2002 Final - F I Ina Exqm F21 2002 I A NOMENCLATURE(12...

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Unformatted text preview: F I . Ina/ Exqm F21] 2002 I A. NOMENCLATURE: (12 points, 3 pts. each) Give an acceptable IUPAC name for each of the following comp stereochemistry where appropriate. / / 1. CI / ounds. Be sure to indicate the Br 9H3 CH-CHCH3 2. I CH3 3. 4. B. Facts: Total = 18 points 1. Compare the reaction rates of reaction a) and reaction b) and place the letter of the faster re box provided. (2 pts.) action in the Br CH3OH _—_’ product D CH3OH b) /\/Br ’ product 2. Label the pair of molecules as identical, enantiomers, diastereomers, or structural isomers. (2 pts.) CH3 Cl Br —1—— OH Br —l—CH3 OH Cl 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.) 0 O gawk/CW": D U H H 4. Place the following carbocations invorder of increasing stability (1=least stable, 3=most stable). (3 pts.) OH OH + OH + + CE CH3 CH2 CH3 1 Cl 5. Place the following compounds in order of increasing frequency of the bond stretching vibration indicated by the arrow. (1 = lowest frequency, 3 = highest frequency) (3 pts.) jl f D f i: 6. Label the alkenes as stable or unstable. (3 pts.) 7. Whichof the isomers undergoes the E2 process more rapidly? Place the letter of the isomer in the box provnded. (2 pts.) Cl C(CH3)3 C(C Hals Answer: [:1 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. O':> 1) NaOCHZCHg ': 2) H2, Pt (catalyst) 1) NBS, light 2) /: 2) Mg, ether 3) 0:0 4) H3069 3) 9H Bra H3::CHZCH3 H3 1 H H20 (solvent) 5 5) OH D 1) PC|3 2) @9 K 0+ 1) Hg(OAc)2, H20 2) NaBH4 1) Brg, light 2) NaOCH3 3) HBr, R-O-O-R 10) PCC: pyridinium ch|orochromate 1) KMnO4, Hf, Heat 2) NaBH4 D. Mechanism: 10 points For the following reaction, propose a detailed, step by step mechanism to explain the formation of the product. Show all intermediates and formal charges, and use curved arrows to indicate electron flow. OH 0 CH3 0 I l n O OH C—CH l 3 H2304 HOCHg—C—C-CHs \C_CH_C';_CH3 \ CH3 -—'————'> H l ' 100°C (j 00.43 + E. SYNTHESS (10 points) From cyclohexane, methanol, and any inorganic reagents, synthesize the compound below. 0% F. SPECTROSCOPY (10 points) Carefully examine th e five infrared spectra and the compounds below. Place the letter of the compound in the box beside its spectrum. N HO CH3 ll NHZ )l OH 0 o o s CH3 CH3 0 C B D E F G Wavelength turn) 8 9 1 l 0 T 8000 l" l 2200 2000 1800 1600 1400 1200 1000 l r r 2600 l 00 3500 800 +300 40 ‘ . Wavenumber ‘ cm’ 13 Micrometers 6 7 3200 2800 1800 1600 1400 1200 1000 3600 Wavenumber (cm‘l) ’l‘ransmittance (‘70) Wavelength (p.111) 89 __s 6 7 __1‘1 10 ,1— : 1 s | 1 l I 3000 2600 2200 2000 1800 1600 1400 1200 Wavenumber (cm‘ 1) 4000 3500 0,, "11,.1.» 1,. ,_, _ , _, "1 mummmmmmmmmwm ‘-‘( 1000 80“ ‘5 1| ‘7 1| II J. ,1, L.l_J L Aw ,‘ 4‘11‘ _.. [O _J _L_.,AV1LV_J 1 LwA ._._Vd__.1n.. TABLE 13.2 Characteristic infrared absorptions of groups FREQUENCY GROUP RANGE (cm") INTENSI’IY“ A. Alkyl C—l—l (so-etching) 2853 ~2962 (m—s) Isopropyl, --'CI-I(Cl—13)2 1380-1385 (s) and 1365—1370 (s) ren-Butyl, —C(CH3)3 1385—1395 (m) and ~ 1365 (S) B. Alkenyl C—H (stretching) 3010—3095 (to) C==C (stretching) 1620- 1680 (v) R—CH=CH2 985— 1000 (s) and 905 -920 (s) RIC =CH-_, (out-of—plane 880—900 (s) cis-RCH=CHR C_H benmngs’ 675 —730 (s) trans-RCH=CHR 960—975 (s) C. Alkynyl —=-‘—C-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 V, 690—710 (very s) and 730—770 (very s) o Disubstituted 735-770 (5) m Disubstituted 680—725 (s) and 750-810 (very s) p Disubstituted 800—840 (very s) E Alcohols, Phenols, and Carboxyhc 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 (snatching) 1630-1780 (5) Aldehydes 1690- 1740 (s) Ketones 1680— 1750 (s) Esters 1735—1750 (5) Carboxylic acids 1710_1780 (S) Amides 1630- 1690 (s) G. Amines N—H 3300-3500 (m) H. Nitriles CEN 2220-2260 (m) ___’______________—________.—_——— ° Abbreviations: s = strong, at = medium, w = weak. v = variable, ~ = approximately. ...
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2002 Final - F I Ina Exqm F21 2002 I A NOMENCLATURE(12...

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