(/ \/d/ Br b) \/\/\ E-2-bromo-2-hexene : LS --------------------- a @ = 8 --------------------- w @ (0] o w O 3 @ w --------------------- constitutional isomer 1 ceadlaaar --------------------- --------------------- --m--' constitutional isomer 1
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6. (9 points) On the left | show three planar cyclohexane rings. On the right | show chair conformations. Label each of the chairs as X, Y, Z, or "other compound". The same answer may be used more than once. \\\\\\\ \\\\\\\ &Q/ "”I// ""I// ""I/, I i E ------------- X Y Z a)i other | b)i z i o X i ‘campound.’ e . Ot . 4. (3 points) On the left | show three planar cyclohexane rings. On the right | show chair conformations. Label each of the chairs as X, Y, Z, "other compound", or "meaningless drawing". The same answer may be used more than once. \\\\\\ ‘\\\\\ U 6. (10 points) Draw pictures showing the two chair conformations of this. Circle the lower energy one or write "same energy". ~ _L.--el - B A . R . p [} ' [ » [ . . [ ' [ ' O : : , i | [} ; 0 \\\\\ I,,l, ': . . . . * -~ Ll ~ ~ - ------- 5. (12 points) Draw clear pictures showing the two chair conformations of this compound. Circle the more stable (lower energy) conformation, or write "same energy". ---------------------------------------------------------------- . ------ - . s P L LI TS ..--I--I----II--I' L L L L L L LS EA s s sEssEEs s e s s e s e e s e e e . mm? - -~ - ------- 4 - 4 -
4. (5 points) On the right | show the orbitals for the molecule on the left. Label the indicated orbitals as s, p, d, f, sp, sp?, or sp°. cnsses?’ e 4 1. (4 points) Here are the atomic and hybrid orbitals for the compound on the left. Label the indicated orbitals as s, p, d, f, sp, sp?, or sp>. 5. (4 points) Here are the atomic and hybrid orbitals for the compound shown on the left. Label the indicated orbitas as s, p, d, f, sp, sp?, or sp°.
2. (4 points) Draw line angle structures for each of these. CH3;CH,OCH,CH,CO,H 2,5-dimethyl-4-propyloctane 0: /\6/\)J\6/H 3. (6 points) Give the systematic (IUPAC) name for each of these. 4-ethyl-2,2,5-trimethylheptane 3-ethyl-2-methyloctane 1. (9 points) Draw line-angle structures of each of these. H H HaCACl ‘O : 3 Qe Qi Z-1.2-dichloro-2-hexene H"T CH; H—C—C—C—C—C—H CH, 7Y 7 | HHH H Ho \X@,; )\/”\ C'\)\/\/ 2. (9 points) Give the systematic (IUPAC) name of each of these. Cl T T 2-chloro-4-methylheptane Z-3-chloro-4-methyl-3-hexene cis-1,3-diethylcyclohexane
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