final exam 2 - m We M3959 Final Exam Name(PRINT Last First...

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Unformatted text preview: m We M3959 Final Exam Name (PRINT) Last, First Chemistry 3331 Signature December 10, 2002 SS# Please circle the name of your professor and class time where appropriate. Dr. Bean (TIT h 1 0 AM) Dr. Cai Dr. Bean (TIT h 5:30 PM) A. NOMENCLATURE: (12 points, 3 pts. each) Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. Cl/ Br CH3 I CH-CHCH3 | CH3 HO B. Facts: Total = 18 points 1. Compare the reaction rates of reaction a) and reaction b) and place the letter of the faster reaction in the box provided. (2 pts.) Br CH30H a) ’ product CH30H 1:! b) /\/B’ "“""" product 2. Label the pair of molecules as identical, enantiomers CH3 Cl Br +OH Br +CH3 Cl OH 3. Place the hydrogens indicated in order of increasing acidity by placing the appropriate number in the box below each arrow. (1 = least acidic, 3 = most acidic) (3 pts -) , diastereomers, or structural isomers. (2 pts.) 0 O WCWD flack/L? DD 4. Place the following carbocations in order of increasing stability (1=least stable, 3=moSt stable). (3 pts.) OH OH + OH E 1+ + [ I CH3 D D D 5. Place the following compounds in order of increasing frequency of th e bond stretching vibration indicated by the arrow. (1 = lowest frequency, 3 = highest frequency) (3 pts.) D D 6. Label the alkenes as stable or unstable. (3 pts.) 7. Which of the isomers undergoes the E2 process more rapidly? Place the letter of the isomer in the box provided. (2 pts.) c: C(CH3)3 Q‘mwm b Cl Answer: El C. REACTIONS: (40 points, 4 pts. each) Please give the final major product, the reagents, or the starting material for each of the following reactions in the box provided. Be sure your answers indicate stereochemistry where appropriate. Intermediate products may be placed below the reaction for partial credit but not in the answer box. Br Cb 1) NaOCHZCHs —; 2) H2, Pt (catalyst) H 1)NBS, light 2) /: 2) Mg, ether 4) H306) 3) 9” Br2 ngiCHZCHs H3 . H H20 (solvent) é 6) 7) OH 1) PC|3 2) 699 K 0+ 1) Hg(OAC)2, H20 2) NaBH4 1) Brg, light 2) NaOCH3 3) HBr, R-O-O-R H H SH 8) 10) 1) >~MgBr 2) H 2804, heat 3) o3 4) (CH3)2S 1) PCC ® 2) H—Ee Na OH . 0A 3) SlagBH 4) H202, NaOH PCC: pyridinium chlorochromate 1) KMnO4, Hf, Heat 2) NaBH4 ) D. Mechanism: 10 points For the following reaction, propose a detailed, ste p by step mechanism to explain the formation of the product. Show all intermediates and formal charg es, and use curved arrows to indicate electron flow. 0 CIJH CH3 0 (:—CH3 ' " \ . I H2804 HOCH2— C—C-CHs [c — CH—c-CH3 0\ OH CH3 “—p H cH 100°C (j 3 + E. SYNTHESS (10 points) From cyclohexane, methanol, and any inorganic reagents, synthesize the compound below. cm Transmittance (%) $88 4000 3600 3200 2800 2400 2000 1800 l 600 F. SPECTROSCOPY (10 points) Carefully examine the five infrared spectra and the compounds below. Place the letter of the compound in the box beside its spectrum. N HO CH3 H H : O 0 CH3 CH3 A B C D Wavelength (pm) “.5 3 4 5 6 7 8 9 10 NH2 | | l l l l l | l | 4000 3500 3000 2600 2200 2000 1800 1600 1400 1200 1000 Wavenumber (cm‘ 1) Micrometers 7 2.5 6 1400 Wavenumber (cm'l) 1200 800 10 1000 11 600 OH Wavelength ( mu) 7 Ru 2.5 O 0 0 0 O m 8 6 4 2 GS woswufifimsmfi. 0 6( 800 3000 2600 2200 2000 1800 1600 1400 1200 1000 3500 4000 1) Wavenumber (cm‘ '8 II . .Hx , 1. 1| I1 1 1 ., ~ .V. 1 9 ‘0 ”W- ‘1 v.1, 4 NICOLET IO TABLE 13.2 Characteristic infrared absorptions of groups _________________.__._____—————-—- FREQUENCY GROUP RANGE (cm' ‘) INTENSITY” _______________________.___..__————————————-——— A. Alkyl C—H (stretching) 285352962 (m-s) lsopropyl, —CH(CH3)2 1380—1385 (s) and 1365— 1370 (s) ten-Butyl, —-C(Cl-l3)3 1385- 1395 (m) and ~ 1365 (s) B. Alkenyl C—H (stretching) 3010—3095 (111) C =C (stretching) 1620— 1680 (v) R—CH=CH2 985— 1000 (s) and 905 -—920 (s) R2C=CH2 (out—of-plane 880—900 (s) cis-RCH=CHR C-H bendmgs) 675 —730 (s) trans-RCH=CHR 960—975 (s) C. Alkynyl EC—H (stretching) ~ 3300 (s) CEC (stretching) 2100—2260 (v) D. Aromatic Ar—H (stretching) ~ 3030 (v) Aromatic substitution type (C --H out-of-plane bendings) Monosubstituted ., 690—710 (very s) and 730—770 (very s) o Disubstituted 735—770 (s) m Disubstituted 680—725 (s) and 750—810 (very s) p Disubstituted ‘ 800—840 (very s) E. Alcohols, Phenols, and Carboxylic Acids 0—H (stretching) Alcohols, phenols (dilute solutions) 3590—3650 (sharp, V) Alcohols, phenols (hydrogen bonded) 3200—3550 (broad, s) Carboxylic acids (hydrogen bonded) 2500-3000 (broad, v) F. Aldehydes, Ketones, Esters, and Carboxylic Acids C=O (stretching) 1630—1780 (s) Aldehydes 1690— 1740 (s) Ketones 1680— 1750 (s) Esters 1735— 1750 (s) Carboxylic acids 1710—1780 (s) Amides 1630— 1690 (s) G. Amines N—H 3300—3500 (In) H. Nitriles C EN 2220-2260 (In) “ Abbreviations: s = strong. m = medium, w = weak. v = variable. ~ = approximately. Ema—06.0 .3me 01 ._._._m mrmgmza >33? 5:372 22.5 3215. >33mn $35.... 5 2.5.5:! >_ 2.3: 3.33 w» #5535 .2 3.8 3 Nag—83...... . 12...?! x 3.3» U: dz... fin 5.8 a. 3.3.5.. 1: Es anal—Ea 1...: n? 5.8 535:: 2.5-2.3 3.25:: an :38 53...... In :2. a .2: a .3 .: , . u o a. 422:! 5.22:! regal M, grassfiaao «nan... as H .2. F: Gabi :93 w . 2...:an .a 133:5.»- IR 3-: 35:3: 9.. =5 :3... 52a 2. warrant: .88... 2 92:33:. 0.25:... ...
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