Shea-Mid-I-Test-Key

Shea-Mid-I-Test-Key - 1(a Draw a valid Lewis structure for...

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Unformatted text preview: 1. (a) Draw a valid Lewis structure for the following molecules: at? 00 (no 03 CZQ‘W (BEES - 00 CD a» (+3 NO; :: k) :1 (b) Draw resonance structures for the following molecules; . . o o "10°C: :: I, A.“ \\ 0:6) _, e \, ,é a, N o o I U 9“ (3—6 H SUE:— C.‘ (c) Draw all important resonance structures for the anion shown below. In the box below, draw the resonance hybrid. Resonance Hybrid 2. (a) In the following Bronsted-Lowry acid-base reactions: a) Identify the acid and base (in boxes below reactants). b) Draw products (large box). c) Indicate direction of equilibrium by clearly circling the appropriate arrow. --9 ©—~‘ HaC-CECH + /N\ H30 .. CH3 .— cams- §§< 2 ’18 O 'E 9 (5K “UVQ \G-H? (b) In the following Lewis acid base reactions, a) Identify the Lewis acid and Lewis base (in boxes below reactants). b) Draw products (large box). 3. (a) Draw the skeletal fonnula (i.e. M) from the following condensed formula- CH3CHCICH2CH(CH3)2 (LL M (b) Convert the following compound from a condensed formula to a skeletal formula. CH3CH2C(CH3)2CH2CH(CH2CH3)CH2CH(CH3)2. Nflfid 4. Identify in the space provided if the following pairs of compounds are structural(constitutional) isomers, conformational isomers, stereoisomers or none of the above. C: c;\ 0 Cl ' C ' C and “"H ‘MH M New ; (:ECI CI H CH20H3 F ‘ H30 CH3 H5,ch .- and F H H CHECH3 H CH3 5. Assign formal charges to the atoms in the molecules below. 6: C9 :5: H . 20H H—C=I{I—c—H @ N‘“ H u | . ” /C\ H v H .CEN—C_H H30 CH3 6. (a) Assign the hybridization state of the labeled carbon atoms. /\ 1 \ mama (b) Indicate how many hydrogens are attached to each of the carbon atoms. Place your answer next to the labeled carbons. (c) Indicate the type of carbon (1°, 2°, etc.). Place your answer next to the labeled carbon. C" H CH3 H H I l l l Hmc-mcu-c-uc-— l l l l H CH3 CH3 H H 7. (a) Rank the acidity of the labeled protons in the following molecules from highest to lowest. 0 ll OCHQCHCHZC H2‘C—O \ ‘ I I I H q 3 H a, 3 H b Ha Hb Hc Highest -------------------------- ——Lowest Ha C"_-=...C---§-|c U Ha. Ha, H t. Hb Highest —————————————————————————— ——Lowest (b) Circle the compound that is the strongest Bronsted—Lowry acid. A. CH CH OH . CHZCICHZOH C. H3 2 D. ClCHzNH2 E. CH3CH3 (0) Rank the following compounds in the order of decreasing acidity. o 0 ll H . A- CH30H20H3 B. ,CH3COH c. CH3OH D. FCH200H b) P», C y A Highest ————————— ——Lowest (d) Circle the stronger acid. OH OH A. b B (e) Circle the strongest base. A. CH3' B. NHZ' C. Cl' D. OH" E. I' (f) Rank the following in order of decreasing basicity. Place the letter of the base in the answer box. 0 Cl H _ Ar CH300 B. CH3CH20' c. CH3CH—o‘ Most basic --------------- --Least Basic 8. (a) Circle the compound with the highest boiling point. 0 II A. CH3CH20CH20H3 B. CH30H20H200H20H3 c. (b) Identify the major functional group in each of the compounds below. Place your answer in the box. (b) Give the IUPAC (systematic) name for the following compound. 1 e (CH3)2CHCH2CH(CH3)CH(CH3)CH2C(CH2CH3)3 1 y _ i 5 7C (e) Give the IUPAC (systematic) name for the following compound. CH CH 3 3 | CH \CH 2 l HBC\CH CH | CH3 3 10. (a) Rank the indicated conformations in order from highest to lowest stability. CH3 CH3 H CH3 H H H CH(CH3)2 g H H CH3 H CH3 H CH3 H CH(CH3)2 (H30)ch A. B. 0. Most Stable -------------------------- «Least Stable (b) Given the three Newman projections drawn below, rank them in order of decreasing stabiiiry. H H CH3 CHZCHS H30 H H CH3 0H20H3 CH OH H H3C 2 3 Else H H CH3 A. C. B. Most Stable ---------------------- ——Least Stable (c) What is the name that describes the relative position of the substituents A and B to each other in the following conformation? A . Q; (d) The graph below shows the energy changes that occur during rotation around the C—C bond indicated in compound X. Circle the letter(s) on the graph that corresponds to this Newman Projection. CH3 OH I l“ Hsc—(‘E—CHz—CH3 H I H/ CH rotation CH3 H rotation C\‘X> C \ +3 Maia 3 ...
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This note was uploaded on 04/26/2008 for the course CHEM 51A taught by Professor Sangodkar during the Fall '07 term at UC Irvine.

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Shea-Mid-I-Test-Key - 1(a Draw a valid Lewis structure for...

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