Fall03Test1 - NAME SS# XXX—XX— Introductory Organic...

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Unformatted text preview: NAME SS# XXX—XX— Introductory Organic Chemistry 030.205.01 MIDTERM EXAM #1 October 14, 2004 Circle Your TA ’s Name Ciby . Carter Gizem Dan Michah 7 Alvin Kristen Andrew C. J. Gary Bill Ed Meghan Don’t Know TOTAL 1) For each of the following pairs of compounds, place a circle around the conformation that is more stable: (2 pts each) Me Me Me H H H H H H $ H a) H Me b) OH OH HOflH H fiH H H H H c) H OH 2) Consider the following acid—base reaction: 9 e H—CEC—H + NH2 v——— H—CEC Which side of the reaction does the equilibrium favor? (2 pts) a) the right side b) the left side c) both sides equally d) cannot tell without more information 3) Choose the drawing below that is not a resonance structure for l-nitrocyclohexene: (2 pts) 9 e 9 9 ore/p o\ /0 039,0 0\ o 4) Consider each of the following compounds below. Place a circle around each compound that you'expect will be optically active. (8 pts) OH Et CH3 H @ Me Mega HO H Me H H Me H OH .x\ Me Cl Me Me , / / H’r'czc:c\ /l\/ Mgé'czczq H Me 5) Consider the following compound: CI \QNCI Me a) Draw both chair conformations of this compound. (2 pts each) b) Circle the chair conformation that is more stable. (1 pt) 6) How many lone pairs do you see (that are not drawn) in the following drawing: (2 pts) & @2 m3 Q4 m5 N A 7) For each of the following pairs of compounds, determine whether the compounds are a) constitutional isomers b) enantiomers c) diastereomers d) different representations of the same compound: Use the letters above (a, b, c, or d) to answer each of the following problems: (2 pts each) CH3 CH3 H OH HO-—H HO H H——-OH H OH HO——H CH3 CH3 Relationship: Et HO H H OH HO H Me Relationship: Et H OH HO H H OH Me /OKH/ OI % Relationship: (:DH Relationship: B13 Relationship: Cl ~‘\\\ 0," t “m, \\\“C‘:< Relationship: 8) For each pair of compounds shown below, choose the more acidic compound: (2 pts each) a) /U\ /\ O b) /U\NH2 AOH 0:0: H—CEC~H d) NH3 H23 9) Consider the following drawing: How many stereocenters do you see? (2 pts) a)4 b)5 c)6 d)7 10) How many stereoisomers can be drawn of the following: (2 pts) OH Cl M OH @3 m4 Q6 @8 11) How many stereoisomers can be drawn of the following: (2 pts) OH 2y ‘OH a)1 b)2 c)3 d)4 12) In each compound below, there is one stereocenter. For each compound, determine the configuration of the stereocenter. Place your answers in the space provided: (2 pts each) OEtgH Mm Configuration: NH2 /\/ Configuration: CI Configuration: 13) Alkyl groups are because of . The words that best fill in these blanks are: (2 pts) a) electron withdrawing / resonance b) electron donating / hyperconjugation c) polar/ H—bonding d) unstable/ resonance 14) Name the following compound: (6 points) OH W 0 NAME 15) Draw the structure of E-4,4,5—trimethylheX-2-en~1—amine. (4 pts) 16) Draw all significant resonance structures for each of the following compounds. Show your curved arrows. (7 points) QM 17) Using a Newman Projection, draw the most stable conformation of the following compound (looking down the C-C bond indicated by the arrow): (3 pts) \i/ Me 18) For each labeled carbon atom in the molecule below, identify the number of H’s attached, the hybridization state and the geometry: (1 pt each) a b C\ \ N # of H's attached # of H's attached __ # of H's attached a) hybridization state hybridization state __ C) hybridization state geometry geometry _____—_ geometry 19) For each of the compounds below, draw its enantiomer: (2 pts each) 0 H H OH H OH HO H 3) CH3 20) For each of the following pairs of ions, place a circle around the ion that is more stable: (2 pts each) wk % b)/.& /K9/ QM M Extra Credit: What is the common name of ethyne? (1 pt) H—CEC—H Common Name: ...
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This note was uploaded on 04/07/2008 for the course CHEM 205 taught by Professor Klein during the Fall '03 term at Johns Hopkins.

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Fall03Test1 - NAME SS# XXX—XX— Introductory Organic...

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