Test_II_3331_F - .._,-fi.-.“L“l \Nlm “53":L...

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Unformatted text preview: .._,-fi.-.“L“l \Nlm “53":L Second. Exam Name (PRINT) Last, First Chemistry 3331 Signature October 19, 2001 ' ' “SSE? Please circle the nameof your professor and class time where appropriate. Dr. Bean (TIT h 10 AM) Dr. Cai Dr. Bean (T/Th 5:30 PM) Note: Present your student ID when you return the exam booklet L NOMENCLATURE (12 pts; 4 pts each) Give +he acceptable lUPAC name for each of ihe following compounds. Be sure To Indicate the STEREOCHEMIST—RY where appropriate. [In .. 2} _ .. H--=--ICI CH20H3 m It. Facts: Total = 34 points 1. Piece the foilowing halides in order of their increasing reactivity in the SM process (1=Ieast reactive: 3=most reactive). (3 pts.) CH3 CHzC' 0: CH3 : ‘cr 2. Place the following compounds in order of increasing bond dissociation energy for the bond indicated by the arrow. (1=lowest BDE, 3=highest BDE). (3 pts.) CH-CH3 CHQCHQ fl CHEG H3 H 3. Place the toiiowing carbahions in order of increasing stabiiity (1:1east stable, 3=most stabte). (3 pts.) (3 D 4. Place the following haiides in order of their increasing reactivity in the 8N2 process (1 =ieast reactive. 3=most reactive). (3 pts.) E] E] CI I EZ I 1 E] _ 5. Place the following aikenes in order of increasing stability (tzleast stable 3=most stable). (3 pts.) 6. Label the pairs of molecules as identical, enantiomers, diastereomers, or structural isomers. (9 pts.) CH3 CHQCHQ Br OH HO Br a. HO CH3 HO CH3 CHQCHg CH3 OH or H OH 9H3 QOQH H02C.‘ é 40H H0“ 5 ACHB ! l C B Hscy'E‘Br GHsCHa CHQCHa 7. Using Fischer projections, draw all stereoisomers of the compound shown below. Please place the CH20_H group at the top in your projections, and assign each structure a number. Circle all pairs of enantiomers. Identify one pair of diastereomers using the assigned numbers. (example: #22 and #24 are diastereomers) (14 pts.) Br PH2-:C——?H-CH3 OH OH OH ill. REACTIONS (30 pts: 5 pts each} For each of the following reactions or series of reactions, please draw the Final Major Organic product, or reactant in the box provided. Be sure to indicate the Stereochemistry where this is pertinent. in multipfie step reactions, you may place intermediate products below the reaction for paniei cerctit. OH 1-} H2804 f i i t 9H3 g e e H - Br Na 2} ! We» H .I-E-I-fi F I CHZCHS 3) + Nal 1) NBS, light --—--————-—-—-—+ 2} NaOH 6 @ CHSCHEO Na r____r_________fl IV. Mechanism: “JO points The foliowing reaction yields a mixture of products. Provide a clear mechanism for the formation of A , B and C. Use curved arrow notation to indicate "eieotron flow!" and show ail intermediates and formal charges. OCH H30 CH3 H30 CH3 H30 OCHa H C 0:: w, Br oer-13 CH3 3 3 CH OH Heat ’ + + A B C V. Synthesis: 10 Points From cyclohexane and any inorganic reagents, synthesize the compound below. Q Emzmm memzjflo \ vmaogo 0393 01 Em mrmZmzam 28; F W E. :5 Eu fl. 5m 55 . E: . 5 5 a; E» E. E» 5; 3mm“ > a . X , Hf .— n u I x _ I Im 53m. ....... -_ _.. a _ . ‘83. £38 a. a _ _ _. .fl... a. a H. \H m m u m m ._o u 5 mm a , M m y. w o z @ m 2m [mgfilfimm # \ . 3.2 E: r383 $32.53th 3.3. 3 E . g _ 6 u a 6 M 2m am < ,, _ n_. E . 5%: 5D ii: - “$3 3.2% .5-|E1..mfi...mm.l.i . nf mm mm m.» . um. wm no N am u I Om < O... 2.: 1m 00 .2. O: N: .n -..w.m..g|:Em.....:§ ...:..u.a, s3 2.3“ Emma .33 my? E... 3%.. E“. 87% mm 8 fl 3. 8 .3 .3 g 3 am {mm M mum ma <_ N_. ZU 26 ._.o m: m: in be On _ “n 3.2.3.: $3 $33 2.3 382193 3.33 52:. 588252 15% ._mw..~..,fl._;. Emu :Ew NEW”. . o 7..ww...-_._.lw.w 3 4n .8 U .3. 4m _ .8 .3 _ .5 .3 mo 9 mum mm. “ Om mm .5 T: ._.m __ in mm 0m __. .__“; b: In .2 Us. w. _u “M S33 3359323.3.59me avg. am..~p..§.m ._mNHNN.‘._.smmm,. magma mamgufiba NE.” Mama: 9:? . 13 m_ mm. .2 5m au__ \ mm . S3 3%? E: E2 $2 2 fl. 3:73.... «5.. .__ a. malaimw. a mailigm‘ _..mu_.__m-.mw Imwliiaw... |i...,.. “ Emmi;5.3.5...“ " Om F. _2a 3: may m: an ._d UU< hm :2» gas... :5... 23.1[meagefimfim _..m.fl.._~m.._.@.§. _.fi.s. as“? age 333 3.2. u g g _Ma.gmin.Hahn“ ._.= flm. C _2_u fl: >353 Gr 0* Wm 35 23 m as, 1 32% “3.8% 52m. 32% 33 3%. CE. ANS: u E: Ea E: Es “ v1.11...» ._. A. ...
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This note was uploaded on 04/24/2010 for the course CHEM 3331 taught by Professor Bean during the Fall '08 term at University of Houston.

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Test_II_3331_F - .._,-fi.-.“L“l \Nlm “53":L...

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