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exam-3 - CHEM 3332— EXAM 3 fining-VS A Nomenclature(3...

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Unformatted text preview: CHEM 3332— EXAM 3 fining-VS A. Nomenclature (3 points each; 9 total points) Please provide an acceptable name for each of the following compounds, noting stereochemistry where appropriate. M COOH Chem 833?. B. Facts (3 points each; 18 total points) 1 . Rank the pKa value of the following benzoic acids from lowest (1) to highest (3). OOH OOH OOH Br Br 2 . Rank the boiling points of the following molecules from lowest (1) to highest (3). o o H OH NH2 3 . Rank the indicated C—N bond lengths from shortest (1) to longest (3). I 0/ 0/ 4. Rank these molecules from slowest (1) to fastest (3) in their rate of nucleophilic acyl substitution. 0 o o H CI OCH3 5 . Circle only the most acidic hydrogen or hydrogens on each of the following molecules (i.e., one circle per molecule). /fi\ :E\ C) o o H 3 CH3 ‘ H3CCYfl\C’fl\CH3 HBC’fl\ ’CH3 2 I to 1'2 6 . Circle the more stable structure in each of the following pairs (i.e., one circle for each pair of structures). C. Reactions: Total = 30 points, 6 points each _ _ Please provide the starting material, the reagents, or major product in the answer box. Be sure your drawing indicates stereochemistry if applicable. Partial credit IS awarded only when intermediate products are shown below the reaction. 0 1. (CH3)2NH 2. H+ 1 O 3. SOCI 4. CH3CH20H 5. LlA|H4 (XS) 0 6. H20 1_CHgCEC‘Na+ H3C\ /CH3 2. 2. H30+ (I; 3. PCC CHS—C—CEC-CHS 4. Ph3P=C(CH3)2 1. CH3CH2Li (2 6(1) 2. H30" 3 W 3. NaCN/l-l+ or HCN ' 4. LiAlH4 ' O 1. $0012 or POCI3 4 g_NH2 2. CHacHgMgBr ' 3. H3O+ 4. Br2/acetic acid 5. 0% E (Dr/V D. Mechanism: Total = 18 points (9 points each) Provide clear mechanisms for reactions 1 and 2. Use curved arrow notaton to indicate "electron flow." Show all intermediates and all formal charges. if there is more than one resonance structure, you must show the "best" (Le. lowest energy) structure. 0 o E. Synthesis: 15 Points Synthesize the molecule below using any of the following reagents: benzene, cyclohexane, alcohols, alkanes, alkenes, and/or alkynes of two carbons or less, any Inorganic reagents, any oxidizing or reducing agents, and any peroxyacids. (I3H20H3 F. Spectroscopy: 10 Points A compound with the formula C6H1202 exhibits the IR, 1H NMR, and proton-decoupled 13C NMR spectra shown on the following page. Please identify this compound and draw the structure in the box provided below. X TRRNSHITTANCE 5.0 4.5 capillary film befuecn nl1‘ Plafes 4.0 3. 3.0 IO HAVEMJPBERS 2.5 2.0 1.5 1 v a Copyrlfl'lf 1992 1.!) PPM 0. TABLE 13.2 Characteristic infrared absorptions of groups ____________________._.__._——-———-— FREQUENCY GROUP RANGE (cm-1) INTENSITY“ ______________________-_——————————-—-— A. AJkyl C—H (stretching) 2853—2962 (m—s) Isopropyl, -—CI-I(CI-l,)2 1380-1385 (s) and 1365— 1370 (s) tart-Butyl, -—C(CH3)3 1385 - 1395 (m) and ~ 1365 (s) B. Alkenyl C—H (stretching) 3010—3095 (m) 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 hemmgs) 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—8 10 (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=C (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 GEN 2220-2260 (rn) " Abbreviations: s = strong, m = medium, w = weak, v = variable, ~ = approximately. 4.)um .w.w gnaoxmamnm U38: nzmafim. mjfim Hfivm Om ENOHOZ OImZHO>r m5: 3. 2.5: 1 25.. we? ST E No >5... ND?» 51: ._.>m_.m .wh >Unwox§mfim 8303-; 153:8. .213 we 2%. Pa: in: jam 9. 0:602 So: mamas? $5.4 S 3.3 >55 «canola? S: G 1 >59 we: OLE ~_fl No 2?. onw 81% was? was: 2 I? we Ext. wan? 3.8 w , _ _ 25; 5&an On 8:50. IDIX AX M Q. m: on Zlv 51am moaNén. 20m: NNINQ _ 33.0%. woman 5:: _ . . 2832 on 032. IOIO motoo a? 59%. wan; u. _ Lu _ mas. won—rm Snub >55. [mm 8-3 28:9. 59% mung / Ext 22:59 x05? {Tub >55 \nH a? so 2*: 023%. womb wolvm 535. Fans: $-90 2:. © 1 ”also 33:9 Pena: 3-3 _ 25:8. inmz no: Go w 0 >833 >5 2-8 >528. Iwirl Go- :5 Banana. xA—Wm cu 19m. 0 O Ouncoxén gnaw. 888. IWIO SCI ”mm 28:3 3903—. NOE oh I ob: >339 wlzmu 5:99. A__U was? Box 313‘. angina. .885. In! EVE nflcoxwzo. ”003 5.. 3.: EV l‘vlll‘ll'l'lll'lll .. .25 own—Enu— mamm cm 580 @883 <5 5 Q5083 875:; HE is. 833388 25 8:83.38? ...
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